feat: namedTimeout for Sentry context

lib/main.dart

@@ -256,6 +256,26 @@ FutureOr<SentryEvent?> _beforeSend(SentryEvent event, Hint _) {
     }
   }
 
+  // Enrich TimeoutException with operation name + duration as tags/fingerprint.
+  // value format: "TimeoutException after 0:00:05.000000: <operation> timed out"
+  if (exceptions != null) {
+    final timeoutException = exceptions.where((e) => e.type == 'TimeoutException').firstOrNull;
+    if (timeoutException != null) {
+      final value = timeoutException.value ?? '';
+      final colonIdx = value.indexOf(': ');
+      final message = colonIdx >= 0 ? value.substring(colonIdx + 2) : value;
+      final operation = message.endsWith(' timed out')
+          ? message.substring(0, message.length - ' timed out'.length)
+          : null;
+      final durationMatch = RegExp(r'after (\d+:\d{2}:\d{2}\.\d+)').firstMatch(value);
+
+      final tags = event.tags ??= {};
+      if (operation != null) tags['timeout.operation'] = operation;
+      if (durationMatch != null) tags['timeout.duration'] = durationMatch.group(1)!;
+      event.fingerprint = ['TimeoutException', ?operation];
+    }
+  }
+
   // Scrub breadcrumb messages and data
   final breadcrumbs = event.breadcrumbs;
   if (breadcrumbs != null) {

lib/services/discord_rpc_service.dart

@@ -5,8 +5,9 @@ import 'package:dart_discord_presence/dart_discord_presence.dart';
 import 'package:http/http.dart' as http;
 
 import '../models/plex_metadata.dart';
-import '../utils/plex_http_client.dart';
 import '../utils/app_logger.dart';
+import '../utils/future_extensions.dart';
+import '../utils/plex_http_client.dart';
 import 'plex_client.dart';
 import 'settings_service.dart';
 
@@ -317,7 +318,7 @@ class DiscordRPCService {
 
       final uploadStreamed = await httpClient.inner
           .send(uploadRequest)
-          .timeout(const Duration(seconds: 15));
+          .namedTimeout(const Duration(seconds: 15), operation: 'Litterbox upload');
       final uploadedUrl = (await uploadStreamed.stream.bytesToString()).trim();
 
       if (uploadedUrl.startsWith('http')) {

lib/services/multi_server_manager.dart

@@ -6,6 +6,7 @@ import 'plex_client.dart';
 import '../models/plex_config.dart';
 import '../utils/app_logger.dart';
 import '../utils/connection_constants.dart';
+import '../utils/future_extensions.dart';
 import 'package:sentry_flutter/sentry_flutter.dart';
 import 'plex_auth_service.dart';
 import 'settings_service.dart';
@@ -207,7 +208,7 @@ class MultiServerManager {
       try {
         appLogger.d('Attempting connection to server: ${server.name}');
 
-        final client = await _createClientForServer(server: server, clientIdentifier: effectiveClientId).timeout(timeout);
+        final client = await _createClientForServer(server: server, clientIdentifier: effectiveClientId).namedTimeout(timeout, operation: 'connect to ${server.name}');
 
         // Store the client and server info
         _clients[serverId]?.close();

lib/services/saf_storage_service.dart

@@ -3,6 +3,7 @@ import 'dart:io';
 
 import 'package:flutter/foundation.dart';
 import 'package:saf_util/saf_util.dart';
+import '../utils/future_extensions.dart';
 import '../utils/platform_detector.dart';
 import 'package:saf_util/saf_util_platform_interface.dart';
 import 'package:saf_stream/saf_stream.dart';
@@ -150,7 +151,7 @@ class SafStorageService {
       // This is much more efficient for large files and avoids hangs
       final result = await _safStream
           .pasteLocalFile(sourceFilePath, targetDirectoryUri, fileName, mimeType, overwrite: true)
-          .timeout(const Duration(minutes: 30), onTimeout: () => throw TimeoutException('SAF copy timed out'));
+          .namedTimeout(const Duration(minutes: 30), operation: 'SAF copy');
 
       debugPrint('SAF copyFileToSaf: successfully copied to ${result.uri}');
       return result.uri.toString();

lib/services/track_selection_service.dart

@@ -3,6 +3,7 @@ import 'dart:async';
 import '../mpv/mpv.dart';
 
 import '../models/plex_media_info.dart';
+import '../utils/future_extensions.dart';
 import '../models/plex_metadata.dart';
 import '../models/plex_user_profile.dart';
 import '../utils/app_logger.dart';
@@ -686,7 +687,7 @@ class TrackSelectionService {
         await player.streams.tracks
             .where((t) => t.audio.isNotEmpty || t.subtitle.isNotEmpty)
             .first
-            .timeout(const Duration(seconds: 10));
+            .namedTimeout(const Duration(seconds: 10), operation: 'track loading');
       } catch (_) {
         // Timeout or stream closed — proceed with whatever state we have
       }

lib/utils/plex_http_client.dart

@@ -6,6 +6,7 @@ import 'dart:typed_data';
 import 'package:http/http.dart' as http;
 
 import 'app_logger.dart';
+import 'future_extensions.dart';
 import 'isolate_helper.dart';
 import 'log_redaction_manager.dart';
 import 'plex_http_exception.dart';
@@ -145,11 +146,11 @@ class PlexHttpClient {
     try {
       final streamed = await _client
           .send(request)
-          .timeout(timeout ?? connectTimeout);
+          .namedTimeout(timeout ?? connectTimeout, operation: 'GET ${uri.path} connect');
 
       final bytes = await streamed.stream
           .toBytes()
-          .timeout(timeout ?? receiveTimeout);
+          .namedTimeout(timeout ?? receiveTimeout, operation: 'GET ${uri.path} receive');
 
       sw.stop();
       _logResponse('GET', uri, streamed.statusCode, sw.elapsedMilliseconds);
@@ -174,7 +175,7 @@ class PlexHttpClient {
     try {
       final streamed = await _client
           .send(request)
-          .timeout(timeout ?? connectTimeout);
+          .namedTimeout(timeout ?? connectTimeout, operation: 'download ${uri.path} connect');
 
       final file = File(filePath);
       final sink = file.openWrite();
@@ -231,12 +232,12 @@ class PlexHttpClient {
       // Phase 1: send + receive headers (connect timeout)
       final streamed = await _client
           .send(request)
-          .timeout(timeout ?? connectTimeout);
+          .namedTimeout(timeout ?? connectTimeout, operation: '$method ${uri.path} connect');
 
       // Phase 2: consume body (receive timeout)
       final bytes = await streamed.stream
           .toBytes()
-          .timeout(timeout ?? receiveTimeout);
+          .namedTimeout(timeout ?? receiveTimeout, operation: '$method ${uri.path} receive');
 
       sw.stop();
       _logResponse(method, uri, streamed.statusCode, sw.elapsedMilliseconds);