Add LLM digest setup and share timestamp context

2026-05-19 19:17:35 +02:00
parent 9d2da0c600
commit 5d80af375e
42 changed files with 2878 additions and 39 deletions
@@ -52,6 +52,9 @@ Notable build-time flags live in `lib/core/config/app_config.dart`:
 - `BACKGROUND_SYNC_INTERVAL_SECONDS`
 - `ENABLE_LOCAL_NOTIFICATIONS`
 - `ENABLE_WHATSAPP_SHARE_INTAKE`
+- `SENTRY_DSN` defaults to the Bugsink project DSN
+- `SENTRY_ENVIRONMENT`
+- `SENTRY_RELEASE`

 ## Run

@@ -75,6 +78,14 @@ flutter run \
  --dart-define=BACKEND_BASE_URL=https://api.example.com
 ```

+Build a release with explicit Bugsink/Sentry metadata:
+
+```bash
+flutter build apk --release \
+  --dart-define=SENTRY_ENVIRONMENT=production \
+  --dart-define=SENTRY_RELEASE=relationship_saver@1.0.0+1
+```
+
 Run tests:

 ```bash
@@ -1,9 +1,11 @@
 <manifest xmlns:android="http://schemas.android.com/apk/res/android">
+    <uses-permission android:name="android.permission.INTERNET" />
    <uses-permission android:name="android.permission.POST_NOTIFICATIONS" />
    <application
        android:label="relationship_saver"
        android:name="${applicationName}"
-        android:icon="@mipmap/ic_launcher">
+        android:icon="@mipmap/ic_launcher"
+        android:usesCleartextTraffic="true">
        <activity
            android:name=".MainActivity"
            android:exported="true"
@@ -14,6 +14,33 @@ Runtime override (for future settings screens):
 AppConfig.overrideBackendBaseUrl('https://staging.example.com');
 ```

+## Bugsink Error Tracking
+
+Release builds initialize `sentry_flutter` with the project Bugsink DSN by
+default. Bugsink is Sentry API compatible, so the app uses the normal Sentry
+Flutter SDK.
+
+The default DSN is:
+
+```text
+https://97fb0a56bc35440fba0ba139dc3b1ccc@bugs.zuzo.ch/2
+```
+
+Override metadata at build time when needed:
+
+```bash
+flutter build apk --release \
+  --dart-define=SENTRY_ENVIRONMENT=production \
+  --dart-define=SENTRY_RELEASE=relationship_saver@1.0.0+1
+```
+
+To point a build at a different Sentry-compatible project:
+
+```bash
+flutter build apk --release \
+  --dart-define=SENTRY_DSN=https://public-key@example.com/1
+```
+
 ## Run With Fake Gateway

 Use fake gateway for local/offline development:
@@ -21,6 +21,8 @@ PODS:
  - shared_preferences_foundation (0.0.1):
    - Flutter
    - FlutterMacOS
+  - url_launcher_ios (0.0.1):
+    - Flutter
  - workmanager_apple (0.0.1):
    - Flutter

@@ -34,6 +36,7 @@ DEPENDENCIES:
  - receive_sharing_intent (from `.symlinks/plugins/receive_sharing_intent/ios`)
  - sentry_flutter (from `.symlinks/plugins/sentry_flutter/ios`)
  - shared_preferences_foundation (from `.symlinks/plugins/shared_preferences_foundation/darwin`)
+  - url_launcher_ios (from `.symlinks/plugins/url_launcher_ios/ios`)
  - workmanager_apple (from `.symlinks/plugins/workmanager_apple/ios`)

 SPEC REPOS:
@@ -59,6 +62,8 @@ EXTERNAL SOURCES:
    :path: ".symlinks/plugins/sentry_flutter/ios"
  shared_preferences_foundation:
    :path: ".symlinks/plugins/shared_preferences_foundation/darwin"
+  url_launcher_ios:
+    :path: ".symlinks/plugins/url_launcher_ios/ios"
  workmanager_apple:
    :path: ".symlinks/plugins/workmanager_apple/ios"

@@ -73,6 +78,7 @@ SPEC CHECKSUMS:
  Sentry: da60d980b197a46db0b35ea12cb8f39af48d8854
  sentry_flutter: 27892878729f42701297c628eb90e7c6529f3684
  shared_preferences_foundation: 7036424c3d8ec98dfe75ff1667cb0cd531ec82bb
+  url_launcher_ios: 7a95fa5b60cc718a708b8f2966718e93db0cef1b
  workmanager_apple: 904529ae31e97fc5be632cf628507652294a0778

 PODFILE CHECKSUM: 1959d098c91d8a792531a723c4a9d7e9f6a01e38
@@ -43,6 +43,13 @@
 	<string>$(FLUTTER_BUILD_NUMBER)</string>
 	<key>LSRequiresIPhoneOS</key>
 	<true/>
+	<key>NSAppTransportSecurity</key>
+	<dict>
+		<key>NSAllowsLocalNetworking</key>
+		<true/>
+	</dict>
+	<key>NSLocalNetworkUsageDescription</key>
+	<string>Relationship Saver can connect to your local Ollama server for private AI suggestions.</string>
 	<key>NSPhotoLibraryUsageDescription</key>
 	<string>Relationship Saver can import shared media and links you send into the app.</string>
 	<key>UIApplicationSceneManifest</key>
@@ -66,7 +66,7 @@ extension LocalRepositoryAiDigestOperations on LocalRepository {
              ? IdeaType.gift
              : IdeaType.event,
          title: draft.title,
-          details: _aiDraftDetails(draft),
+          details: _aiIdeaDetails(draft),
          createdAt: now,
        );
        await _setState(
@@ -156,6 +156,18 @@ String _aiDraftDetails(AiSuggestionDraft draft) {
  return '${draft.details.trim()}$reason'.trim();
 }

+String _aiIdeaDetails(AiSuggestionDraft draft) {
+  final List<String> parts = <String>[
+    _aiDraftDetails(draft),
+    if (draft.eventLocation != null && draft.eventLocation!.trim().isNotEmpty)
+      'Location: ${draft.eventLocation!.trim()}',
+    if (draft.eventUrl != null && draft.eventUrl!.trim().isNotEmpty)
+      'Event: ${draft.eventUrl!.trim()}',
+    if (draft.sourceUrls.isNotEmpty) 'Sources: ${draft.sourceUrls.join(', ')}',
+  ].where((String value) => value.trim().isNotEmpty).toList(growable: false);
+  return parts.join('\n\n').trim();
+}
+
 extension<T> on Iterable<T> {
  T? get firstOrNull => isEmpty ? null : first;
 }
@@ -12,6 +12,7 @@ extension LocalRepositoryShareOperations on LocalRepository {
      rawText: input.messageText.trim(),
      createdAt: input.sharedAt ?? now,
      receivedAt: now,
+      sharedMessageDateTime: input.sharedAt,
      platform: 'legacy',
      sourceDisplayName: _trimToNull(input.sourceDisplayName),
      sourceUserId: _trimToNull(input.sourceUserId),
@@ -390,7 +391,8 @@ extension LocalRepositoryShareOperations on LocalRepository {
    String? consumedInboxEntryId,
  }) async {
    final String sourceApp = payload.sourceApp;
-    final DateTime sharedAt = payload.createdAt;
+    final DateTime sharedAt =
+        payload.sharedMessageDateTime ?? payload.createdAt;
    final String? sourceUserId = payload.sourceUserId;
    final String? sourceThreadId = payload.sourceThreadId;
    final bool createdSourceLink = matchedLink == null;
@@ -11,6 +11,17 @@ class AppConfig {

  static const String _defaultSentryDsn = String.fromEnvironment(
    'SENTRY_DSN',
+    defaultValue:
+        'https://97fb0a56bc35440fba0ba139dc3b1ccc@bugs.zuzo.ch/2',
+  );
+
+  static const String _defaultSentryEnvironment = String.fromEnvironment(
+    'SENTRY_ENVIRONMENT',
+    defaultValue: '',
+  );
+
+  static const String _defaultSentryRelease = String.fromEnvironment(
+    'SENTRY_RELEASE',
    defaultValue: '',
  );

@@ -53,9 +64,27 @@ class AppConfig {
    defaultValue: 180,
  );

-  /// Optional Sentry DSN for release crash/error reporting.
+  /// Sentry-compatible DSN for release crash/error reporting.
  static String get sentryDsn => _defaultSentryDsn.trim();

+  /// Sentry environment label.
+  static String get sentryEnvironment {
+    final String configured = _defaultSentryEnvironment.trim();
+    if (configured.isNotEmpty) {
+      return configured;
+    }
+    return useFakeBackend ? 'development' : 'production';
+  }
+
+  /// Optional Sentry release identifier.
+  static String? get sentryRelease {
+    final String configured = _defaultSentryRelease.trim();
+    if (configured.isEmpty) {
+      return null;
+    }
+    return configured;
+  }
+
  /// Runtime override for backend URL (e.g. local settings screen).
  static void overrideBackendBaseUrl(String? baseUrl) {
    _baseUrlOverride = baseUrl;
@@ -0,0 +1,118 @@
+import 'dart:convert';
+
+import 'package:flutter_riverpod/flutter_riverpod.dart';
+import 'package:shared_preferences/shared_preferences.dart';
+
+const String _llmDiagnosticsLogKey = 'llm_diagnostics_log_v1';
+const int _maxLlmDiagnosticsEvents = 40;
+const int _maxLlmDiagnosticsDetailChars = 8000;
+
+class LlmDiagnosticsEvent {
+  const LlmDiagnosticsEvent({
+    required this.at,
+    required this.stage,
+    required this.message,
+    this.details,
+  });
+
+  factory LlmDiagnosticsEvent.fromJson(Map<String, dynamic> json) {
+    return LlmDiagnosticsEvent(
+      at: DateTime.parse(
+        json['at'] as String? ?? DateTime.now().toUtc().toIso8601String(),
+      ).toLocal(),
+      stage: json['stage'] as String? ?? 'unknown',
+      message: json['message'] as String? ?? '',
+      details: json['details'] as String?,
+    );
+  }
+
+  final DateTime at;
+  final String stage;
+  final String message;
+  final String? details;
+
+  Map<String, dynamic> toJson() {
+    return <String, dynamic>{
+      'at': at.toUtc().toIso8601String(),
+      'stage': stage,
+      'message': message,
+      if (details != null) 'details': details,
+    };
+  }
+}
+
+class LlmDiagnosticsLog {
+  const LlmDiagnosticsLog();
+
+  Future<List<LlmDiagnosticsEvent>> read() async {
+    final SharedPreferences prefs = await SharedPreferences.getInstance();
+    final String? raw = prefs.getString(_llmDiagnosticsLogKey);
+    if (raw == null || raw.isEmpty) {
+      return const <LlmDiagnosticsEvent>[];
+    }
+    try {
+      final List<dynamic> items = jsonDecode(raw) as List<dynamic>;
+      return items
+          .whereType<Map<String, dynamic>>()
+          .map(LlmDiagnosticsEvent.fromJson)
+          .toList(growable: false);
+    } on FormatException {
+      return const <LlmDiagnosticsEvent>[];
+    }
+  }
+
+  Future<void> record(String stage, String message, {String? details}) async {
+    final SharedPreferences prefs = await SharedPreferences.getInstance();
+    final List<LlmDiagnosticsEvent> current = await read();
+    final List<LlmDiagnosticsEvent> next = <LlmDiagnosticsEvent>[
+      LlmDiagnosticsEvent(
+        at: DateTime.now(),
+        stage: stage,
+        message: message,
+        details: _compactDetails(details),
+      ),
+      ...current,
+    ].take(_maxLlmDiagnosticsEvents).toList(growable: false);
+    await prefs.setString(
+      _llmDiagnosticsLogKey,
+      jsonEncode(
+        next
+            .map((LlmDiagnosticsEvent event) => event.toJson())
+            .toList(growable: false),
+      ),
+    );
+  }
+
+  Future<void> clear() async {
+    final SharedPreferences prefs = await SharedPreferences.getInstance();
+    await prefs.remove(_llmDiagnosticsLogKey);
+  }
+
+  String exportText(List<LlmDiagnosticsEvent> events) {
+    if (events.isEmpty) {
+      return 'No LLM diagnostics recorded.';
+    }
+    return events
+        .map((LlmDiagnosticsEvent event) {
+          final String details = event.details == null
+              ? ''
+              : '\n${event.details}';
+          return '[${event.at.toIso8601String()}] ${event.stage}: ${event.message}$details';
+        })
+        .join('\n\n');
+  }
+}
+
+final Provider<LlmDiagnosticsLog> llmDiagnosticsLogProvider =
+    Provider<LlmDiagnosticsLog>((Ref ref) => const LlmDiagnosticsLog());
+
+String? _compactDetails(String? value) {
+  final String? trimmed = value?.trim();
+  if (trimmed == null || trimmed.isEmpty) {
+    return null;
+  }
+  if (trimmed.length <= _maxLlmDiagnosticsDetailChars) {
+    return trimmed;
+  }
+  return '${trimmed.substring(0, _maxLlmDiagnosticsDetailChars)}\n[truncated]';
+}
@@ -4,6 +4,9 @@ import 'package:dio/dio.dart';
 import 'package:flutter_riverpod/flutter_riverpod.dart';
 import 'package:relationship_saver/core/llm/captured_fact_draft_parser.dart';
 import 'package:relationship_saver/core/llm/llm_config.dart';
+import 'package:relationship_saver/core/llm/llm_diagnostics_log.dart';
+import 'package:relationship_saver/core/llm/ollama/ollama_tool_chat_client.dart';
+import 'package:relationship_saver/core/observability/sentry_init.dart';
 import 'package:relationship_saver/features/people/domain/person_models.dart';
 import 'package:relationship_saver/features/share_intake/domain/share_models.dart';

@@ -100,6 +103,7 @@ Generate 3-5 helpful relationship signals for these people.''';
  Future<String> completeText({
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  }) async {
    final config = await _config;
    final String? apiKey = await _ref
@@ -117,6 +121,7 @@ Generate 3-5 helpful relationship signals for these people.''';
      model: config.model,
      systemPrompt: systemPrompt,
      userPrompt: userPrompt,
+      enableWebSearch: enableWebSearch,
    );
  }

@@ -147,6 +152,9 @@ Be conservative. If the content is ambiguous, prefer "note". Return JSON only.''
 Sender: ${payload.sourceDisplayName ?? "unknown"}
 Platform: ${payload.platform}
 URL: ${payload.url ?? "none"}
+shared_message_datetime: ${payload.sharedMessageDateTime?.toIso8601String() ?? "null"}
+Import received at: ${payload.receivedAt.toIso8601String()}
+If shared_message_datetime is present, use it as the point-in-time reference for interpreting the message. Old status or health updates should usually become historical context or durable preferences, not current check-in prompts.
 Raw text:
 ${payload.rawText}''';

@@ -230,14 +238,30 @@ ${payload.rawText}''';
    required String model,
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  }) async {
-    final Dio dio = _createDio();
+    final Dio dio = provider == LlmProvider.ollama
+        ? _createDio(receiveTimeout: const Duration(minutes: 5))
+        : _createDio();
    final String resolvedBaseUrl = _normalizeBaseUrl(baseUrl);
+    await _recordDiagnostics(
+      'request_start',
+      'Starting ${provider.label} LLM request.',
+      details: _diagnosticsDetails(
+        provider: provider,
+        baseUrl: resolvedBaseUrl,
+        model: model,
+        enableWebSearch: enableWebSearch,
+        systemPrompt: systemPrompt,
+        userPrompt: userPrompt,
+      ),
+    );

    try {
+      late final String content;
      switch (provider) {
        case LlmProvider.openai:
-          return _callOpenAI(
+          content = await _callOpenAI(
            dio,
            resolvedBaseUrl,
            apiKey,
@@ -246,7 +270,7 @@ ${payload.rawText}''';
            userPrompt,
          );
        case LlmProvider.anthropic:
-          return _callAnthropic(
+          content = await _callAnthropic(
            dio,
            resolvedBaseUrl,
            apiKey,
@@ -255,24 +279,26 @@ ${payload.rawText}''';
            userPrompt,
          );
        case LlmProvider.google:
-          return _callGoogleAI(
+          content = await _callGoogleAI(
            dio,
            resolvedBaseUrl,
            apiKey,
            model,
            systemPrompt,
            userPrompt,
+            enableWebSearch: enableWebSearch,
          );
        case LlmProvider.ollama:
-          return _callOllama(
+          content = await _callOllama(
            dio,
            resolvedBaseUrl,
            model,
            systemPrompt,
            userPrompt,
+            enableWebSearch: enableWebSearch,
          );
        case LlmProvider.openaiCompatible:
-          return _callOpenAI(
+          content = await _callOpenAI(
            dio,
            resolvedBaseUrl,
            apiKey,
@@ -281,11 +307,88 @@ ${payload.rawText}''';
            userPrompt,
          );
      }
+      await _recordDiagnostics(
+        'request_success',
+        '${provider.label} returned a response.',
+        details: _diagnosticsDetails(
+          provider: provider,
+          baseUrl: resolvedBaseUrl,
+          model: model,
+          enableWebSearch: enableWebSearch,
+          systemPrompt: systemPrompt,
+          userPrompt: userPrompt,
+          responseLength: content.length,
+        ),
+      );
+      return content;
    } on DioException catch (error) {
+      await _recordProviderFailure(
+        provider: provider,
+        baseUrl: resolvedBaseUrl,
+        model: model,
+        enableWebSearch: enableWebSearch,
+        systemPrompt: systemPrompt,
+        userPrompt: userPrompt,
+        error: error,
+      );
      throw _mapProviderError(provider, error);
    }
  }

+  Future<void> _recordDiagnostics(
+    String stage,
+    String message, {
+    String? details,
+  }) async {
+    try {
+      await _ref
+          .read(llmDiagnosticsLogProvider)
+          .record(stage, message, details: details);
+    } catch (_) {
+      // Diagnostics must never break the user-facing LLM flow.
+    }
+  }
+
+  Future<void> _recordProviderFailure({
+    required LlmProvider provider,
+    required String baseUrl,
+    required String model,
+    required bool enableWebSearch,
+    required String systemPrompt,
+    required String userPrompt,
+    required DioException error,
+  }) {
+    final int? statusCode = error.response?.statusCode;
+    final String status = statusCode == null
+        ? 'without HTTP status'
+        : '$statusCode';
+    final Map<String, dynamic> context = _diagnosticsMap(
+      provider: provider,
+      baseUrl: baseUrl,
+      model: model,
+      enableWebSearch: enableWebSearch,
+      systemPrompt: systemPrompt,
+      userPrompt: userPrompt,
+      dioType: error.type.name,
+      statusCode: statusCode,
+      providerMessage: _extractProviderMessage(error.response?.data),
+      responseBody: _safeJson(error.response?.data),
+    );
+    _ref
+        .read(sentryInitProvider)
+        .captureException(
+          error,
+          stackTrace: error.stackTrace,
+          area: 'llm_provider',
+          context: context,
+        );
+    return _recordDiagnostics(
+      'provider_error',
+      '${provider.label} request failed with $status.',
+      details: const JsonEncoder.withIndent('  ').convert(context),
+    );
+  }
+
  Future<String> _callOpenAI(
    Dio dio,
    String baseUrl,
@@ -364,8 +467,9 @@ ${payload.rawText}''';
    String? apiKey,
    String model,
    String systemPrompt,
-    String userPrompt,
-  ) async {
+    String userPrompt, {
+    bool enableWebSearch = false,
+  }) async {
    final String modelPath = model.startsWith('models/')
        ? model
        : 'models/$model';
@@ -387,6 +491,10 @@ ${payload.rawText}''';
                ],
              },
            ],
+            if (enableWebSearch)
+              'tools': [
+                {'google_search': <String, dynamic>{}},
+              ],
            'generationConfig': {'temperature': 0.7, 'maxOutputTokens': 1000},
          }),
        );
@@ -409,8 +517,20 @@ ${payload.rawText}''';
    String baseUrl,
    String model,
    String systemPrompt,
-    String userPrompt,
-  ) async {
+    String userPrompt, {
+    bool enableWebSearch = false,
+  }) async {
+    if (enableWebSearch) {
+      return _ref
+          .read(ollamaToolChatClientProvider)
+          .complete(
+            baseUrl: baseUrl,
+            model: model,
+            systemPrompt: systemPrompt,
+            userPrompt: userPrompt,
+          );
+    }
+
    final Response<Map<String, dynamic>> response = await dio
        .post<Map<String, dynamic>>(
          '$baseUrl/api/chat',
@@ -609,6 +729,97 @@ LlmProviderException _mapProviderError(
  );
 }

+String _diagnosticsDetails({
+  required LlmProvider provider,
+  required String baseUrl,
+  required String model,
+  required bool enableWebSearch,
+  required String systemPrompt,
+  required String userPrompt,
+  int? responseLength,
+  String? dioType,
+  int? statusCode,
+  String? providerMessage,
+  String? responseBody,
+}) {
+  return const JsonEncoder.withIndent('  ').convert(
+    _diagnosticsMap(
+      provider: provider,
+      baseUrl: baseUrl,
+      model: model,
+      enableWebSearch: enableWebSearch,
+      systemPrompt: systemPrompt,
+      userPrompt: userPrompt,
+      responseLength: responseLength,
+      dioType: dioType,
+      statusCode: statusCode,
+      providerMessage: providerMessage,
+      responseBody: responseBody,
+    ),
+  );
+}
+
+Map<String, dynamic> _diagnosticsMap({
+  required LlmProvider provider,
+  required String baseUrl,
+  required String model,
+  required bool enableWebSearch,
+  required String systemPrompt,
+  required String userPrompt,
+  int? responseLength,
+  String? dioType,
+  int? statusCode,
+  String? providerMessage,
+  String? responseBody,
+}) {
+  final Map<String, dynamic> diagnostics = <String, dynamic>{
+    'provider': provider.name,
+    'baseUrl': baseUrl,
+    'model': model,
+    'webSearchRequested': enableWebSearch,
+    'systemPromptChars': systemPrompt.length,
+    'userPromptChars': userPrompt.length,
+  };
+  if (responseLength != null) {
+    diagnostics['responseChars'] = responseLength;
+  }
+  if (dioType != null) {
+    diagnostics['dioType'] = dioType;
+  }
+  if (statusCode != null) {
+    diagnostics['statusCode'] = statusCode;
+  }
+  if (providerMessage != null) {
+    diagnostics['providerMessage'] = providerMessage;
+  }
+  if (responseBody != null) {
+    diagnostics['responseBody'] = responseBody;
+  }
+  return diagnostics;
+}
+
+String? _safeJson(Object? data) {
+  if (data == null) {
+    return null;
+  }
+  try {
+    final String encoded = data is String
+        ? data
+        : const JsonEncoder.withIndent('  ').convert(data);
+    return _compactDiagnosticValue(encoded);
+  } catch (_) {
+    return _compactDiagnosticValue('$data');
+  }
+}
+
+String _compactDiagnosticValue(String value) {
+  final String compacted = value.trim().replaceAll(RegExp(r'\s+'), ' ');
+  if (compacted.length <= 3000) {
+    return compacted;
+  }
+  return '${compacted.substring(0, 2997)}...';
+}
+
 String _normalizeBaseUrl(String baseUrl) {
  String normalized = baseUrl.trim();
  while (normalized.endsWith('/')) {
@@ -617,11 +828,11 @@ String _normalizeBaseUrl(String baseUrl) {
  return normalized;
 }

-Dio _createDio() {
+Dio _createDio({Duration receiveTimeout = const Duration(seconds: 20)}) {
  return Dio(
    BaseOptions(
      connectTimeout: const Duration(seconds: 20),
-      receiveTimeout: const Duration(seconds: 20),
+      receiveTimeout: receiveTimeout,
      sendTimeout: const Duration(seconds: 20),
    ),
  );
@@ -0,0 +1,261 @@
+import 'dart:convert';
+
+import 'package:dio/dio.dart';
+import 'package:flutter_riverpod/flutter_riverpod.dart';
+import 'package:relationship_saver/core/llm/ollama/ollama_web_search_client.dart';
+
+class OllamaToolChatClient {
+  OllamaToolChatClient({
+    required OllamaWebSearchClient webSearchClient,
+    Dio? dio,
+    int maxToolRounds = 3,
+  }) : _webSearchClient = webSearchClient,
+       _dio = dio ?? _createDio(),
+       _maxToolRounds = maxToolRounds;
+
+  final OllamaWebSearchClient _webSearchClient;
+  final Dio _dio;
+  final int _maxToolRounds;
+
+  Future<String> complete({
+    required String baseUrl,
+    required String model,
+    required String systemPrompt,
+    required String userPrompt,
+  }) async {
+    final List<Map<String, dynamic>> messages = <Map<String, dynamic>>[
+      {'role': 'system', 'content': _toolSystemPrompt(systemPrompt)},
+      {'role': 'user', 'content': userPrompt},
+    ];
+
+    String latestContent = '';
+    for (int round = 0; round <= _maxToolRounds; round += 1) {
+      final Map<String, dynamic> message = await _chat(
+        baseUrl: baseUrl,
+        model: model,
+        messages: messages,
+      );
+      latestContent = _stringValue(message['content']);
+
+      final List<Map<String, dynamic>> toolCalls = _toolCalls(message);
+      if (toolCalls.isEmpty) {
+        return latestContent;
+      }
+
+      messages.add(<String, dynamic>{
+        'role': 'assistant',
+        'content': latestContent,
+        'tool_calls': toolCalls,
+      });
+
+      for (final Map<String, dynamic> toolCall in toolCalls) {
+        final String toolName = _toolName(toolCall);
+        final Map<String, dynamic> arguments = _toolArguments(toolCall);
+        final String toolResult = await _executeTool(toolName, arguments);
+        messages.add(<String, dynamic>{
+          'role': 'tool',
+          'tool_name': toolName,
+          'content': toolResult,
+        });
+      }
+    }
+
+    if (latestContent.trim().isNotEmpty) {
+      return latestContent;
+    }
+    throw StateError(
+      'Ollama did not return a final response after tool calls.',
+    );
+  }
+
+  Future<Map<String, dynamic>> _chat({
+    required String baseUrl,
+    required String model,
+    required List<Map<String, dynamic>> messages,
+  }) async {
+    final Response<Map<String, dynamic>> response = await _dio
+        .post<Map<String, dynamic>>(
+          '$baseUrl/api/chat',
+          options: Options(headers: {'Content-Type': 'application/json'}),
+          data: jsonEncode(<String, dynamic>{
+            'model': model,
+            'stream': false,
+            'messages': messages,
+            'tools': _tools,
+          }),
+        );
+    final Map<String, dynamic> data = response.data ?? <String, dynamic>{};
+    final Object? message = data['message'];
+    if (message is Map<String, dynamic>) {
+      return message;
+    }
+    return <String, dynamic>{};
+  }
+
+  Future<String> _executeTool(
+    String toolName,
+    Map<String, dynamic> arguments,
+  ) async {
+    try {
+      switch (toolName) {
+        case 'search_web':
+          final String query = _stringValue(arguments['query']);
+          final int maxResults =
+              (arguments['maxResults'] as num?)?.toInt() ?? 5;
+          final List<OllamaWebSearchResult> results = await _webSearchClient
+              .search(query, maxResults: maxResults);
+          return jsonEncode(<String, dynamic>{
+            'query': query,
+            'results': results
+                .map((OllamaWebSearchResult result) => result.toJson())
+                .toList(growable: false),
+          });
+        case 'fetch_web_page':
+          final String url = _stringValue(arguments['url']);
+          final String text = await _webSearchClient.fetchPageText(url);
+          return jsonEncode(<String, String>{'url': url, 'text': text});
+        default:
+          return jsonEncode(<String, String>{
+            'error': 'Unknown tool: $toolName',
+          });
+      }
+    } catch (error) {
+      return jsonEncode(<String, String>{
+        'error': 'Tool $toolName failed: $error',
+      });
+    }
+  }
+}
+
+String _toolSystemPrompt(String systemPrompt) {
+  return '''
+$systemPrompt
+
+When you need current web information, call search_web first. Use fetch_web_page
+only for URLs returned by search_web or URLs present in the user input. After
+tool results are available, produce the final answer in the exact JSON schema
+requested above. Do not expose tool-call internals in the final answer.
+''';
+}
+
+List<Map<String, dynamic>> _toolCalls(Map<String, dynamic> message) {
+  final Object? toolCalls = message['tool_calls'];
+  if (toolCalls is! List<dynamic>) {
+    return const <Map<String, dynamic>>[];
+  }
+  return toolCalls
+      .whereType<Map<dynamic, dynamic>>()
+      .map(
+        (Map<dynamic, dynamic> item) =>
+            item.map((dynamic key, dynamic value) => MapEntry('$key', value)),
+      )
+      .toList(growable: false);
+}
+
+String _toolName(Map<String, dynamic> toolCall) {
+  final Object? function = toolCall['function'];
+  if (function is Map<String, dynamic>) {
+    return _stringValue(function['name']);
+  }
+  return _stringValue(toolCall['name']);
+}
+
+Map<String, dynamic> _toolArguments(Map<String, dynamic> toolCall) {
+  final Object? function = toolCall['function'];
+  final Object? rawArguments = function is Map<String, dynamic>
+      ? function['arguments']
+      : toolCall['arguments'];
+  if (rawArguments is Map<String, dynamic>) {
+    return rawArguments;
+  }
+  if (rawArguments is Map<dynamic, dynamic>) {
+    return rawArguments.map(
+      (dynamic key, dynamic value) => MapEntry('$key', value),
+    );
+  }
+  if (rawArguments is String && rawArguments.trim().isNotEmpty) {
+    final Object? decoded = jsonDecode(rawArguments);
+    if (decoded is Map<String, dynamic>) {
+      return decoded;
+    }
+    if (decoded is Map<dynamic, dynamic>) {
+      return decoded.map(
+        (dynamic key, dynamic value) => MapEntry('$key', value),
+      );
+    }
+  }
+  return const <String, dynamic>{};
+}
+
+String _stringValue(Object? value) {
+  if (value is String) {
+    return value.trim();
+  }
+  return '';
+}
+
+List<Map<String, dynamic>> get _tools {
+  return <Map<String, dynamic>>[
+    <String, dynamic>{
+      'type': 'function',
+      'function': <String, dynamic>{
+        'name': 'search_web',
+        'description':
+            'Search the public web for current event, venue, date, price, '
+            'availability, and source information.',
+        'parameters': <String, dynamic>{
+          'type': 'object',
+          'properties': <String, dynamic>{
+            'query': <String, dynamic>{
+              'type': 'string',
+              'description': 'Specific search query.',
+            },
+            'maxResults': <String, dynamic>{
+              'type': 'integer',
+              'description': 'Maximum number of search results to return.',
+              'minimum': 1,
+              'maximum': 10,
+            },
+          },
+          'required': <String>['query'],
+        },
+      },
+    },
+    <String, dynamic>{
+      'type': 'function',
+      'function': <String, dynamic>{
+        'name': 'fetch_web_page',
+        'description':
+            'Fetch readable text from a specific web page when the search '
+            'snippet is not enough to verify event details.',
+        'parameters': <String, dynamic>{
+          'type': 'object',
+          'properties': <String, dynamic>{
+            'url': <String, dynamic>{
+              'type': 'string',
+              'description': 'HTTP or HTTPS URL to fetch.',
+            },
+          },
+          'required': <String>['url'],
+        },
+      },
+    },
+  ];
+}
+
+Dio _createDio() {
+  return Dio(
+    BaseOptions(
+      connectTimeout: const Duration(seconds: 20),
+      receiveTimeout: const Duration(minutes: 5),
+      sendTimeout: const Duration(seconds: 20),
+    ),
+  );
+}
+
+final Provider<OllamaToolChatClient> ollamaToolChatClientProvider =
+    Provider<OllamaToolChatClient>((Ref ref) {
+      return OllamaToolChatClient(
+        webSearchClient: ref.watch(ollamaWebSearchClientProvider),
+      );
+    });
@@ -0,0 +1,173 @@
+import 'dart:convert';
+
+import 'package:dio/dio.dart';
+import 'package:flutter_riverpod/flutter_riverpod.dart';
+
+class OllamaWebSearchResult {
+  const OllamaWebSearchResult({
+    required this.title,
+    required this.url,
+    required this.snippet,
+  });
+
+  final String title;
+  final String url;
+  final String snippet;
+
+  Map<String, String> toJson() {
+    return <String, String>{'title': title, 'url': url, 'snippet': snippet};
+  }
+}
+
+abstract interface class OllamaWebSearchClient {
+  Future<List<OllamaWebSearchResult>> search(
+    String query, {
+    int maxResults = 5,
+  });
+
+  Future<String> fetchPageText(String url);
+}
+
+class DuckDuckGoOllamaWebSearchClient implements OllamaWebSearchClient {
+  DuckDuckGoOllamaWebSearchClient({Dio? dio}) : _dio = dio ?? _createDio();
+
+  final Dio _dio;
+
+  @override
+  Future<List<OllamaWebSearchResult>> search(
+    String query, {
+    int maxResults = 5,
+  }) async {
+    final String normalizedQuery = query.trim();
+    if (normalizedQuery.isEmpty) {
+      return const <OllamaWebSearchResult>[];
+    }
+
+    final Response<Map<String, dynamic>> response = await _dio
+        .get<Map<String, dynamic>>(
+          'https://api.duckduckgo.com/',
+          queryParameters: <String, Object>{
+            'q': normalizedQuery,
+            'format': 'json',
+            'no_html': 1,
+            'skip_disambig': 1,
+          },
+        );
+    final Map<String, dynamic> data = response.data ?? <String, dynamic>{};
+    final List<OllamaWebSearchResult> results = <OllamaWebSearchResult>[];
+
+    final String abstractUrl = _stringValue(data['AbstractURL']);
+    final String abstractText = _stringValue(data['AbstractText']);
+    final String heading = _stringValue(data['Heading']);
+    if (abstractUrl.isNotEmpty && abstractText.isNotEmpty) {
+      results.add(
+        OllamaWebSearchResult(
+          title: heading.isEmpty ? abstractUrl : heading,
+          url: abstractUrl,
+          snippet: abstractText,
+        ),
+      );
+    }
+
+    _collectRelatedTopics(data['Results'], results);
+    _collectRelatedTopics(data['RelatedTopics'], results);
+
+    final Set<String> seenUrls = <String>{};
+    return results
+        .where((OllamaWebSearchResult result) => seenUrls.add(result.url))
+        .take(maxResults.clamp(1, 10))
+        .toList(growable: false);
+  }
+
+  @override
+  Future<String> fetchPageText(String url) async {
+    final Uri? uri = Uri.tryParse(url.trim());
+    if (uri == null || !(uri.scheme == 'http' || uri.scheme == 'https')) {
+      return jsonEncode(<String, String>{'error': 'Invalid URL.'});
+    }
+
+    final Response<String> response = await _dio.get<String>(
+      uri.toString(),
+      options: Options(responseType: ResponseType.plain),
+    );
+    return _compactText(_htmlToText(response.data ?? ''));
+  }
+
+  static void _collectRelatedTopics(
+    Object? value,
+    List<OllamaWebSearchResult> results,
+  ) {
+    if (value is! List<dynamic>) {
+      return;
+    }
+    for (final Object? item in value) {
+      if (item is! Map<String, dynamic>) {
+        continue;
+      }
+      final Object? nestedTopics = item['Topics'];
+      if (nestedTopics is List<dynamic>) {
+        _collectRelatedTopics(nestedTopics, results);
+        continue;
+      }
+
+      final String firstUrl = _stringValue(item['FirstURL']);
+      final String text = _stringValue(item['Text']);
+      if (firstUrl.isEmpty || text.isEmpty) {
+        continue;
+      }
+      results.add(
+        OllamaWebSearchResult(
+          title: text.split(' - ').first.trim(),
+          url: firstUrl,
+          snippet: text,
+        ),
+      );
+    }
+  }
+}
+
+String _stringValue(Object? value) {
+  if (value is String) {
+    return value.trim();
+  }
+  return '';
+}
+
+String _htmlToText(String html) {
+  return html
+      .replaceAll(
+        RegExp(r'<script[\s\S]*?</script>', caseSensitive: false),
+        ' ',
+      )
+      .replaceAll(RegExp(r'<style[\s\S]*?</style>', caseSensitive: false), ' ')
+      .replaceAll(RegExp(r'<[^>]+>'), ' ')
+      .replaceAll('&nbsp;', ' ')
+      .replaceAll('&amp;', '&')
+      .replaceAll('&lt;', '<')
+      .replaceAll('&gt;', '>')
+      .replaceAll('&quot;', '"')
+      .replaceAll('&#39;', "'");
+}
+
+String _compactText(String value) {
+  final String compacted = value.trim().replaceAll(RegExp(r'\s+'), ' ');
+  if (compacted.length <= 4000) {
+    return compacted;
+  }
+  return '${compacted.substring(0, 3997)}...';
+}
+
+Dio _createDio() {
+  return Dio(
+    BaseOptions(
+      connectTimeout: const Duration(seconds: 20),
+      receiveTimeout: const Duration(seconds: 20),
+      sendTimeout: const Duration(seconds: 20),
+    ),
+  );
+}
+
+final Provider<OllamaWebSearchClient> ollamaWebSearchClientProvider =
+    Provider<OllamaWebSearchClient>((Ref ref) {
+      return DuckDuckGoOllamaWebSearchClient();
+    });
@@ -28,7 +28,7 @@ class SentryInit {
  Future<void> _initializeInternal({
    FutureOr<void> Function()? appRunner,
  }) async {
-    if (!kReleaseMode || AppConfig.sentryDsn.isEmpty) {
+    if (AppConfig.sentryDsn.isEmpty) {
      if (appRunner != null) {
        await Future<void>.sync(appRunner);
      }
@@ -37,25 +37,90 @@ class SentryInit {

    await SentryFlutter.init((options) {
      options.dsn = AppConfig.sentryDsn;
-      options.environment = AppConfig.useFakeBackend
-          ? 'development'
-          : 'production';
+      options.environment = AppConfig.sentryEnvironment;
+      options.release = AppConfig.sentryRelease;
+      options.sendDefaultPii = false;
      options.tracesSampleRate = 0.1;
    }, appRunner: appRunner);
+    await Sentry.configureScope((scope) async {
+      await scope.setTag('service', 'relationship_saver');
+      await scope.setTag('build_mode', kReleaseMode ? 'release' : 'debug');
+    });
+    _installGlobalHandlers();
    _initialized = true;
  }

-  void captureException(Object error, {StackTrace? stackTrace}) {
+  void captureException(
+    Object error, {
+    StackTrace? stackTrace,
+    String? area,
+    Map<String, dynamic>? context,
+  }) {
    if (_initialized) {
-      Sentry.captureException(error, stackTrace: stackTrace);
+      unawaited(
+        Sentry.captureException(
+          error,
+          stackTrace: stackTrace,
+          withScope: (scope) async {
+            if (area != null) {
+              await scope.setTag('area', area);
+            }
+            if (context != null) {
+              await scope.setContexts('diagnostics', context);
+            }
+          },
+        ),
+      );
    }
  }

-  void captureMessage(String message, {SentryLevel level = SentryLevel.info}) {
+  void captureMessage(
+    String message, {
+    SentryLevel level = SentryLevel.info,
+    String? area,
+    Map<String, dynamic>? context,
+  }) {
    if (_initialized) {
-      Sentry.captureMessage(message, level: level);
+      unawaited(
+        Sentry.captureMessage(
+          message,
+          level: level,
+          withScope: (scope) async {
+            if (area != null) {
+              await scope.setTag('area', area);
+            }
+            if (context != null) {
+              await scope.setContexts('diagnostics', context);
+            }
+          },
+        ),
+      );
    }
  }
+
+  void _installGlobalHandlers() {
+    final FlutterExceptionHandler? previousFlutterHandler =
+        FlutterError.onError;
+    FlutterError.onError = (FlutterErrorDetails details) {
+      previousFlutterHandler?.call(details);
+      captureException(
+        details.exception,
+        stackTrace: details.stack,
+        area: 'flutter_framework',
+        context: <String, dynamic>{
+          'library': details.library,
+          'context': details.context?.toDescription(),
+        },
+      );
+    };
+
+    final ErrorCallback? previousPlatformHandler =
+        PlatformDispatcher.instance.onError;
+    PlatformDispatcher.instance.onError = (Object error, StackTrace stack) {
+      captureException(error, stackTrace: stack, area: 'platform_dispatcher');
+      return previousPlatformHandler?.call(error, stack) ?? false;
+    };
+  }
 }

 final sentryInitProvider = Provider<SentryInit>((Ref ref) {
@@ -69,6 +69,16 @@ class AiDigestResponseParser {
            suggestedFor:
                _dateOrNull(item['suggestedFor']) ??
                _dateOrNull(item['suggestedTiming']),
+            eventEndsAt:
+                _dateOrNull(item['eventEndsAt']) ??
+                _dateOrNull(item['endsAt']) ??
+                _dateOrNull(item['endTime']),
+            eventLocation: _optionalTrimAndCap(
+              _string(item['eventLocation']) ?? _string(item['location']),
+              160,
+            ),
+            eventUrl: _urlOrNull(item['eventUrl']) ?? _urlOrNull(item['url']),
+            sourceUrls: _sourceUrls(item['sourceUrls'] ?? item['sources']),
            confidence: _confidence(item['confidence']),
            status: AiSuggestionStatus.pending,
            sourceRunId: sourceRunId,
@@ -158,6 +168,40 @@ class AiDigestResponseParser {
    return DateTime.tryParse(value)?.toLocal();
  }

+  String? _urlOrNull(Object? raw) {
+    final String? value = _string(raw);
+    if (value == null) {
+      return null;
+    }
+    final Uri? uri = Uri.tryParse(value);
+    if (uri == null || !uri.hasScheme || uri.host.isEmpty) {
+      return null;
+    }
+    return uri.toString();
+  }
+
+  List<String> _sourceUrls(Object? raw) {
+    final List<Object?> values = raw is List<dynamic> ? raw : <Object?>[raw];
+    final Set<String> urls = <String>{};
+    for (final Object? value in values) {
+      if (value is Map<String, dynamic>) {
+        final String? url =
+            _urlOrNull(value['url']) ??
+            _urlOrNull(value['uri']) ??
+            _urlOrNull(value['link']);
+        if (url != null) {
+          urls.add(url);
+        }
+        continue;
+      }
+      final String? url = _urlOrNull(value);
+      if (url != null) {
+        urls.add(url);
+      }
+    }
+    return urls.take(5).toList(growable: false);
+  }
+
  double _confidence(Object? raw) {
    if (raw is num) {
      return raw.toDouble().clamp(0.0, 1.0).toDouble();
@@ -172,4 +216,12 @@ class AiDigestResponseParser {
    }
    return trimmed.substring(0, maxChars).trim();
  }
+
+  String? _optionalTrimAndCap(String? value, int maxChars) {
+    if (value == null) {
+      return null;
+    }
+    final String trimmed = _trimAndCap(value, maxChars);
+    return trimmed.isEmpty ? null : trimmed;
+  }
 }
@@ -4,6 +4,7 @@ import 'dart:math' as math;
 import 'package:relationship_saver/app/state/local_data_state.dart';
 import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
 import 'package:relationship_saver/features/people/domain/person_models.dart';
+import 'package:relationship_saver/features/share_intake/domain/share_models.dart';

 class AnonymizedLlmDigestContext {
  const AnonymizedLlmDigestContext({
@@ -23,12 +24,14 @@ class AnonymizedLlmContextBuilder {
  const AnonymizedLlmContextBuilder({
    this.maxPeople = 20,
    this.maxSignalsPerPerson = 8,
+    this.maxFactsPerPerson = 8,
    this.maxPriorSuggestionsPerPerson = 6,
    DateTime Function()? now,
  }) : _now = now ?? DateTime.now;

  final int maxPeople;
  final int maxSignalsPerPerson;
+  final int maxFactsPerPerson;
  final int maxPriorSuggestionsPerPerson;
  final DateTime Function() _now;

@@ -69,7 +72,11 @@ class AnonymizedLlmContextBuilder {
          'Do not infer or ask for names.',
          'Return JSON only.',
          'Prefer practical suggestions that can be reviewed before saving.',
+          'Use web search for current event recommendations and include source URLs.',
+          'Only suggest real upcoming events with verified date and venue details.',
          'Do not repeat priorSuggestions for the same personToken.',
+          'When shared_message_datetime is present, treat it as the point-in-time reference for that evidence.',
+          'Do not turn old health/status evidence into a current check-in; preserve durable preferences instead.',
        ],
        'limits': <String, dynamic>{
          'maxItems': 10,
@@ -188,10 +195,81 @@ class AnonymizedLlmContextBuilder {
            .map((PersonPreferenceSignal signal) => 'avoid ${signal.label}')
            .toList(growable: false),
      ).take(maxSignalsPerPerson).toList(growable: false),
+      'preferenceSignals': _preferenceSignals(signals, now),
+      'capturedFacts': _capturedFacts(state, person, now),
      'priorSuggestions': _priorSuggestions(state, person),
    };
  }

+  List<Map<String, String>> _capturedFacts(
+    LocalDataState state,
+    PersonProfile person,
+    DateTime now,
+  ) {
+    final List<String> identityTerms = _identityTerms(state);
+    final Map<String, DateTime> sharedMessageTimes = _sharedMessageTimes(state);
+    return state.personFacts
+        .where(
+          (PersonFact fact) =>
+              fact.personId == person.id &&
+              !fact.isSensitive &&
+              !fact.needsReview &&
+              fact.text.trim().isNotEmpty,
+        )
+        .take(maxFactsPerPerson)
+        .map((PersonFact fact) {
+          final DateTime? sharedMessageDateTime = fact.sharedMessageId == null
+              ? null
+              : sharedMessageTimes[fact.sharedMessageId];
+          return <String, String>{
+            'type': _factTypeLabel(fact.type),
+            if (_safeContextText(fact.label, identityTerms).isNotEmpty)
+              'label': _safeContextText(fact.label, identityTerms),
+            'summary': _safeContextText(fact.text, identityTerms),
+            if (sharedMessageDateTime != null) ...<String, String>{
+              'shared_message_datetime': sharedMessageDateTime
+                  .toUtc()
+                  .toIso8601String(),
+              'sourceAge': _ageLabel(sharedMessageDateTime, now),
+            },
+          };
+        })
+        .where(
+          (Map<String, String> fact) =>
+              fact['summary'] != null && fact['summary']!.isNotEmpty,
+        )
+        .toList(growable: false);
+  }
+
+  List<Map<String, String>> _preferenceSignals(
+    List<PersonPreferenceSignal> signals,
+    DateTime now,
+  ) {
+    return signals
+        .map(
+          (PersonPreferenceSignal signal) => <String, String>{
+            'label': _safeCategory(signal.label),
+            'category': _safeCategory(signal.category),
+            'polarity': signal.polarity == PreferenceSignalPolarity.dislike
+                ? 'dislike'
+                : 'like',
+            'lastObserved': signal.lastSeenAt.toUtc().toIso8601String(),
+            'sourceAge': _ageLabel(signal.lastSeenAt, now),
+          },
+        )
+        .where((Map<String, String> signal) => signal['label']!.isNotEmpty)
+        .take(maxSignalsPerPerson)
+        .toList(growable: false);
+  }
+
+  Map<String, DateTime> _sharedMessageTimes(LocalDataState state) {
+    return <String, DateTime>{
+      for (final SharedMessageEntry entry in state.sharedMessages)
+        if (entry.sharedMessageDateTime != null)
+          entry.id: entry.sharedMessageDateTime!,
+    };
+  }
+
  List<Map<String, String>> _priorSuggestions(
    LocalDataState state,
    PersonProfile person,
@@ -272,6 +350,18 @@ class AnonymizedLlmContextBuilder {
    return 'last contact about $days days ago';
  }

+  String _ageLabel(DateTime value, DateTime now) {
+    final int days = now.difference(value).inDays;
+    if (days <= 1) {
+      return 'current or recent';
+    }
+    if (days < 45) {
+      return 'about $days days ago';
+    }
+    final int months = (days / 30).round().clamp(2, 24).toInt();
+    return 'about $months months ago';
+  }
+
  List<String> _safeList(Iterable<String> values) {
    final List<String> out = <String>[];
    final Set<String> seen = <String>{};
@@ -297,6 +387,58 @@ class AnonymizedLlmContextBuilder {
        .toLowerCase();
  }

+  String _safeContextText(String? value, List<String> identityTerms) {
+    if (value == null) {
+      return '';
+    }
+    String safe = value.trim().replaceAll(RegExp(r'https?://\S+'), '');
+    for (final String term in identityTerms) {
+      safe = safe.replaceAll(
+        RegExp(RegExp.escape(term), caseSensitive: false),
+        'this person',
+      );
+    }
+    return safe
+        .replaceAll(RegExp(r'[\r\n\t]+'), ' ')
+        .replaceAll(RegExp(r'[^a-zA-Z0-9 .,;:!?+&%$#@()\-/]+'), '')
+        .replaceAll(RegExp(r'\s+'), ' ')
+        .trim()
+        .toLowerCase();
+  }
+
+  List<String> _identityTerms(LocalDataState state) {
+    final Set<String> terms = <String>{};
+    for (final PersonProfile person in state.people) {
+      for (final String raw in <String>[person.name, ...person.aliases]) {
+        final String term = raw.trim();
+        if (term.length >= 3) {
+          terms.add(term);
+        }
+        for (final String part in term.split(RegExp(r'\s+'))) {
+          if (part.length >= 3) {
+            terms.add(part);
+          }
+        }
+      }
+    }
+    final List<String> sorted = terms.toList(growable: false)
+      ..sort((String a, String b) => b.length.compareTo(a.length));
+    return sorted;
+  }
+
+  String _factTypeLabel(CapturedFactType type) {
+    return switch (type) {
+      CapturedFactType.note => 'note',
+      CapturedFactType.like => 'like',
+      CapturedFactType.dislike => 'dislike',
+      CapturedFactType.importantDate => 'important date',
+      CapturedFactType.giftIdea => 'gift idea',
+      CapturedFactType.placeIdea => 'place idea',
+      CapturedFactType.activityIdea => 'activity idea',
+      CapturedFactType.misc => 'misc',
+    };
+  }
+
  int _daysUntil(DateTime date, DateTime now) {
    return date.difference(DateTime(now.year, now.month, now.day)).inDays;
  }
@@ -0,0 +1,53 @@
+import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
+import 'package:url_launcher/url_launcher.dart';
+
+class CalendarEventLauncher {
+  const CalendarEventLauncher();
+
+  Future<bool> addSuggestionToCalendar(AiSuggestionDraft draft) async {
+    final Uri? uri = calendarUriForSuggestion(draft);
+    if (uri == null) {
+      return false;
+    }
+    if (await launchUrl(uri, mode: LaunchMode.externalApplication)) {
+      return true;
+    }
+    return launchUrl(uri);
+  }
+}
+
+Uri? calendarUriForSuggestion(AiSuggestionDraft draft) {
+  final DateTime? startsAt = draft.suggestedFor;
+  if (draft.kind != AiSuggestionKind.eventIdea || startsAt == null) {
+    return null;
+  }
+  final DateTime endsAt =
+      draft.eventEndsAt ?? startsAt.add(const Duration(hours: 2));
+  final String details = <String>[
+    draft.details,
+    if (draft.reason != null && draft.reason!.trim().isNotEmpty)
+      'Why: ${draft.reason!.trim()}',
+    if (draft.eventUrl != null && draft.eventUrl!.trim().isNotEmpty)
+      draft.eventUrl!.trim(),
+    if (draft.sourceUrls.isNotEmpty) 'Sources: ${draft.sourceUrls.join(', ')}',
+  ].where((String value) => value.trim().isNotEmpty).join('\n\n');
+
+  return Uri.https('calendar.google.com', '/calendar/render', <String, String>{
+    'action': 'TEMPLATE',
+    'text': draft.title,
+    'dates': '${_calendarTimestamp(startsAt)}/${_calendarTimestamp(endsAt)}',
+    if (details.isNotEmpty) 'details': details,
+    if (draft.eventLocation != null && draft.eventLocation!.trim().isNotEmpty)
+      'location': draft.eventLocation!.trim(),
+  });
+}
+
+String _calendarTimestamp(DateTime value) {
+  final DateTime utc = value.toUtc();
+  return '${utc.year.toString().padLeft(4, '0')}'
+      '${utc.month.toString().padLeft(2, '0')}'
+      '${utc.day.toString().padLeft(2, '0')}T'
+      '${utc.hour.toString().padLeft(2, '0')}'
+      '${utc.minute.toString().padLeft(2, '0')}'
+      '${utc.second.toString().padLeft(2, '0')}Z';
+}
@@ -3,6 +3,7 @@ import 'package:relationship_saver/app/data/relationship_repository.dart';
 import 'package:relationship_saver/app/state/local_data_state.dart';
 import 'package:relationship_saver/core/llm/llm_config.dart';
 import 'package:relationship_saver/core/llm/llm_service.dart';
+import 'package:relationship_saver/core/observability/sentry_init.dart';
 import 'package:relationship_saver/features/ai_digest/application/ai_digest_notifier.dart';
 import 'package:relationship_saver/features/ai_digest/application/ai_digest_response_parser.dart';
 import 'package:relationship_saver/features/ai_digest/application/anonymized_llm_context_builder.dart';
@@ -11,6 +12,7 @@ import 'package:relationship_saver/features/ai_digest/application/llm_digest_tex
 import 'package:relationship_saver/features/ai_digest/data/llm_digest_config.dart';
 import 'package:relationship_saver/features/ai_digest/data/llm_digest_run_store.dart';
 import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
+import 'package:sentry_flutter/sentry_flutter.dart';
 import 'package:uuid/uuid.dart';

 const Duration _scheduledCooldown = Duration(days: 7);
@@ -107,7 +109,8 @@ class LlmDigestOrchestrator {
      );
    }

-    if (!await _ref.read(llmDigestEnvironmentProvider).canRun(config)) {
+    if (!bypassCooldown &&
+        !await _ref.read(llmDigestEnvironmentProvider).canRun(config)) {
      return const LlmDigestRunResult(
        started: false,
        completed: false,
@@ -143,12 +146,11 @@ class LlmDigestOrchestrator {
      }

      final String sourceRunId = 'digest-${_uuid.v4()}';
-      final String response = await _ref
-          .read(llmDigestTextClientProvider)
-          .complete(
-            systemPrompt: _systemPrompt,
-            userPrompt: context.toPromptJson(),
-          );
+      final String response = await _completeDigestPrompt(
+        userPrompt: context.toPromptJson(),
+        enableWebSearch: config.enableWebSearch,
+        sourceRunId: sourceRunId,
+      );
      final AiDigestParseResult parsed = const AiDigestResponseParser().parse(
        response: response,
        tokenToPersonId: context.tokenToPersonId,
@@ -157,6 +159,18 @@ class LlmDigestOrchestrator {
      );

      if (!parsed.success) {
+        _ref
+            .read(sentryInitProvider)
+            .captureMessage(
+              parsed.error ?? 'Invalid digest response.',
+              level: SentryLevel.warning,
+              area: 'llm_digest_parse',
+              context: <String, dynamic>{
+                'sourceRunId': sourceRunId,
+                'responseChars': response.length,
+                'eligiblePeople': context.tokenToPersonId.length,
+              },
+            );
        await _markFailure(parsed.error ?? 'Invalid digest response.');
        return LlmDigestRunResult(
          started: true,
@@ -185,8 +199,19 @@ class LlmDigestOrchestrator {
        completed: true,
        createdDraftCount: parsed.drafts.length,
      );
-    } catch (error) {
+    } catch (error, stackTrace) {
      final String reason = _digestFailureReason(error);
+      _ref
+          .read(sentryInitProvider)
+          .captureException(
+            error,
+            stackTrace: stackTrace,
+            area: 'llm_digest',
+            context: <String, dynamic>{
+              'bypassCooldown': bypassCooldown,
+              'notify': notify,
+            },
+          );
      await _markFailure(reason);
      return LlmDigestRunResult(
        started: true,
@@ -196,6 +221,45 @@ class LlmDigestOrchestrator {
    }
  }

+  Future<String> _completeDigestPrompt({
+    required String userPrompt,
+    required bool enableWebSearch,
+    required String sourceRunId,
+  }) async {
+    try {
+      return await _ref
+          .read(llmDigestTextClientProvider)
+          .complete(
+            systemPrompt: _systemPrompt(enableWebSearch: enableWebSearch),
+            userPrompt: userPrompt,
+            enableWebSearch: enableWebSearch,
+          );
+    } on LlmProviderException catch (error) {
+      if (!enableWebSearch || error.statusCode != 429) {
+        rethrow;
+      }
+      _ref
+          .read(sentryInitProvider)
+          .captureMessage(
+            'Grounded digest request hit provider quota; retrying without web search.',
+            level: SentryLevel.warning,
+            area: 'llm_digest_grounding_fallback',
+            context: <String, dynamic>{
+              'sourceRunId': sourceRunId,
+              'provider': error.provider.name,
+              'statusCode': error.statusCode,
+            },
+          );
+      return _ref
+          .read(llmDigestTextClientProvider)
+          .complete(
+            systemPrompt: _systemPrompt(enableWebSearch: false),
+            userPrompt: userPrompt,
+            enableWebSearch: false,
+          );
+    }
+  }
+
  Future<void> _markFailure(String reason) async {
    final LlmDigestRunStore store = _ref.read(llmDigestRunStoreProvider);
    final LlmDigestRunState current = await store.read();
@@ -241,7 +305,21 @@ String _digestFailureReason(Object error) {
  return '$error';
 }

-const String _systemPrompt = '''
+String _systemPrompt({required bool enableWebSearch}) {
+  final String groundingRules = enableWebSearch
+      ? '''
+Use web search for current event, venue, availability, price, and timing claims.
+Prefer official event or venue pages over aggregators. Only classify an item as
+eventIdea when there is a real upcoming event with a concrete date in the next
+60 days. Include sourceUrls for grounded suggestions and do not fabricate URLs.
+'''
+      : '''
+Web search grounding is disabled or unavailable for this run. Do not make
+current availability, price, or venue claims. Avoid eventIdea suggestions unless
+the input already contains enough concrete event details and leave sourceUrls
+empty when no source URL was provided.
+''';
+  return '''
 You create private relationship-maintenance digest suggestions.
 The input contains pseudonymous people only. Never ask for or invent names.
 Return exactly one JSON object:
@@ -252,14 +330,24 @@ Return exactly one JSON object:
      "kind": "giftIdea" | "eventIdea" | "checkIn" | "reminder",
      "title": "short action title",
      "details": "practical details for the user to review",
-      "suggestedTiming": "optional ISO-8601 date or null",
+      "suggestedTiming": "optional ISO-8601 start date/time or null",
+      "eventEndsAt": "optional ISO-8601 end date/time for eventIdea only, otherwise null",
+      "eventLocation": "optional venue or city for eventIdea only, otherwise null",
+      "eventUrl": "optional official event URL for eventIdea only, otherwise null",
+      "sourceUrls": ["0-3 source URLs used to verify the suggestion"],
      "confidence": 0.0,
      "reason": "brief non-sensitive rationale"
    }
  ]
 }
 Return at most 10 suggestions. Use only personToken values present in input.
+If an input fact includes shared_message_datetime, use that timestamp as the
+evidence date. A message from months ago about temporary health, travel, mood,
+or availability should not produce an immediate checkIn unless other recent
+evidence supports it; keep durable preferences, constraints, and gift ideas.
+$groundingRules
 ''';
+}

 final Provider<LlmDigestOrchestrator> llmDigestOrchestratorProvider =
    Provider<LlmDigestOrchestrator>((Ref ref) => LlmDigestOrchestrator(ref));
@@ -5,6 +5,7 @@ abstract interface class LlmDigestTextClient {
  Future<String> complete({
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  });
 }

@@ -17,10 +18,12 @@ class ConfiguredLlmDigestTextClient implements LlmDigestTextClient {
  Future<String> complete({
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  }) {
    return _service.completeText(
      systemPrompt: systemPrompt,
      userPrompt: userPrompt,
+      enableWebSearch: enableWebSearch,
    );
  }
 }
@@ -7,6 +7,7 @@ const String _preferredWeekdayKey = 'llm_digest_preferred_weekday';
 const String _preferredHourKey = 'llm_digest_preferred_hour';
 const String _requireWifiKey = 'llm_digest_require_wifi';
 const String _requireChargingKey = 'llm_digest_require_charging';
+const String _enableWebSearchKey = 'llm_digest_enable_web_search';

 class LlmDigestConfigNotifier extends Notifier<LlmDigestConfigState> {
  Future<void>? _initializeFuture;
@@ -29,6 +30,7 @@ class LlmDigestConfigNotifier extends Notifier<LlmDigestConfigState> {
      preferredHour: prefs.getInt(_preferredHourKey) ?? 21,
      requireWifi: prefs.getBool(_requireWifiKey) ?? true,
      requireCharging: prefs.getBool(_requireChargingKey) ?? true,
+      enableWebSearch: prefs.getBool(_enableWebSearchKey) ?? true,
    );
  }

@@ -68,6 +70,12 @@ class LlmDigestConfigNotifier extends Notifier<LlmDigestConfigState> {
      requireCharging: requireCharging,
    );
  }
+
+  Future<void> setWebSearchEnabled(bool enabled) async {
+    final SharedPreferences prefs = await SharedPreferences.getInstance();
+    await prefs.setBool(_enableWebSearchKey, enabled);
+    state = state.copyWith(enableWebSearch: enabled);
+  }
 }

 final NotifierProvider<LlmDigestConfigNotifier, LlmDigestConfigState>
@@ -21,6 +21,10 @@ class AiSuggestionDraft {
    required this.status,
    required this.sourceRunId,
    this.suggestedFor,
+    this.eventEndsAt,
+    this.eventLocation,
+    this.eventUrl,
+    this.sourceUrls = const <String>[],
    this.reason,
  });

@@ -31,6 +35,10 @@ class AiSuggestionDraft {
  final String details;
  final DateTime suggestedAt;
  final DateTime? suggestedFor;
+  final DateTime? eventEndsAt;
+  final String? eventLocation;
+  final String? eventUrl;
+  final List<String> sourceUrls;
  final double confidence;
  final AiSuggestionStatus status;
  final String sourceRunId;
@@ -44,6 +52,10 @@ class AiSuggestionDraft {
    String? details,
    DateTime? suggestedAt,
    DateTime? suggestedFor,
+    DateTime? eventEndsAt,
+    String? eventLocation,
+    String? eventUrl,
+    List<String>? sourceUrls,
    double? confidence,
    AiSuggestionStatus? status,
    String? sourceRunId,
@@ -57,6 +69,10 @@ class AiSuggestionDraft {
      details: details ?? this.details,
      suggestedAt: suggestedAt ?? this.suggestedAt,
      suggestedFor: suggestedFor ?? this.suggestedFor,
+      eventEndsAt: eventEndsAt ?? this.eventEndsAt,
+      eventLocation: eventLocation ?? this.eventLocation,
+      eventUrl: eventUrl ?? this.eventUrl,
+      sourceUrls: sourceUrls ?? this.sourceUrls,
      confidence: confidence ?? this.confidence,
      status: status ?? this.status,
      sourceRunId: sourceRunId ?? this.sourceRunId,
@@ -73,6 +89,10 @@ class AiSuggestionDraft {
      'details': details,
      'suggestedAt': suggestedAt.toUtc().toIso8601String(),
      'suggestedFor': suggestedFor?.toUtc().toIso8601String(),
+      'eventEndsAt': eventEndsAt?.toUtc().toIso8601String(),
+      'eventLocation': eventLocation,
+      'eventUrl': eventUrl,
+      'sourceUrls': sourceUrls,
      'confidence': confidence,
      'status': status.name,
      'sourceRunId': sourceRunId,
@@ -101,6 +121,14 @@ class AiSuggestionDraft {
      suggestedFor: json['suggestedFor'] == null
          ? null
          : DateTime.parse(json['suggestedFor'] as String).toLocal(),
+      eventEndsAt: json['eventEndsAt'] == null
+          ? null
+          : DateTime.parse(json['eventEndsAt'] as String).toLocal(),
+      eventLocation: json['eventLocation'] as String?,
+      eventUrl: json['eventUrl'] as String?,
+      sourceUrls: (json['sourceUrls'] as List<dynamic>? ?? <dynamic>[])
+          .map((dynamic value) => '$value')
+          .toList(growable: false),
      confidence: (json['confidence'] as num?)?.toDouble() ?? 0,
      status: AiSuggestionStatus.values.firstWhere(
        (AiSuggestionStatus value) => value.name == statusName,
@@ -178,6 +206,7 @@ class LlmDigestConfigState {
    this.preferredHour = 21,
    this.requireWifi = true,
    this.requireCharging = true,
+    this.enableWebSearch = true,
  });

  final bool enabled;
@@ -186,6 +215,7 @@ class LlmDigestConfigState {
  final int preferredHour;
  final bool requireWifi;
  final bool requireCharging;
+  final bool enableWebSearch;

  LlmDigestConfigState copyWith({
    bool? enabled,
@@ -194,6 +224,7 @@ class LlmDigestConfigState {
    int? preferredHour,
    bool? requireWifi,
    bool? requireCharging,
+    bool? enableWebSearch,
  }) {
    return LlmDigestConfigState(
      enabled: enabled ?? this.enabled,
@@ -202,6 +233,7 @@ class LlmDigestConfigState {
      preferredHour: preferredHour ?? this.preferredHour,
      requireWifi: requireWifi ?? this.requireWifi,
      requireCharging: requireCharging ?? this.requireCharging,
+      enableWebSearch: enableWebSearch ?? this.enableWebSearch,
    );
  }
 }
@@ -3,6 +3,7 @@ import 'package:flutter_riverpod/flutter_riverpod.dart';
 import 'package:relationship_saver/app/data/relationship_repository.dart';
 import 'package:relationship_saver/app/state/local_data_state.dart';
 import 'package:relationship_saver/core/config/app_theme.dart';
+import 'package:relationship_saver/features/ai_digest/application/calendar_event_launcher.dart';
 import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
 import 'package:relationship_saver/features/people/domain/person_models.dart';
 import 'package:relationship_saver/features/shared/frosted_card.dart';
@@ -165,6 +166,13 @@ class _AiSuggestionCard extends StatelessWidget {
                icon: const Icon(Icons.check_rounded),
                label: const Text('Accept'),
              ),
+              if (draft.kind == AiSuggestionKind.eventIdea &&
+                  draft.suggestedFor != null)
+                OutlinedButton.icon(
+                  onPressed: () => _addToCalendar(context),
+                  icon: const Icon(Icons.calendar_month_rounded),
+                  label: const Text('Calendar'),
+                ),
              OutlinedButton.icon(
                onPressed: onDismiss,
                icon: const Icon(Icons.close_rounded),
@@ -177,6 +185,17 @@ class _AiSuggestionCard extends StatelessWidget {
    );
  }

+  Future<void> _addToCalendar(BuildContext context) async {
+    final bool launched = await const CalendarEventLauncher()
+        .addSuggestionToCalendar(draft);
+    if (!context.mounted || launched) {
+      return;
+    }
+    ScaffoldMessenger.of(
+      context,
+    ).showSnackBar(const SnackBar(content: Text('Could not open calendar.')));
+  }
+
  IconData _iconForKind(AiSuggestionKind kind) {
    return switch (kind) {
      AiSuggestionKind.giftIdea => Icons.card_giftcard_rounded,
@@ -3,6 +3,7 @@ import 'dart:math' as math;
 import 'package:flutter/material.dart';
 import 'package:flutter_riverpod/flutter_riverpod.dart';
 import 'package:relationship_saver/core/config/app_theme.dart';
+import 'package:relationship_saver/features/ai_digest/application/calendar_event_launcher.dart';
 import 'package:relationship_saver/features/local/local_models.dart';
 import 'package:relationship_saver/features/local/local_repository.dart';
 import 'package:relationship_saver/features/shared/frosted_card.dart';
@@ -22,6 +23,12 @@ class DashboardView extends ConsumerWidget {
      data: (LocalDataState data) {
        final DashboardSummary summary = data.summary();
        final List<DashboardTask> tasks = data.tasks;
+        final DateTime now = DateTime.now();
+        final List<AiSuggestionDraft> upcomingEventSuggestions =
+            _upcomingEventSuggestions(data.aiSuggestionDrafts, now);
+        final Map<String, PersonProfile> peopleById = <String, PersonProfile>{
+          for (final PersonProfile person in data.people) person.id: person,
+        };

        return LayoutBuilder(
          builder: (BuildContext context, BoxConstraints constraints) {
@@ -42,12 +49,19 @@ class DashboardView extends ConsumerWidget {
                  ),
                  const SizedBox(height: 8),
                  Text(
-                    'See the relationship graph first, then execute the highest-leverage next moves.',
+                    'Review incoming context, then act on time-sensitive opportunities.',
                    style: Theme.of(context).textTheme.bodyLarge?.copyWith(
                      color: AppTheme.textSecondary,
                    ),
                  ),
                  const SizedBox(height: 18),
+                  _HomeQueueCard(
+                    unresolvedShares: data.sharedInbox,
+                    upcomingEvents: upcomingEventSuggestions,
+                    peopleById: peopleById,
+                    compact: compact,
+                  ),
+                  const SizedBox(height: 20),
                  _RelationshipGraphCard(people: data.people, compact: compact),
                  const SizedBox(height: 20),
                  Wrap(
@@ -130,6 +144,293 @@ class DashboardView extends ConsumerWidget {
  }
 }

+class _HomeQueueCard extends StatelessWidget {
+  const _HomeQueueCard({
+    required this.unresolvedShares,
+    required this.upcomingEvents,
+    required this.peopleById,
+    required this.compact,
+  });
+
+  final List<SharedInboxEntry> unresolvedShares;
+  final List<AiSuggestionDraft> upcomingEvents;
+  final Map<String, PersonProfile> peopleById;
+  final bool compact;
+
+  @override
+  Widget build(BuildContext context) {
+    final List<Widget> sections = <Widget>[
+      _UnresolvedSharesPanel(entries: unresolvedShares),
+      _UpcomingEventsPanel(events: upcomingEvents, peopleById: peopleById),
+    ];
+    return compact
+        ? Column(
+            children: sections
+                .map(
+                  (Widget child) => Padding(
+                    padding: const EdgeInsets.only(bottom: 12),
+                    child: child,
+                  ),
+                )
+                .toList(growable: false),
+          )
+        : Row(
+            crossAxisAlignment: CrossAxisAlignment.start,
+            children: <Widget>[
+              Expanded(child: sections[0]),
+              const SizedBox(width: 14),
+              Expanded(child: sections[1]),
+            ],
+          );
+  }
+}
+
+class _UnresolvedSharesPanel extends StatelessWidget {
+  const _UnresolvedSharesPanel({required this.entries});
+
+  final List<SharedInboxEntry> entries;
+
+  @override
+  Widget build(BuildContext context) {
+    final List<SharedInboxEntry> visibleEntries = entries
+        .take(3)
+        .toList(growable: false);
+    return FrostedCard(
+      child: Column(
+        crossAxisAlignment: CrossAxisAlignment.start,
+        children: <Widget>[
+          Row(
+            children: <Widget>[
+              const Icon(Icons.inbox_rounded, color: AppTheme.primary),
+              const SizedBox(width: 10),
+              Expanded(
+                child: Text(
+                  'Unresolved Shares',
+                  style: Theme.of(context).textTheme.titleLarge,
+                ),
+              ),
+              _CountPill(count: entries.length),
+            ],
+          ),
+          const SizedBox(height: 12),
+          if (entries.isEmpty)
+            Text(
+              'Inbox is clear.',
+              style: Theme.of(
+                context,
+              ).textTheme.bodyMedium?.copyWith(color: AppTheme.textSecondary),
+            )
+          else
+            ...visibleEntries.map(
+              (SharedInboxEntry entry) => _ShareInboxPreview(entry: entry),
+            ),
+          if (entries.length > visibleEntries.length)
+            Text(
+              '+${entries.length - visibleEntries.length} more in inbox',
+              style: Theme.of(
+                context,
+              ).textTheme.labelLarge?.copyWith(color: AppTheme.textSecondary),
+            ),
+        ],
+      ),
+    );
+  }
+}
+
+class _ShareInboxPreview extends StatelessWidget {
+  const _ShareInboxPreview({required this.entry});
+
+  final SharedInboxEntry entry;
+
+  @override
+  Widget build(BuildContext context) {
+    final String sender = entry.sourceDisplayName?.trim().isNotEmpty == true
+        ? entry.sourceDisplayName!.trim()
+        : entry.sourceApp;
+    return Padding(
+      padding: const EdgeInsets.only(bottom: 10),
+      child: Row(
+        crossAxisAlignment: CrossAxisAlignment.start,
+        children: <Widget>[
+          const Icon(Icons.circle, size: 8, color: Color(0xFFFFA447)),
+          const SizedBox(width: 10),
+          Expanded(
+            child: Column(
+              crossAxisAlignment: CrossAxisAlignment.start,
+              children: <Widget>[
+                Text(
+                  sender,
+                  maxLines: 1,
+                  overflow: TextOverflow.ellipsis,
+                  style: Theme.of(context).textTheme.titleSmall,
+                ),
+                const SizedBox(height: 2),
+                Text(
+                  _compactShareText(entry.payload.rawText),
+                  maxLines: 2,
+                  overflow: TextOverflow.ellipsis,
+                  style: Theme.of(context).textTheme.bodyMedium?.copyWith(
+                    color: AppTheme.textSecondary,
+                  ),
+                ),
+              ],
+            ),
+          ),
+        ],
+      ),
+    );
+  }
+}
+
+class _UpcomingEventsPanel extends StatelessWidget {
+  const _UpcomingEventsPanel({required this.events, required this.peopleById});
+
+  final List<AiSuggestionDraft> events;
+  final Map<String, PersonProfile> peopleById;
+
+  @override
+  Widget build(BuildContext context) {
+    return FrostedCard(
+      child: Column(
+        crossAxisAlignment: CrossAxisAlignment.start,
+        children: <Widget>[
+          Row(
+            children: <Widget>[
+              const Icon(
+                Icons.event_available_rounded,
+                color: Color(0xFF2B7FFF),
+              ),
+              const SizedBox(width: 10),
+              Expanded(
+                child: Text(
+                  'Upcoming Events',
+                  style: Theme.of(context).textTheme.titleLarge,
+                ),
+              ),
+              _CountPill(count: events.length),
+            ],
+          ),
+          const SizedBox(height: 12),
+          if (events.isEmpty)
+            Text(
+              'No grounded event suggestions in the next 30 days.',
+              style: Theme.of(
+                context,
+              ).textTheme.bodyMedium?.copyWith(color: AppTheme.textSecondary),
+            )
+          else
+            ...events.map(
+              (AiSuggestionDraft event) => _UpcomingEventPreview(
+                draft: event,
+                person: peopleById[event.personId],
+              ),
+            ),
+        ],
+      ),
+    );
+  }
+}
+
+class _UpcomingEventPreview extends StatelessWidget {
+  const _UpcomingEventPreview({required this.draft, required this.person});
+
+  final AiSuggestionDraft draft;
+  final PersonProfile? person;
+
+  @override
+  Widget build(BuildContext context) {
+    return Padding(
+      padding: const EdgeInsets.only(bottom: 12),
+      child: Container(
+        padding: const EdgeInsets.all(12),
+        decoration: BoxDecoration(
+          color: const Color(0xFFF5FAFB),
+          borderRadius: BorderRadius.circular(12),
+        ),
+        child: Row(
+          crossAxisAlignment: CrossAxisAlignment.start,
+          children: <Widget>[
+            Expanded(
+              child: Column(
+                crossAxisAlignment: CrossAxisAlignment.start,
+                children: <Widget>[
+                  Text(
+                    draft.title,
+                    maxLines: 2,
+                    overflow: TextOverflow.ellipsis,
+                    style: Theme.of(context).textTheme.titleSmall,
+                  ),
+                  const SizedBox(height: 4),
+                  Text(
+                    '${_shortDate(draft.suggestedFor!)} · ${person?.name ?? 'Unknown person'}',
+                    maxLines: 1,
+                    overflow: TextOverflow.ellipsis,
+                    style: Theme.of(context).textTheme.bodyMedium?.copyWith(
+                      color: AppTheme.textSecondary,
+                    ),
+                  ),
+                  if (draft.eventLocation != null &&
+                      draft.eventLocation!.trim().isNotEmpty) ...<Widget>[
+                    const SizedBox(height: 2),
+                    Text(
+                      draft.eventLocation!.trim(),
+                      maxLines: 1,
+                      overflow: TextOverflow.ellipsis,
+                      style: Theme.of(context).textTheme.bodySmall?.copyWith(
+                        color: AppTheme.textSecondary,
+                      ),
+                    ),
+                  ],
+                ],
+              ),
+            ),
+            const SizedBox(width: 8),
+            IconButton.filledTonal(
+              tooltip: 'Add to calendar',
+              onPressed: () => _addToCalendar(context),
+              icon: const Icon(Icons.calendar_month_rounded),
+            ),
+          ],
+        ),
+      ),
+    );
+  }
+
+  Future<void> _addToCalendar(BuildContext context) async {
+    final bool launched = await const CalendarEventLauncher()
+        .addSuggestionToCalendar(draft);
+    if (!context.mounted || launched) {
+      return;
+    }
+    ScaffoldMessenger.of(
+      context,
+    ).showSnackBar(const SnackBar(content: Text('Could not open calendar.')));
+  }
+}
+
+class _CountPill extends StatelessWidget {
+  const _CountPill({required this.count});
+
+  final int count;
+
+  @override
+  Widget build(BuildContext context) {
+    return Container(
+      padding: const EdgeInsets.symmetric(horizontal: 10, vertical: 4),
+      decoration: BoxDecoration(
+        color: const Color(0xFFEAF7FB),
+        borderRadius: BorderRadius.circular(99),
+      ),
+      child: Text(
+        '$count',
+        style: Theme.of(
+          context,
+        ).textTheme.labelLarge?.copyWith(color: AppTheme.primary),
+      ),
+    );
+  }
+}
+
 class _RelationshipGraphCard extends StatelessWidget {
  const _RelationshipGraphCard({required this.people, required this.compact});

@@ -2566,6 +2867,38 @@ String _shortName(String name) {
  return parts.first;
 }

+List<AiSuggestionDraft> _upcomingEventSuggestions(
+  List<AiSuggestionDraft> drafts,
+  DateTime now,
+) {
+  final DateTime today = DateTime(now.year, now.month, now.day);
+  final DateTime windowEnd = today.add(const Duration(days: 30));
+  final List<AiSuggestionDraft> events =
+      drafts
+          .where((AiSuggestionDraft draft) {
+            final DateTime? startsAt = draft.suggestedFor;
+            return draft.kind == AiSuggestionKind.eventIdea &&
+                draft.status == AiSuggestionStatus.pending &&
+                startsAt != null &&
+                !startsAt.isBefore(today) &&
+                startsAt.isBefore(windowEnd);
+          })
+          .toList(growable: false)
+        ..sort(
+          (AiSuggestionDraft a, AiSuggestionDraft b) =>
+              a.suggestedFor!.compareTo(b.suggestedFor!),
+        );
+  return events.take(5).toList(growable: false);
+}
+
+String _compactShareText(String value) {
+  final String compact = value.trim().replaceAll(RegExp(r'\s+'), ' ');
+  if (compact.length <= 120) {
+    return compact;
+  }
+  return '${compact.substring(0, 117).trim()}...';
+}
+
 String _shortDate(DateTime value) {
  const List<String> weekdays = <String>[
    'Mon',
@@ -1,8 +1,10 @@
 import 'package:flutter/material.dart';
+import 'package:flutter/services.dart';
 import 'package:flutter_riverpod/flutter_riverpod.dart';
 import 'package:relationship_saver/core/config/app_config.dart';
 import 'package:relationship_saver/core/config/app_theme.dart';
 import 'package:relationship_saver/core/llm/llm_config.dart';
+import 'package:relationship_saver/core/llm/llm_diagnostics_log.dart';
 import 'package:relationship_saver/core/llm/llm_service.dart';
 import 'package:relationship_saver/features/ai_digest/application/llm_digest_background_scheduler.dart';
 import 'package:relationship_saver/features/ai_digest/application/llm_digest_orchestrator.dart';
@@ -114,7 +116,15 @@ class SettingsView extends ConsumerWidget {
                      const SizedBox(height: 12),
                      _SettingRow(
                        compact: compact,
-                        label: 'AI network',
+                        label: 'AI grounding',
+                        value: digestConfig.enableWebSearch
+                            ? 'Google Search enabled'
+                            : 'Model only',
+                      ),
+                      const SizedBox(height: 12),
+                      _SettingRow(
+                        compact: compact,
+                        label: 'Scheduled AI network',
                        value:
                            '${digestConfig.requireWifi ? 'Wi-Fi' : 'Any network'} + ${digestConfig.requireCharging ? 'charging' : 'battery allowed'}',
                      ),
@@ -150,6 +160,19 @@ class SettingsView extends ConsumerWidget {
                                  : 'Enable Weekly AI Digest',
                            ),
                          ),
+                          OutlinedButton.icon(
+                            onPressed: () => _toggleWebSearch(context, ref),
+                            icon: Icon(
+                              digestConfig.enableWebSearch
+                                  ? Icons.public_off_rounded
+                                  : Icons.public_rounded,
+                            ),
+                            label: Text(
+                              digestConfig.enableWebSearch
+                                  ? 'Disable Web Grounding'
+                                  : 'Enable Web Grounding',
+                            ),
+                          ),
                          OutlinedButton.icon(
                            onPressed: ref.watch(llmConfigProvider).isConfigured
                                ? () => _runPrivateDigest(context, ref)
@@ -319,6 +342,26 @@ class SettingsView extends ConsumerWidget {
    );
  }

+  Future<void> _toggleWebSearch(BuildContext context, WidgetRef ref) async {
+    final LlmDigestConfigState current = ref.read(llmDigestConfigProvider);
+    final bool nextEnabled = !current.enableWebSearch;
+    await ref
+        .read(llmDigestConfigProvider.notifier)
+        .setWebSearchEnabled(nextEnabled);
+    if (!context.mounted) {
+      return;
+    }
+    ScaffoldMessenger.of(context).showSnackBar(
+      SnackBar(
+        content: Text(
+          nextEnabled
+              ? 'Web grounding enabled for private digest.'
+              : 'Web grounding disabled for private digest.',
+        ),
+      ),
+    );
+  }
+
  Future<void> _showLlmDebug(BuildContext context) async {
    await showDialog<void>(
      context: context,
@@ -891,8 +934,10 @@ class _LlmDebugDialog extends ConsumerStatefulWidget {
 class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
  late final TextEditingController _promptController;
  bool _running = false;
+  bool _loadingEvents = true;
  String? _response;
  String? _error;
+  List<LlmDiagnosticsEvent> _events = const <LlmDiagnosticsEvent>[];

  @override
  void initState() {
@@ -900,6 +945,7 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
    _promptController = TextEditingController(
      text: 'Reply with one short sentence confirming the connection works.',
    );
+    _loadDiagnostics();
  }

  @override
@@ -958,6 +1004,44 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
                  ),
                ),
              ],
+              const SizedBox(height: 18),
+              Row(
+                children: <Widget>[
+                  Expanded(
+                    child: Text(
+                      'Recent diagnostics',
+                      style: Theme.of(context).textTheme.titleMedium,
+                    ),
+                  ),
+                  TextButton.icon(
+                    onPressed: _events.isEmpty ? null : _copyDiagnostics,
+                    icon: const Icon(Icons.copy_rounded),
+                    label: const Text('Copy'),
+                  ),
+                  TextButton.icon(
+                    onPressed: _events.isEmpty ? null : _clearDiagnostics,
+                    icon: const Icon(Icons.delete_outline_rounded),
+                    label: const Text('Clear'),
+                  ),
+                ],
+              ),
+              const SizedBox(height: 8),
+              if (_loadingEvents)
+                const LinearProgressIndicator()
+              else if (_events.isEmpty)
+                Text(
+                  'No LLM diagnostics recorded yet.',
+                  style: Theme.of(context).textTheme.bodyMedium?.copyWith(
+                    color: AppTheme.textSecondary,
+                  ),
+                )
+              else
+                ..._events
+                    .take(8)
+                    .map(
+                      (LlmDiagnosticsEvent event) =>
+                          _LlmDiagnosticsEventTile(event: event),
+                    ),
            ],
          ),
        ),
@@ -976,6 +1060,40 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
    );
  }

+  Future<void> _loadDiagnostics() async {
+    final List<LlmDiagnosticsEvent> events = await ref
+        .read(llmDiagnosticsLogProvider)
+        .read();
+    if (!mounted) {
+      return;
+    }
+    setState(() {
+      _events = events;
+      _loadingEvents = false;
+    });
+  }
+
+  Future<void> _copyDiagnostics() async {
+    final LlmDiagnosticsLog log = ref.read(llmDiagnosticsLogProvider);
+    await Clipboard.setData(ClipboardData(text: log.exportText(_events)));
+    if (!mounted) {
+      return;
+    }
+    ScaffoldMessenger.of(
+      context,
+    ).showSnackBar(const SnackBar(content: Text('LLM diagnostics copied.')));
+  }
+
+  Future<void> _clearDiagnostics() async {
+    await ref.read(llmDiagnosticsLogProvider).clear();
+    if (!mounted) {
+      return;
+    }
+    setState(() {
+      _events = const <LlmDiagnosticsEvent>[];
+    });
+  }
+
  Future<void> _runDebugPrompt() async {
    setState(() {
      _running = true;
@@ -996,6 +1114,7 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
      setState(() {
        _response = response;
      });
+      await _loadDiagnostics();
    } catch (error) {
      if (!mounted) {
        return;
@@ -1003,6 +1122,7 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
      setState(() {
        _error = error.toString();
      });
+      await _loadDiagnostics();
    } finally {
      if (mounted) {
        setState(() {
@@ -1013,6 +1133,46 @@ class _LlmDebugDialogState extends ConsumerState<_LlmDebugDialog> {
  }
 }

+class _LlmDiagnosticsEventTile extends StatelessWidget {
+  const _LlmDiagnosticsEventTile({required this.event});
+
+  final LlmDiagnosticsEvent event;
+
+  @override
+  Widget build(BuildContext context) {
+    return Container(
+      width: double.infinity,
+      margin: const EdgeInsets.only(bottom: 8),
+      padding: const EdgeInsets.all(10),
+      decoration: BoxDecoration(
+        border: Border.all(color: Theme.of(context).dividerColor),
+        borderRadius: BorderRadius.circular(6),
+      ),
+      child: Column(
+        crossAxisAlignment: CrossAxisAlignment.start,
+        children: <Widget>[
+          Text(
+            '${event.stage} · ${event.at.toLocal().toIso8601String()}',
+            style: Theme.of(context).textTheme.labelMedium,
+          ),
+          const SizedBox(height: 4),
+          SelectableText(event.message),
+          if (event.details != null &&
+              event.details!.trim().isNotEmpty) ...<Widget>[
+            const SizedBox(height: 6),
+            SelectableText(
+              event.details!,
+              style: Theme.of(
+                context,
+              ).textTheme.bodySmall?.copyWith(color: AppTheme.textSecondary),
+            ),
+          ],
+        ],
+      ),
+    );
+  }
+}
+
 class _LlmDebugConnectionSummary extends StatelessWidget {
  const _LlmDebugConnectionSummary({required this.config});

@@ -38,6 +38,7 @@ class SharedPayload {
    required this.createdAt,
    required this.receivedAt,
    required this.platform,
+    this.sharedMessageDateTime,
    this.url,
    this.sourceDisplayName,
    this.sourceUserId,
@@ -53,6 +54,7 @@ class SharedPayload {
  final String? url;
  final DateTime createdAt;
  final DateTime receivedAt;
+  final DateTime? sharedMessageDateTime;
  final String platform;
  final String? sourceDisplayName;
  final String? sourceUserId;
@@ -68,6 +70,7 @@ class SharedPayload {
    String? url,
    DateTime? createdAt,
    DateTime? receivedAt,
+    DateTime? sharedMessageDateTime,
    String? platform,
    String? sourceDisplayName,
    String? sourceUserId,
@@ -83,6 +86,8 @@ class SharedPayload {
      url: url ?? this.url,
      createdAt: createdAt ?? this.createdAt,
      receivedAt: receivedAt ?? this.receivedAt,
+      sharedMessageDateTime:
+          sharedMessageDateTime ?? this.sharedMessageDateTime,
      platform: platform ?? this.platform,
      sourceDisplayName: sourceDisplayName ?? this.sourceDisplayName,
      sourceUserId: sourceUserId ?? this.sourceUserId,
@@ -101,6 +106,7 @@ class SharedPayload {
      'url': url,
      'createdAt': createdAt.toUtc().toIso8601String(),
      'receivedAt': receivedAt.toUtc().toIso8601String(),
+      'sharedMessageDateTime': sharedMessageDateTime?.toUtc().toIso8601String(),
      'platform': platform,
      'sourceDisplayName': sourceDisplayName,
      'sourceUserId': sourceUserId,
@@ -130,6 +136,9 @@ class SharedPayload {
        json['receivedAt'] as String? ??
            DateTime.now().toUtc().toIso8601String(),
      ).toLocal(),
+      sharedMessageDateTime: json['sharedMessageDateTime'] == null
+          ? null
+          : DateTime.parse(json['sharedMessageDateTime'] as String).toLocal(),
      platform: json['platform'] as String? ?? 'unknown',
      sourceDisplayName: json['sourceDisplayName'] as String?,
      sourceUserId: json['sourceUserId'] as String?,
@@ -244,7 +253,8 @@ class SharedMessageEntry {

  String get sourceApp => payload.sourceApp;
  String get messageText => payload.rawText;
-  DateTime get sharedAt => payload.createdAt;
+  DateTime get sharedAt => payload.sharedMessageDateTime ?? payload.createdAt;
+  DateTime? get sharedMessageDateTime => payload.sharedMessageDateTime;
  SharedPayloadType get payloadType => payload.payloadType;
  String? get url => payload.url;
  String? get sourceDisplayName => payload.sourceDisplayName;
@@ -1,4 +1,5 @@
 import 'package:relationship_saver/features/local/local_models.dart';
+import 'package:relationship_saver/features/share_intake/domain/shared_message_datetime_extractor.dart';
 import 'package:relationship_saver/features/share_intake/domain/signal_share_parser.dart';
 import 'package:relationship_saver/features/share_intake/whatsapp_share_parser.dart';

@@ -20,6 +21,8 @@ class SharePayloadParser {
    final DateTime now = DateTime.now();
    final String normalizedSourceApp = _normalizeSourceApp(sourceApp);
    final String trimmed = rawText.trim();
+    final DateTime? sharedMessageDateTime =
+        SharedMessageDateTimeExtractor.extract(trimmed, now: receivedAt ?? now);
    final _ParsedSourceMetadata? sourceMetadata = _parseSourceMetadata(
      sourceApp: normalizedSourceApp,
      rawText: trimmed,
@@ -48,6 +51,7 @@ class SharePayloadParser {
      url: url,
      createdAt: createdAt ?? now,
      receivedAt: receivedAt ?? now,
+      sharedMessageDateTime: sharedMessageDateTime,
      platform: platform,
      sourceDisplayName: sourceMetadata?.sourceDisplayName,
      sourceUserId: sourceMetadata?.sourceUserId,
@@ -56,11 +60,14 @@ class SharePayloadParser {
        if (normalizedSourceApp != 'share_sheet')
          'source_app_$normalizedSourceApp',
        if (url != null) 'contains_url',
+        if (sharedMessageDateTime != null) 'shared_message_datetime_detected',
        if (sourceMetadata?.sourceDisplayName case final String _)
          'sender_detected',
      ],
      metadata: <String, String>{
        if (url case final String value) 'primaryUrl': value,
+        if (sharedMessageDateTime case final DateTime value)
+          'shared_message_datetime': value.toUtc().toIso8601String(),
      },
    );
  }
@@ -0,0 +1,377 @@
+/// Best-effort extraction of the original message timestamp from shared text.
+///
+/// This intentionally prefers source-message metadata shapes (chat export
+/// prefixes, bracketed timestamps, and explicit sent/received labels). It avoids
+/// treating arbitrary content dates like "birthday is May 20" as the time the
+/// message was received.
+class SharedMessageDateTimeExtractor {
+  const SharedMessageDateTimeExtractor._();
+
+  static final RegExp _isoDateTimePattern = RegExp(
+    r'(\d{4}-\d{1,2}-\d{1,2})(?:[tT\s]+(\d{1,2}:\d{2}(?::\d{2})?(?:\.\d+)?)(?:\s*(Z|[+-]\d{2}:?\d{2}))?)?',
+  );
+
+  static final RegExp _numericDatePattern = RegExp(
+    r'(\d{1,2})[./-](\d{1,2})[./-](\d{2,4})(?:[,\s]+(?:at\s+)?(\d{1,2})(?::(\d{2}))?(?::(\d{2}))?\s*(AM|PM|am|pm)?)?',
+  );
+
+  static final RegExp _monthNameDatePattern = RegExp(
+    r'(?:(\d{1,2})(?:st|nd|rd|th)?\s+([A-Za-zÀ-ž.]+)\s*,?\s*(\d{2,4})|([A-Za-zÀ-ž.]+)\s+(\d{1,2})(?:st|nd|rd|th)?[,]?\s*(\d{2,4}))(?:[,\s]+(?:at\s+)?(\d{1,2})(?::(\d{2}))?(?::(\d{2}))?\s*(AM|PM|am|pm)?)?',
+  );
+
+  static final RegExp _sourcePrefixPattern = RegExp(
+    r'^\s*(?:\[([^\]]{3,80})\]|([^-–—\n]{3,80}))\s*(?:[-–—]\s*)?([^:\n]{2,80}):\s+.+$',
+    dotAll: true,
+  );
+
+  static final RegExp _labelledLinePattern = RegExp(
+    r'^\s*(?:sent|sent at|received|received at|date|datetime|timestamp|message date|message time)\s*[:=-]\s*(.+)$',
+    caseSensitive: false,
+  );
+
+  static final RegExp _relativeLabelPattern = RegExp(
+    r'\b(today|yesterday)\b(?:\s+at)?\s+(\d{1,2})(?::(\d{2}))(?::(\d{2}))?\s*(AM|PM|am|pm)?',
+    caseSensitive: false,
+  );
+
+  static final Map<String, int> _months = <String, int>{
+    'jan': 1,
+    'january': 1,
+    'januar': 1,
+    'januari': 1,
+    'janvier': 1,
+    'feb': 2,
+    'february': 2,
+    'februar': 2,
+    'februari': 2,
+    'fevrier': 2,
+    'février': 2,
+    'mar': 3,
+    'march': 3,
+    'märz': 3,
+    'marz': 3,
+    'maerz': 3,
+    'mars': 3,
+    'apr': 4,
+    'april': 4,
+    'avr': 4,
+    'avril': 4,
+    'may': 5,
+    'mai': 5,
+    'maj': 5,
+    'jun': 6,
+    'june': 6,
+    'juni': 6,
+    'juin': 6,
+    'jul': 7,
+    'july': 7,
+    'juli': 7,
+    'juillet': 7,
+    'aug': 8,
+    'august': 8,
+    'aout': 8,
+    'août': 8,
+    'sep': 9,
+    'sept': 9,
+    'september': 9,
+    'septembre': 9,
+    'okt': 10,
+    'oct': 10,
+    'october': 10,
+    'oktober': 10,
+    'octobre': 10,
+    'nov': 11,
+    'november': 11,
+    'novembre': 11,
+    'dec': 12,
+    'dez': 12,
+    'december': 12,
+    'dezember': 12,
+    'decembre': 12,
+    'décembre': 12,
+  };
+
+  static DateTime? extract(String rawText, {DateTime? now}) {
+    try {
+      return _extract(rawText, now: now ?? DateTime.now());
+    } catch (_) {
+      return null;
+    }
+  }
+
+  static DateTime? _extract(String rawText, {required DateTime now}) {
+    final String input = rawText.trim();
+    if (input.isEmpty) {
+      return null;
+    }
+
+    for (final String candidate in _candidateFragments(input)) {
+      final DateTime? parsed = _parseDateTime(candidate, now: now);
+      if (parsed != null) {
+        return parsed;
+      }
+    }
+
+    final RegExpMatch? sourcePrefix = _sourcePrefixPattern.firstMatch(input);
+    if (sourcePrefix != null) {
+      for (final String? group in <String?>[
+        sourcePrefix.group(1),
+        sourcePrefix.group(2),
+      ]) {
+        if (group == null) {
+          continue;
+        }
+        final DateTime? parsed = _parseDateTime(group, now: now);
+        if (parsed != null) {
+          return parsed;
+        }
+      }
+    }
+
+    return null;
+  }
+
+  static List<String> _candidateFragments(String input) {
+    final List<String> candidates = <String>[];
+    final List<String> lines = input
+        .split(RegExp(r'\r?\n'))
+        .map((String line) => line.trim())
+        .where((String line) => line.isNotEmpty)
+        .take(6)
+        .toList(growable: false);
+
+    for (final String line in lines) {
+      final RegExpMatch? labelled = _labelledLinePattern.firstMatch(line);
+      if (labelled != null) {
+        candidates.add(labelled.group(1)!.trim());
+      }
+
+      if (line.startsWith('[') && line.contains(']')) {
+        final int end = line.indexOf(']');
+        candidates.add(line.substring(1, end).trim());
+      }
+
+      final int dashIndex = _firstSeparatorIndex(line);
+      final int colonIndex = line.indexOf(':');
+      if (dashIndex > 0 && dashIndex <= 80) {
+        candidates.add(line.substring(0, dashIndex).trim());
+      } else if (colonIndex > 0 && colonIndex <= 80) {
+        candidates.add(line.substring(0, colonIndex).trim());
+      }
+
+      candidates.add(line);
+    }
+
+    return candidates;
+  }
+
+  static int _firstSeparatorIndex(String value) {
+    final List<int> indexes = <int>[
+      value.indexOf(' - '),
+      value.indexOf(' – '),
+      value.indexOf(' — '),
+    ].where((int index) => index >= 0).toList(growable: false);
+    if (indexes.isEmpty) {
+      return -1;
+    }
+    indexes.sort();
+    return indexes.first;
+  }
+
+  static DateTime? _parseDateTime(String raw, {required DateTime now}) {
+    String value = raw
+        .trim()
+        .replaceFirst(RegExp(r'^[A-Za-z]{3,9},\s+'), '')
+        .replaceAll(RegExp(r'\s+'), ' ');
+    value = value.replaceAll(' um ', ' at ');
+    value = value.replaceAll(' à ', ' at ');
+
+    final RegExpMatch? relative = _relativeLabelPattern.firstMatch(value);
+    if (relative != null) {
+      final DateTime date = relative.group(1)!.toLowerCase() == 'yesterday'
+          ? now.subtract(const Duration(days: 1))
+          : now;
+      return _dateTimeOrNull(
+        date.year,
+        date.month,
+        date.day,
+        _hour(relative.group(2), relative.group(5)),
+        _intOrNull(relative.group(3)) ?? 0,
+        _intOrNull(relative.group(4)) ?? 0,
+      );
+    }
+
+    final RegExpMatch? iso = _isoDateTimePattern.firstMatch(value);
+    if (iso != null && _looksLikeMetadataFragment(value, iso.group(0)!)) {
+      final String date = iso.group(1)!;
+      final String? time = iso.group(2);
+      final String? zone = iso.group(3);
+      final String isoValue = time == null
+          ? date
+          : '${date}T$time${zone == null ? '' : _normalizeZone(zone)}';
+      final DateTime? parsed = DateTime.tryParse(isoValue);
+      if (parsed != null) {
+        return parsed.isUtc ? parsed.toLocal() : parsed;
+      }
+    }
+
+    final RegExpMatch? numeric = _numericDatePattern.firstMatch(value);
+    if (numeric != null &&
+        _looksLikeMetadataFragment(value, numeric.group(0)!)) {
+      final int first = int.parse(numeric.group(1)!);
+      final int second = int.parse(numeric.group(2)!);
+      final int year = _expandYear(int.parse(numeric.group(3)!));
+      final bool preferMonthFirst = _preferMonthFirst(value);
+      final int day;
+      final int month;
+      if (first > 12) {
+        day = first;
+        month = second;
+      } else if (second > 12) {
+        day = second;
+        month = first;
+      } else if (preferMonthFirst) {
+        day = second;
+        month = first;
+      } else {
+        day = first;
+        month = second;
+      }
+      return _dateTimeOrNull(
+        year,
+        month,
+        day,
+        _hour(numeric.group(4), numeric.group(7)),
+        _intOrNull(numeric.group(5)) ?? 0,
+        _intOrNull(numeric.group(6)) ?? 0,
+      );
+    }
+
+    final RegExpMatch? named = _monthNameDatePattern.firstMatch(value);
+    if (named != null && _looksLikeMetadataFragment(value, named.group(0)!)) {
+      final bool dayFirst = named.group(1) != null;
+      final int day = int.parse(dayFirst ? named.group(1)! : named.group(5)!);
+      final int? month = _monthNumber(
+        dayFirst ? named.group(2)! : named.group(4)!,
+      );
+      if (month == null) {
+        return null;
+      }
+      final int year = _expandYear(
+        int.parse(dayFirst ? named.group(3)! : named.group(6)!),
+      );
+      return _dateTimeOrNull(
+        year,
+        month,
+        day,
+        _hour(named.group(7), named.group(10)),
+        _intOrNull(named.group(8)) ?? 0,
+        _intOrNull(named.group(9)) ?? 0,
+      );
+    }
+
+    return null;
+  }
+
+  static bool _looksLikeMetadataFragment(String fragment, String match) {
+    final String value = fragment.trim();
+    if (value == match.trim()) {
+      return true;
+    }
+    if (value.startsWith(match)) {
+      final String tail = value.substring(match.length).trimLeft();
+      return tail.isEmpty ||
+          tail.startsWith('-') ||
+          tail.startsWith('–') ||
+          tail.startsWith('—') ||
+          tail.startsWith(']') ||
+          tail.startsWith(',') ||
+          tail.startsWith(':') ||
+          tail.toLowerCase().startsWith('at ');
+    }
+    return false;
+  }
+
+  static String _normalizeZone(String zone) {
+    if (zone == 'Z') {
+      return zone;
+    }
+    if (RegExp(r'^[+-]\d{4}$').hasMatch(zone)) {
+      return '${zone.substring(0, 3)}:${zone.substring(3)}';
+    }
+    return zone;
+  }
+
+  static bool _preferMonthFirst(String value) {
+    final String lower = value.toLowerCase();
+    return lower.contains('am') || lower.contains('pm');
+  }
+
+  static int _expandYear(int year) {
+    if (year >= 100) {
+      return year;
+    }
+    return year >= 70 ? 1900 + year : 2000 + year;
+  }
+
+  static int? _monthNumber(String raw) {
+    final String key = raw
+        .toLowerCase()
+        .replaceAll('.', '')
+        .replaceAll('ä', 'a')
+        .replaceAll('é', 'e')
+        .replaceAll('è', 'e')
+        .replaceAll('û', 'u')
+        .trim();
+    return _months[key] ?? _months[raw.toLowerCase().replaceAll('.', '')];
+  }
+
+  static int _hour(String? rawHour, String? meridiem) {
+    if (rawHour == null) {
+      return 0;
+    }
+    int hour = int.parse(rawHour);
+    final String? marker = meridiem?.toLowerCase();
+    if (marker == 'pm' && hour < 12) {
+      hour += 12;
+    }
+    if (marker == 'am' && hour == 12) {
+      hour = 0;
+    }
+    return hour;
+  }
+
+  static int? _intOrNull(String? value) {
+    if (value == null || value.isEmpty) {
+      return null;
+    }
+    return int.tryParse(value);
+  }
+
+  static DateTime? _dateTimeOrNull(
+    int year,
+    int month,
+    int day,
+    int hour,
+    int minute,
+    int second,
+  ) {
+    if (month < 1 ||
+        month > 12 ||
+        day < 1 ||
+        day > 31 ||
+        hour < 0 ||
+        hour > 23 ||
+        minute < 0 ||
+        minute > 59 ||
+        second < 0 ||
+        second > 59) {
+      return null;
+    }
+    final DateTime value = DateTime(year, month, day, hour, minute, second);
+    if (value.year != year || value.month != month || value.day != day) {
+      return null;
+    }
+    return value;
+  }
+}
@@ -8,6 +8,7 @@

 #include <flutter_secure_storage_linux/flutter_secure_storage_linux_plugin.h>
 #include <sentry_flutter/sentry_flutter_plugin.h>
+#include <url_launcher_linux/url_launcher_plugin.h>

 void fl_register_plugins(FlPluginRegistry* registry) {
  g_autoptr(FlPluginRegistrar) flutter_secure_storage_linux_registrar =
@@ -16,4 +17,7 @@ void fl_register_plugins(FlPluginRegistry* registry) {
  g_autoptr(FlPluginRegistrar) sentry_flutter_registrar =
      fl_plugin_registry_get_registrar_for_plugin(registry, "SentryFlutterPlugin");
  sentry_flutter_plugin_register_with_registrar(sentry_flutter_registrar);
+  g_autoptr(FlPluginRegistrar) url_launcher_linux_registrar =
+      fl_plugin_registry_get_registrar_for_plugin(registry, "UrlLauncherPlugin");
+  url_launcher_plugin_register_with_registrar(url_launcher_linux_registrar);
 }
@@ -5,6 +5,7 @@
 list(APPEND FLUTTER_PLUGIN_LIST
  flutter_secure_storage_linux
  sentry_flutter
+  url_launcher_linux
 )

 list(APPEND FLUTTER_FFI_PLUGIN_LIST
@@ -12,6 +12,7 @@ import flutter_secure_storage_darwin
 import package_info_plus
 import sentry_flutter
 import shared_preferences_foundation
+import url_launcher_macos

 func RegisterGeneratedPlugins(registry: FlutterPluginRegistry) {
  BatteryPlusMacosPlugin.register(with: registry.registrar(forPlugin: "BatteryPlusMacosPlugin"))
@@ -21,4 +22,5 @@ func RegisterGeneratedPlugins(registry: FlutterPluginRegistry) {
  FPPPackageInfoPlusPlugin.register(with: registry.registrar(forPlugin: "FPPPackageInfoPlusPlugin"))
  SentryFlutterPlugin.register(with: registry.registrar(forPlugin: "SentryFlutterPlugin"))
  SharedPreferencesPlugin.register(with: registry.registrar(forPlugin: "SharedPreferencesPlugin"))
+  UrlLauncherPlugin.register(with: registry.registrar(forPlugin: "UrlLauncherPlugin"))
 }
@@ -1,22 +1,73 @@
 PODS:
+  - battery_plus (0.0.1):
+    - FlutterMacOS
+  - connectivity_plus (0.0.1):
+    - FlutterMacOS
+  - flutter_local_notifications (0.0.1):
+    - FlutterMacOS
  - flutter_secure_storage_darwin (10.0.0):
    - Flutter
    - FlutterMacOS
  - FlutterMacOS (1.0.0)
+  - package_info_plus (0.0.1):
+    - FlutterMacOS
+  - Sentry/HybridSDK (8.46.0)
+  - sentry_flutter (8.14.2):
+    - Flutter
+    - FlutterMacOS
+    - Sentry/HybridSDK (= 8.46.0)
+  - shared_preferences_foundation (0.0.1):
+    - Flutter
+    - FlutterMacOS
+  - url_launcher_macos (0.0.1):
+    - FlutterMacOS

 DEPENDENCIES:
+  - battery_plus (from `Flutter/ephemeral/.symlinks/plugins/battery_plus/macos`)
+  - connectivity_plus (from `Flutter/ephemeral/.symlinks/plugins/connectivity_plus/macos`)
+  - flutter_local_notifications (from `Flutter/ephemeral/.symlinks/plugins/flutter_local_notifications/macos`)
  - flutter_secure_storage_darwin (from `Flutter/ephemeral/.symlinks/plugins/flutter_secure_storage_darwin/darwin`)
  - FlutterMacOS (from `Flutter/ephemeral`)
+  - package_info_plus (from `Flutter/ephemeral/.symlinks/plugins/package_info_plus/macos`)
+  - sentry_flutter (from `Flutter/ephemeral/.symlinks/plugins/sentry_flutter/macos`)
+  - shared_preferences_foundation (from `Flutter/ephemeral/.symlinks/plugins/shared_preferences_foundation/darwin`)
+  - url_launcher_macos (from `Flutter/ephemeral/.symlinks/plugins/url_launcher_macos/macos`)
+
+SPEC REPOS:
+  trunk:
+    - Sentry

 EXTERNAL SOURCES:
+  battery_plus:
+    :path: Flutter/ephemeral/.symlinks/plugins/battery_plus/macos
+  connectivity_plus:
+    :path: Flutter/ephemeral/.symlinks/plugins/connectivity_plus/macos
+  flutter_local_notifications:
+    :path: Flutter/ephemeral/.symlinks/plugins/flutter_local_notifications/macos
  flutter_secure_storage_darwin:
    :path: Flutter/ephemeral/.symlinks/plugins/flutter_secure_storage_darwin/darwin
  FlutterMacOS:
    :path: Flutter/ephemeral
+  package_info_plus:
+    :path: Flutter/ephemeral/.symlinks/plugins/package_info_plus/macos
+  sentry_flutter:
+    :path: Flutter/ephemeral/.symlinks/plugins/sentry_flutter/macos
+  shared_preferences_foundation:
+    :path: Flutter/ephemeral/.symlinks/plugins/shared_preferences_foundation/darwin
+  url_launcher_macos:
+    :path: Flutter/ephemeral/.symlinks/plugins/url_launcher_macos/macos

 SPEC CHECKSUMS:
+  battery_plus: f51ad29136e025b714b96f7d096f44f604615da7
+  connectivity_plus: 4adf20a405e25b42b9c9f87feff8f4b6fde18a4e
+  flutter_local_notifications: 4bf37a31afde695b56091b4ae3e4d9c7a7e6cda0
  flutter_secure_storage_darwin: acdb3f316ed05a3e68f856e0353b133eec373a23
  FlutterMacOS: d0db08ddef1a9af05a5ec4b724367152bb0500b1
+  package_info_plus: f0052d280d17aa382b932f399edf32507174e870
+  Sentry: da60d980b197a46db0b35ea12cb8f39af48d8854
+  sentry_flutter: 27892878729f42701297c628eb90e7c6529f3684
+  shared_preferences_foundation: 7036424c3d8ec98dfe75ff1667cb0cd531ec82bb
+  url_launcher_macos: f87a979182d112f911de6820aefddaf56ee9fbfd

 PODFILE CHECKSUM: 54d867c82ac51cbd61b565781b9fada492027009

@@ -1029,6 +1029,70 @@ packages:
      url: "https://pub.dev"
    source: hosted
    version: "1.0.0"
+  url_launcher:
+    dependency: "direct main"
+    description:
+      name: url_launcher
+      sha256: f6a7e5c4835bb4e3026a04793a4199ca2d14c739ec378fdfe23fc8075d0439f8
+      url: "https://pub.dev"
+    source: hosted
+    version: "6.3.2"
+  url_launcher_android:
+    dependency: transitive
+    description:
+      name: url_launcher_android
+      sha256: "3bb000251e55d4a209aa0e2e563309dc9bb2befea2295fd0cec1f51760aac572"
+      url: "https://pub.dev"
+    source: hosted
+    version: "6.3.29"
+  url_launcher_ios:
+    dependency: transitive
+    description:
+      name: url_launcher_ios
+      sha256: "580fe5dfb51671ae38191d316e027f6b76272b026370708c2d898799750a02b0"
+      url: "https://pub.dev"
+    source: hosted
+    version: "6.4.1"
+  url_launcher_linux:
+    dependency: transitive
+    description:
+      name: url_launcher_linux
+      sha256: d5e14138b3bc193a0f63c10a53c94b91d399df0512b1f29b94a043db7482384a
+      url: "https://pub.dev"
+    source: hosted
+    version: "3.2.2"
+  url_launcher_macos:
+    dependency: transitive
+    description:
+      name: url_launcher_macos
+      sha256: "368adf46f71ad3c21b8f06614adb38346f193f3a59ba8fe9a2fd74133070ba18"
+      url: "https://pub.dev"
+    source: hosted
+    version: "3.2.5"
+  url_launcher_platform_interface:
+    dependency: transitive
+    description:
+      name: url_launcher_platform_interface
+      sha256: "552f8a1e663569be95a8190206a38187b531910283c3e982193e4f2733f01029"
+      url: "https://pub.dev"
+    source: hosted
+    version: "2.3.2"
+  url_launcher_web:
+    dependency: transitive
+    description:
+      name: url_launcher_web
+      sha256: "85c81589622fbc87c1c683aaea164d3604a7777495a79d91e39ffcdec39ddb34"
+      url: "https://pub.dev"
+    source: hosted
+    version: "2.4.3"
+  url_launcher_windows:
+    dependency: transitive
+    description:
+      name: url_launcher_windows
+      sha256: "712c70ab1b99744ff066053cbe3e80c73332b38d46e5e945c98689b2e66fc15f"
+      url: "https://pub.dev"
+    source: hosted
+    version: "3.1.5"
  uuid:
    dependency: "direct main"
    description:
@@ -50,6 +50,7 @@ dependencies:
  flutter_local_notifications: ^20.1.0
  workmanager: ^0.9.0+3
  sentry_flutter: ^8.14.2
+  url_launcher: ^6.3.2

 dev_dependencies:
  flutter_test:
@@ -0,0 +1,41 @@
+import 'package:flutter_test/flutter_test.dart';
+import 'package:relationship_saver/core/llm/llm_diagnostics_log.dart';
+import 'package:shared_preferences/shared_preferences.dart';
+
+void main() {
+  setUp(() {
+    SharedPreferences.setMockInitialValues(<String, Object>{});
+  });
+
+  test('records and exports LLM diagnostics', () async {
+    const LlmDiagnosticsLog log = LlmDiagnosticsLog();
+
+    await log.record(
+      'provider_error',
+      'Google AI request failed with 429.',
+      details: '{"statusCode":429,"responseBody":"quota"}',
+    );
+
+    final List<LlmDiagnosticsEvent> events = await log.read();
+
+    expect(events, hasLength(1));
+    expect(events.single.stage, 'provider_error');
+    expect(events.single.details, contains('statusCode'));
+    expect(log.exportText(events), contains('Google AI request failed'));
+  });
+
+  test('trims very large diagnostics before storing', () async {
+    const LlmDiagnosticsLog log = LlmDiagnosticsLog();
+
+    await log.record(
+      'provider_error',
+      'large',
+      details: List<String>.filled(9000, 'x').join(),
+    );
+
+    final List<LlmDiagnosticsEvent> events = await log.read();
+
+    expect(events.single.details, endsWith('[truncated]'));
+    expect(events.single.details!.length, lessThan(9000));
+  });
+}
@@ -0,0 +1,125 @@
+import 'dart:convert';
+import 'dart:typed_data';
+
+import 'package:dio/dio.dart';
+import 'package:flutter_test/flutter_test.dart';
+import 'package:relationship_saver/core/llm/ollama/ollama_tool_chat_client.dart';
+import 'package:relationship_saver/core/llm/ollama/ollama_web_search_client.dart';
+import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
+
+import '../../helpers/queue_http_client_adapter.dart';
+
+void main() {
+  test(
+    'runs Ollama tool calls and feeds search results back to model',
+    () async {
+      final List<Map<String, dynamic>> requestBodies = <Map<String, dynamic>>[];
+      final QueueHttpClientAdapter adapter = QueueHttpClientAdapter(
+        <AdapterHandler>[
+          (
+            RequestOptions options,
+            Stream<Uint8List>? requestStream,
+            Future<void>? cancelFuture,
+          ) async {
+            requestBodies.add(
+              jsonDecode(options.data as String) as Map<String, dynamic>,
+            );
+            return jsonResponse(200, <String, dynamic>{
+              'message': <String, dynamic>{
+                'role': 'assistant',
+                'content': '',
+                'tool_calls': <Map<String, dynamic>>[
+                  <String, dynamic>{
+                    'function': <String, dynamic>{
+                      'name': 'search_web',
+                      'arguments': <String, dynamic>{
+                        'query': 'Zurich jazz events May 2026',
+                        'maxResults': 3,
+                      },
+                    },
+                  },
+                ],
+              },
+            });
+          },
+          (
+            RequestOptions options,
+            Stream<Uint8List>? requestStream,
+            Future<void>? cancelFuture,
+          ) async {
+            requestBodies.add(
+              jsonDecode(options.data as String) as Map<String, dynamic>,
+            );
+            return jsonResponse(200, <String, dynamic>{
+              'message': <String, dynamic>{
+                'role': 'assistant',
+                'content': '''
+{
+  "suggestions": [
+    {
+      "personToken": "person_001",
+      "kind": "eventIdea",
+      "title": "Jazz night",
+      "details": "A grounded event suggestion.",
+      "confidence": 0.8
+    }
+  ]
+}
+''',
+              },
+            });
+          },
+        ],
+      );
+      final Dio dio = Dio();
+      dio.httpClientAdapter = adapter;
+      final OllamaToolChatClient client = OllamaToolChatClient(
+        dio: dio,
+        webSearchClient: const FakeWebSearchClient(),
+      );
+
+      final String response = await client.complete(
+        baseUrl: 'http://macbook.local:11434',
+        model: 'qwen3:8b',
+        systemPrompt: 'Return digest JSON.',
+        userPrompt: '{"people":[]}',
+      );
+
+      expect(response, contains(AiSuggestionKind.eventIdea.name));
+      expect(adapter.fetchCount, 2);
+      expect(requestBodies.first['tools'], isA<List<dynamic>>());
+      final List<dynamic> secondMessages =
+          requestBodies.last['messages'] as List<dynamic>;
+      final Map<String, dynamic> toolMessage = secondMessages
+          .whereType<Map<String, dynamic>>()
+          .singleWhere(
+            (Map<String, dynamic> message) => message['role'] == 'tool',
+          );
+      expect(toolMessage['tool_name'], 'search_web');
+      expect(toolMessage['content'], contains('moods.ch'));
+    },
+  );
+}
+
+class FakeWebSearchClient implements OllamaWebSearchClient {
+  const FakeWebSearchClient();
+
+  @override
+  Future<String> fetchPageText(String url) async {
+    return 'Fetched text for $url';
+  }
+
+  @override
+  Future<List<OllamaWebSearchResult>> search(
+    String query, {
+    int maxResults = 5,
+  }) async {
+    return const <OllamaWebSearchResult>[
+      OllamaWebSearchResult(
+        title: 'Moods Jazz Club',
+        url: 'https://www.moods.ch/',
+        snippet: 'Upcoming jazz concerts in Zurich.',
+      ),
+    ];
+  }
+}
@@ -10,10 +10,14 @@ void main() {
        "suggestions": [
          {
            "personToken": "person_001",
-            "kind": "giftIdea",
+            "kind": "eventIdea",
            "title": "Coffee tasting set",
            "details": "Pick a small local sampler.",
            "suggestedTiming": "2026-05-20T18:00:00Z",
+            "eventEndsAt": "2026-05-20T20:00:00Z",
+            "eventLocation": "Local roaster hall",
+            "eventUrl": "https://example.com/events/coffee",
+            "sourceUrls": ["https://example.com/events/coffee"],
            "confidence": 0.82,
            "reason": "Matches known interests."
          }
@@ -28,8 +32,13 @@ void main() {
    expect(result.success, isTrue);
    expect(result.drafts, hasLength(1));
    expect(result.drafts.single.personId, 'p-1');
-    expect(result.drafts.single.kind, AiSuggestionKind.giftIdea);
+    expect(result.drafts.single.kind, AiSuggestionKind.eventIdea);
    expect(result.drafts.single.status, AiSuggestionStatus.pending);
+    expect(result.drafts.single.eventLocation, 'Local roaster hall');
+    expect(result.drafts.single.eventUrl, 'https://example.com/events/coffee');
+    expect(result.drafts.single.sourceUrls, <String>[
+      'https://example.com/events/coffee',
+    ]);
  });

  test('rejects unknown person tokens and malformed items', () {
@@ -53,6 +53,7 @@ void main() {
            rawText: 'Raw private chat text',
            createdAt: DateTime(2026, 5, 1),
            receivedAt: DateTime(2026, 5, 1),
+            sharedMessageDateTime: DateTime.utc(2026, 2, 1, 10),
            platform: 'ios',
            sourceDisplayName: 'Alice Secret',
            sourceUserId: 'wa:alice',
@@ -73,6 +74,27 @@ void main() {
          updatedAt: DateTime(2026, 5, 1),
          isSensitive: true,
        ),
+        PersonFact(
+          id: 'pf-2',
+          personId: 'p-1',
+          type: CapturedFactType.giftIdea,
+          text: 'Alice wants ceramic espresso cups',
+          label: 'Coffee gear',
+          sourceKind: CaptureSourceKind.shareInbox,
+          sharedMessageId: 'sm-1',
+          createdAt: DateTime(2026, 5, 2),
+          updatedAt: DateTime(2026, 5, 2),
+        ),
+        PersonFact(
+          id: 'pf-3',
+          personId: 'p-1',
+          type: CapturedFactType.placeIdea,
+          text: 'Unreviewed ramen place',
+          sourceKind: CaptureSourceKind.shareSheet,
+          createdAt: DateTime(2026, 5, 3),
+          updatedAt: DateTime(2026, 5, 3),
+          needsReview: true,
+        ),
      ],
      aiSuggestionDrafts: <AiSuggestionDraft>[
        AiSuggestionDraft(
@@ -104,6 +126,14 @@ void main() {
    expect(prompt, isNot(contains('thread-secret')));
    expect(prompt, isNot(contains('Raw private chat text')));
    expect(prompt, isNot(contains('Secret medical detail')));
+    expect(prompt, contains('capturedFacts'));
+    expect(prompt, contains('shared_message_datetime'));
+    expect(prompt, contains('2026-02-01T10:00:00.000Z'));
+    expect(prompt, contains('about 3 months ago'));
+    expect(prompt, contains('ceramic espresso cups'));
+    expect(prompt, contains('coffee gear'));
+    expect(prompt, contains('this person wants ceramic espresso cups'));
+    expect(prompt, isNot(contains('unreviewed ramen place')));
    expect(prompt, contains('priorSuggestions'));
    expect(prompt, contains('jazz concert downtown'));
    expect(prompt, contains('dismissed'));
@@ -0,0 +1,53 @@
+import 'package:flutter_test/flutter_test.dart';
+import 'package:relationship_saver/features/ai_digest/application/calendar_event_launcher.dart';
+import 'package:relationship_saver/features/ai_digest/domain/ai_digest_models.dart';
+
+void main() {
+  test('builds Google Calendar template URL for event suggestions', () {
+    final Uri? uri = calendarUriForSuggestion(
+      AiSuggestionDraft(
+        id: 'ai-1',
+        personId: 'p-1',
+        kind: AiSuggestionKind.eventIdea,
+        title: 'Coffee festival',
+        details: 'Visit the tasting session.',
+        suggestedAt: DateTime(2026, 5, 16),
+        suggestedFor: DateTime.utc(2026, 5, 20, 18),
+        eventEndsAt: DateTime.utc(2026, 5, 20, 20),
+        eventLocation: 'Local roaster hall',
+        eventUrl: 'https://example.com/events/coffee',
+        sourceUrls: const <String>['https://example.com/events/coffee'],
+        confidence: 0.8,
+        status: AiSuggestionStatus.pending,
+        sourceRunId: 'run-1',
+      ),
+    );
+
+    expect(uri, isNotNull);
+    expect(uri!.host, 'calendar.google.com');
+    expect(uri.queryParameters['action'], 'TEMPLATE');
+    expect(uri.queryParameters['text'], 'Coffee festival');
+    expect(uri.queryParameters['dates'], '20260520T180000Z/20260520T200000Z');
+    expect(uri.queryParameters['location'], 'Local roaster hall');
+    expect(uri.queryParameters['details'], contains('Visit the tasting'));
+    expect(uri.queryParameters['details'], contains('https://example.com'));
+  });
+
+  test('does not build a calendar URL without event timing', () {
+    final Uri? uri = calendarUriForSuggestion(
+      AiSuggestionDraft(
+        id: 'ai-2',
+        personId: 'p-1',
+        kind: AiSuggestionKind.eventIdea,
+        title: 'Untimed event',
+        details: '',
+        suggestedAt: DateTime(2026, 5, 16),
+        confidence: 0.6,
+        status: AiSuggestionStatus.pending,
+        sourceRunId: 'run-1',
+      ),
+    );
+
+    expect(uri, isNull);
+  });
+}
@@ -71,6 +71,7 @@ void main() {
      expect(result.completed, isTrue);
      expect(result.createdDraftCount, 1);
      expect(textClient.calls, 1);
+      expect(textClient.lastEnableWebSearch, isTrue);
      expect(textClient.lastPrompt, isNot(contains(state.people.first.name)));
      expect(state.aiSuggestionDrafts, hasLength(1));
      expect(
@@ -120,6 +121,139 @@ void main() {
    expect(textClient.calls, 0);
  });

+  test('manual digest bypasses scheduled network policy', () async {
+    final FakeTextClient textClient = FakeTextClient(
+      response: '''
+      {
+        "suggestions": [
+          {
+            "personToken": "person_001",
+            "kind": "checkIn",
+            "title": "Send a quick note",
+            "details": "Ask how the week is going.",
+            "confidence": 0.7
+          }
+        ]
+      }
+      ''',
+    );
+    final ProviderContainer container = _createContainer(
+      textClient: textClient,
+      notifier: FakeNotifier(),
+      environment: const FakeEnvironment(canRunValue: false),
+    );
+    addTearDown(container.dispose);
+
+    await container.read(localRepositoryProvider.future);
+    await container
+        .read(localRepositoryProvider.notifier)
+        .addPerson(
+          name: 'Taylor Quinn',
+          relationship: 'Friend',
+          notes: '',
+          tags: const <String>['tea'],
+        );
+
+    final LlmDigestRunResult result = await container
+        .read(llmDigestOrchestratorProvider)
+        .runManualDigest();
+
+    expect(result.started, isTrue);
+    expect(result.completed, isTrue);
+    expect(textClient.calls, 1);
+  });
+
+  test('digest respects disabled web grounding setting', () async {
+    final FakeTextClient textClient = FakeTextClient(
+      response: '''
+      {
+        "suggestions": [
+          {
+            "personToken": "person_001",
+            "kind": "checkIn",
+            "title": "Send a quick note",
+            "details": "Ask how the week is going.",
+            "confidence": 0.7
+          }
+        ]
+      }
+      ''',
+    );
+    final ProviderContainer container = _createContainer(
+      textClient: textClient,
+      notifier: FakeNotifier(),
+    );
+    addTearDown(container.dispose);
+
+    await container.read(localRepositoryProvider.future);
+    await container
+        .read(localRepositoryProvider.notifier)
+        .addPerson(
+          name: 'Taylor Quinn',
+          relationship: 'Friend',
+          notes: '',
+          tags: const <String>['tea'],
+        );
+    await container
+        .read(llmDigestConfigProvider.notifier)
+        .setWebSearchEnabled(false);
+
+    final LlmDigestRunResult result = await container
+        .read(llmDigestOrchestratorProvider)
+        .runManualDigest();
+
+    expect(result.completed, isTrue);
+    expect(textClient.lastEnableWebSearch, isFalse);
+  });
+
+  test(
+    'digest retries without web grounding after grounded quota error',
+    () async {
+      final SequenceTextClient textClient = SequenceTextClient(<Object>[
+        const LlmProviderException(
+          provider: LlmProvider.google,
+          statusCode: 429,
+          message: 'Google AI rejected the digest request with 429 quota.',
+        ),
+        '''
+      {
+        "suggestions": [
+          {
+            "personToken": "person_001",
+            "kind": "checkIn",
+            "title": "Send a quick note",
+            "details": "Ask how the week is going.",
+            "confidence": 0.7
+          }
+        ]
+      }
+      ''',
+      ]);
+      final ProviderContainer container = _createContainer(
+        textClient: textClient,
+        notifier: FakeNotifier(),
+      );
+      addTearDown(container.dispose);
+
+      await container.read(localRepositoryProvider.future);
+      await container
+          .read(localRepositoryProvider.notifier)
+          .addPerson(
+            name: 'Taylor Quinn',
+            relationship: 'Friend',
+            notes: '',
+            tags: const <String>['tea'],
+          );
+
+      final LlmDigestRunResult result = await container
+          .read(llmDigestOrchestratorProvider)
+          .runManualDigest();
+
+      expect(result.completed, isTrue);
+      expect(textClient.enableWebSearchValues, <bool>[true, false]);
+    },
+  );
+
  test('manual digest reports provider rate limits without Dio noise', () async {
    final ThrowingTextClient textClient = ThrowingTextClient(
      error: const LlmProviderException(
@@ -183,14 +317,17 @@ class FakeTextClient implements LlmDigestTextClient {
  final String response;
  int calls = 0;
  String? lastPrompt;
+  bool? lastEnableWebSearch;

  @override
  Future<String> complete({
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  }) async {
    calls += 1;
    lastPrompt = userPrompt;
+    lastEnableWebSearch = enableWebSearch;
    return response;
  }
 }
@@ -204,11 +341,35 @@ class ThrowingTextClient implements LlmDigestTextClient {
  Future<String> complete({
    required String systemPrompt,
    required String userPrompt,
+    bool enableWebSearch = false,
  }) async {
    throw error;
  }
 }

+class SequenceTextClient implements LlmDigestTextClient {
+  SequenceTextClient(this.results);
+
+  final List<Object> results;
+  final List<bool> enableWebSearchValues = <bool>[];
+  int _index = 0;
+
+  @override
+  Future<String> complete({
+    required String systemPrompt,
+    required String userPrompt,
+    bool enableWebSearch = false,
+  }) async {
+    enableWebSearchValues.add(enableWebSearch);
+    final Object result = results[_index];
+    _index += 1;
+    if (result is Exception) {
+      throw result;
+    }
+    return result as String;
+  }
+}
+
 class FakeNotifier implements AiDigestNotifier {
  int? lastCount;

@@ -39,6 +39,33 @@ void main() {
    expect(payload.rawText, 'loves cozy Italian restaurants');
  });

+  test('stores source message datetime when WhatsApp text includes one', () {
+    final SharedPayload payload = SharePayloadParser.parse(
+      rawText: '[19/05/2026, 14:30] Ava Hart: ginger tea helped',
+      sourceApp: 'whatsapp',
+      platform: 'ios',
+    );
+
+    expect(payload.sourceDisplayName, 'Ava Hart');
+    expect(payload.rawText, 'ginger tea helped');
+    expect(payload.sharedMessageDateTime, DateTime(2026, 5, 19, 14, 30));
+    expect(payload.parsingHints, contains('shared_message_datetime_detected'));
+    expect(payload.metadata, contains('shared_message_datetime'));
+  });
+
+  test(
+    'does not store source message datetime for arbitrary content dates',
+    () {
+      final SharedPayload payload = SharePayloadParser.parse(
+        rawText: 'Ava birthday is on May 20 and she likes ginger tea.',
+        sourceApp: 'share_sheet',
+        platform: 'ios',
+      );
+
+      expect(payload.sharedMessageDateTime, isNull);
+    },
+  );
+
  test('uses explicit signal source app hint and extracts sender', () {
    final SharedPayload payload = SharePayloadParser.parse(
      rawText: 'Marek: this concert looks promising',
@@ -0,0 +1,58 @@
+import 'package:flutter_test/flutter_test.dart';
+import 'package:relationship_saver/features/share_intake/domain/shared_message_datetime_extractor.dart';
+
+void main() {
+  group('SharedMessageDateTimeExtractor', () {
+    test('extracts WhatsApp bracketed European timestamp', () {
+      final DateTime? value = SharedMessageDateTimeExtractor.extract(
+        '[19/05/2026, 14:30] Ava Hart: I was sick but ginger tea helped',
+      );
+
+      expect(value, DateTime(2026, 5, 19, 14, 30));
+    });
+
+    test('extracts exported chat prefix with US meridiem timestamp', () {
+      final DateTime? value = SharedMessageDateTimeExtractor.extract(
+        '5/19/26, 2:30 PM - Ava Hart: ginger tea helped',
+      );
+
+      expect(value, DateTime(2026, 5, 19, 14, 30));
+    });
+
+    test('extracts labelled month-name timestamp', () {
+      final DateTime? value = SharedMessageDateTimeExtractor.extract(
+        'Received at: 19 May 2026 at 14:30\nAva: ginger tea helped',
+      );
+
+      expect(value, DateTime(2026, 5, 19, 14, 30));
+    });
+
+    test(
+      'extracts relative labelled timestamp using provided reference date',
+      () {
+        final DateTime? value = SharedMessageDateTimeExtractor.extract(
+          'Yesterday at 21:05 - Ava Hart: ginger tea helped',
+          now: DateTime(2026, 5, 19, 9),
+        );
+
+        expect(value, DateTime(2026, 5, 18, 21, 5));
+      },
+    );
+
+    test('does not treat arbitrary content date as message timestamp', () {
+      final DateTime? value = SharedMessageDateTimeExtractor.extract(
+        'Ava birthday is on May 20 and she likes ginger tea.',
+      );
+
+      expect(value, isNull);
+    });
+
+    test('returns null instead of throwing for invalid dates', () {
+      final DateTime? value = SharedMessageDateTimeExtractor.extract(
+        '[99/99/2026, 25:99] Ava: impossible',
+      );
+
+      expect(value, isNull);
+    });
+  });
+}
@@ -10,6 +10,7 @@
 #include <connectivity_plus/connectivity_plus_windows_plugin.h>
 #include <flutter_secure_storage_windows/flutter_secure_storage_windows_plugin.h>
 #include <sentry_flutter/sentry_flutter_plugin.h>
+#include <url_launcher_windows/url_launcher_windows.h>

 void RegisterPlugins(flutter::PluginRegistry* registry) {
  BatteryPlusWindowsPluginRegisterWithRegistrar(
@@ -20,4 +21,6 @@ void RegisterPlugins(flutter::PluginRegistry* registry) {
      registry->GetRegistrarForPlugin("FlutterSecureStorageWindowsPlugin"));
  SentryFlutterPluginRegisterWithRegistrar(
      registry->GetRegistrarForPlugin("SentryFlutterPlugin"));
+  UrlLauncherWindowsRegisterWithRegistrar(
+      registry->GetRegistrarForPlugin("UrlLauncherWindows"));
 }
@@ -7,6 +7,7 @@ list(APPEND FLUTTER_PLUGIN_LIST
  connectivity_plus
  flutter_secure_storage_windows
  sentry_flutter
+  url_launcher_windows
 )

 list(APPEND FLUTTER_FFI_PLUGIN_LIST