diff --git a/CLAUDE.md b/CLAUDE.md
index c049bdb..0eb6632 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -113,6 +113,7 @@ VapourBox/
 | `app/lib/services/filter_loader.dart` | Load filter schemas from JSON |
 | `app/lib/services/preset_service.dart` | Save/load user presets |
 | `app/lib/services/temp_directory_service.dart` | Configurable scratch-file directory (see "Temporary Files Directory") |
+| `app/lib/services/overwrite_behavior_service.dart` | Default action for existing output files (see "Existing Output Files") |
 | `app/assets/filters/core/*.json` | Built-in filter schema definitions |
 
 ## Build Commands
@@ -797,6 +798,23 @@ download.
 recreated; `setOverride` verifies writability with a probe file before accepting
 a path.
 
+### Existing Output Files (issue #85)
+
+Before a job starts, `_getConflictingItems` (`main_window.dart`) checks whether
+any queued item's `outputPath` already exists. What happens next is decided by
+`OverwriteBehaviorService` (persisted as `overwriteBehavior`, default `ask`,
+configurable in **Settings → General → Existing Output Files**):
+
+- **`ask`** (default) — shows `OverwriteWarningDialog`, which now also notes
+  where to change the default. Cancelling aborts the job.
+- **`overwrite`** — proceeds silently; the existing file is replaced.
+- **`rename`** — `OverwriteBehaviorService.uniquePath` picks the first free
+  `name (2).ext`, `name (3).ext`, … and each conflicting item's `outputPath` is
+  updated to it before the job starts; the existing file is untouched. Mutating
+  `QueueItem.outputPath` directly needs a `notifyListeners()` call afterward —
+  `MainViewModel.notifyOutputPathsChanged()` is that call for callers outside
+  the view model.
+
 ### Preset System
 
 Presets save complete filter pipeline + encoding settings. The built-in presets
diff --git a/README.md b/README.md
index e38cbd0..7a5e2a0 100644
--- a/README.md
+++ b/README.md
@@ -195,6 +195,13 @@ Scratch files — generated scripts, preview frames, job files, extracted DVD ti
 
 </details>
 
+<details>
+<summary><b>Existing output files</b></summary>
+
+When a job's output file already exists, VapourBox asks what to do by default. **Settings → General → Existing Output Files** can change that to always overwrite, or always write to a new, numbered filename (`name (2).ext`, `name (3).ext`, …) instead of touching the existing file. The dialog itself links back here.
+
+</details>
+
 ## Feedback and bug reports
 
 **Settings → General → "Report a bug or give feedback"** opens the issue tracker. Reports about specific problem sources are useful — several fixes in VapourBox came from them.
diff --git a/app/lib/main.dart b/app/lib/main.dart
index 8dc5ffd..b3ad9ce 100644
--- a/app/lib/main.dart
+++ b/app/lib/main.dart
@@ -7,6 +7,7 @@ import 'models/filter_registry.dart';
 import 'services/advanced_mode_service.dart';
 import 'services/dependency_manager.dart';
 import 'services/hardware_encoder_detector.dart';
+import 'services/overwrite_behavior_service.dart';
 import 'services/preset_service.dart';
 import 'services/temp_directory_service.dart';
 import 'services/tool_locator.dart';
@@ -30,6 +31,10 @@ void main() async {
   // settings don't flash from simple to advanced on startup.
   await AdvancedModeService.instance.initialize();
 
+  // Load the saved default for existing output files (issue #85) before the
+  // first job can be started.
+  await OverwriteBehaviorService.instance.initialize();
+
   // Initialize window manager for desktop
   await windowManager.ensureInitialized();
 
diff --git a/app/lib/services/overwrite_behavior_service.dart b/app/lib/services/overwrite_behavior_service.dart
new file mode 100644
index 0000000..3bec998
--- /dev/null
+++ b/app/lib/services/overwrite_behavior_service.dart
@@ -0,0 +1,109 @@
+import 'dart:io';
+
+import 'package:shared_preferences/shared_preferences.dart';
+
+/// What VapourBox should do when a job's output file already exists on disk
+/// (issue #85).
+enum OverwriteBehavior {
+  /// Show [OverwriteWarningDialog] and let the user decide each time.
+  ask,
+
+  /// Overwrite the existing file without asking.
+  overwrite,
+
+  /// Write to a new, non-colliding filename instead of touching the existing
+  /// file.
+  rename;
+
+  static OverwriteBehavior fromName(String? name) {
+    return OverwriteBehavior.values.firstWhere(
+      (behavior) => behavior.name == name,
+      orElse: () => OverwriteBehavior.ask,
+    );
+  }
+
+  String get label {
+    switch (this) {
+      case OverwriteBehavior.ask:
+        return 'Ask every time';
+      case OverwriteBehavior.overwrite:
+        return 'Overwrite';
+      case OverwriteBehavior.rename:
+        return 'Rename the new file';
+    }
+  }
+
+  String get description {
+    switch (this) {
+      case OverwriteBehavior.ask:
+        return 'Show a warning and let you choose before each job starts';
+      case OverwriteBehavior.overwrite:
+        return 'Replace the existing file without asking';
+      case OverwriteBehavior.rename:
+        return 'Keep the existing file and add a number to the new one';
+    }
+  }
+}
+
+/// Default action for output files that already exist, configurable in
+/// Settings -> General. Defaults to [OverwriteBehavior.ask], which preserves
+/// the previous (only) behavior of always showing
+/// `OverwriteWarningDialog`.
+class OverwriteBehaviorService {
+  static final OverwriteBehaviorService instance =
+      OverwriteBehaviorService._();
+  OverwriteBehaviorService._();
+
+  static const String _prefsKey = 'overwriteBehavior';
+
+  OverwriteBehavior _behavior = OverwriteBehavior.ask;
+  bool _loaded = false;
+
+  OverwriteBehavior get behavior => _behavior;
+
+  /// Load the saved choice. Safe to call again; only the first call reads
+  /// storage.
+  Future<void> initialize() async {
+    if (_loaded) return;
+    try {
+      final prefs = await SharedPreferences.getInstance();
+      _behavior = OverwriteBehavior.fromName(prefs.getString(_prefsKey));
+    } catch (_) {
+      // Unreadable preferences shouldn't stop the app starting - asking is
+      // the safe default to fall back to.
+      _behavior = OverwriteBehavior.ask;
+    }
+    _loaded = true;
+  }
+
+  Future<void> setBehavior(OverwriteBehavior value) async {
+    _behavior = value;
+    _loaded = true;
+    try {
+      final prefs = await SharedPreferences.getInstance();
+      await prefs.setString(_prefsKey, value.name);
+    } catch (_) {
+      // Keep the in-memory choice for this session even if it can't be saved.
+    }
+  }
+
+  /// Returns [path] unchanged if nothing exists there yet, otherwise the
+  /// first `name (2).ext`, `name (3).ext`, ... that doesn't.
+  Future<String> uniquePath(String path) async {
+    if (!await File(path).exists()) return path;
+
+    final separator = path.lastIndexOf(RegExp(r'[\\/]'));
+    final dir = separator >= 0 ? path.substring(0, separator + 1) : '';
+    final name = separator >= 0 ? path.substring(separator + 1) : path;
+    final dot = name.lastIndexOf('.');
+    final stem = dot > 0 ? name.substring(0, dot) : name;
+    final ext = dot > 0 ? name.substring(dot) : '';
+
+    var counter = 2;
+    while (true) {
+      final candidate = '$dir$stem ($counter)$ext';
+      if (!await File(candidate).exists()) return candidate;
+      counter++;
+    }
+  }
+}
diff --git a/app/lib/viewmodels/main_viewmodel.dart b/app/lib/viewmodels/main_viewmodel.dart
index 140a007..f03c611 100644
--- a/app/lib/viewmodels/main_viewmodel.dart
+++ b/app/lib/viewmodels/main_viewmodel.dart
@@ -737,6 +737,12 @@ class MainViewModel extends ChangeNotifier {
     notifyListeners();
   }
 
+  /// Call after mutating one or more queue items' `outputPath` directly
+  /// (e.g. auto-renaming to avoid an overwrite) so the UI reflects it.
+  void notifyOutputPathsChanged() {
+    notifyListeners();
+  }
+
   /// Clears the current input (alias for clearQueue).
   void clearInput() {
     clearQueue();
diff --git a/app/lib/views/main_window.dart b/app/lib/views/main_window.dart
index 5b5c8a5..68d90a9 100644
--- a/app/lib/views/main_window.dart
+++ b/app/lib/views/main_window.dart
@@ -9,6 +9,7 @@ import '../models/processing_preset.dart';
 import '../models/progress_info.dart';
 import '../models/queue_item.dart';
 import '../services/audio_compatibility_service.dart';
+import '../services/overwrite_behavior_service.dart';
 import '../services/preset_service.dart';
 import '../viewmodels/main_viewmodel.dart';
 import '../services/disc_detector.dart';
@@ -787,15 +788,30 @@ class MainWindow extends StatelessWidget {
     MainViewModel viewModel,
   ) async {
     // Check for existing output files that would be overwritten
-    final existingFiles = await _getExistingOutputFiles(viewModel.queue);
-    if (existingFiles.isNotEmpty) {
-      if (!context.mounted) return;
-      final shouldOverwrite = await OverwriteWarningDialog.show(
-        context: context,
-        existingFiles: existingFiles,
-      );
-      if (!shouldOverwrite) {
-        return; // User cancelled
+    final conflictingItems = await _getConflictingItems(viewModel.queue);
+    if (conflictingItems.isNotEmpty) {
+      switch (OverwriteBehaviorService.instance.behavior) {
+        case OverwriteBehavior.overwrite:
+          // Proceed silently - the existing files will be replaced.
+          break;
+        case OverwriteBehavior.rename:
+          // Give each conflicting item a fresh, non-colliding output path
+          // instead of touching what's already there.
+          for (final item in conflictingItems) {
+            item.outputPath = await OverwriteBehaviorService.instance
+                .uniquePath(item.outputPath);
+          }
+          viewModel.notifyOutputPathsChanged();
+          break;
+        case OverwriteBehavior.ask:
+          if (!context.mounted) return;
+          final shouldOverwrite = await OverwriteWarningDialog.show(
+            context: context,
+            existingFiles: conflictingItems.map((i) => i.outputPath).toList(),
+          );
+          if (!shouldOverwrite) {
+            return; // User cancelled
+          }
       }
     }
 
@@ -865,17 +881,18 @@ class MainWindow extends StatelessWidget {
     viewModel.startProcessing();
   }
 
-  /// Returns list of output file paths that already exist.
-  Future<List<String>> _getExistingOutputFiles(List<QueueItem> queue) async {
-    final existingFiles = <String>[];
+  /// Returns queue items (from those that will be processed) whose output
+  /// file already exists on disk.
+  Future<List<QueueItem>> _getConflictingItems(List<QueueItem> queue) async {
+    final conflicting = <QueueItem>[];
     for (final item in queue) {
       // Check items that will be processed (ready, failed, completed, cancelled)
       if (item.canProcess || item.canReprocess) {
         if (await File(item.outputPath).exists()) {
-          existingFiles.add(item.outputPath);
+          conflicting.add(item);
         }
       }
     }
-    return existingFiles;
+    return conflicting;
   }
 }
diff --git a/app/lib/views/overwrite_warning_dialog.dart b/app/lib/views/overwrite_warning_dialog.dart
index 9fa35d3..aa5f6e4 100644
--- a/app/lib/views/overwrite_warning_dialog.dart
+++ b/app/lib/views/overwrite_warning_dialog.dart
@@ -109,6 +109,14 @@ class OverwriteWarningDialog extends StatelessWidget {
                 },
               ),
             ),
+            const SizedBox(height: 12),
+            Text(
+              'You can change this behavior in Settings → General → '
+              'Existing Output Files.',
+              style: theme.textTheme.bodySmall?.copyWith(
+                color: theme.colorScheme.onSurfaceVariant,
+              ),
+            ),
           ],
         ),
       ),
diff --git a/app/lib/views/settings/settings_dialog.dart b/app/lib/views/settings/settings_dialog.dart
index 292489e..734dd29 100644
--- a/app/lib/views/settings/settings_dialog.dart
+++ b/app/lib/views/settings/settings_dialog.dart
@@ -12,6 +12,7 @@ import '../../models/video_job.dart';
 import '../../services/advanced_mode_service.dart';
 import '../../services/dependency_manager.dart';
 import '../../services/hardware_encoder_detector.dart';
+import '../../services/overwrite_behavior_service.dart';
 import '../../services/temp_directory_service.dart';
 import '../../services/update_checker.dart';
 import '../../utils/pixel_format.dart';
@@ -1748,13 +1749,26 @@ class _GeneralSettingsTabState extends State<_GeneralSettingsTab> {
   /// [TempDirectoryService] so the row repaints as soon as it's changed.
   String? _tempOverride;
 
+  /// Mirrors [OverwriteBehaviorService] so the row repaints as soon as it's
+  /// changed.
+  OverwriteBehavior _overwriteBehavior = OverwriteBehavior.ask;
+
   @override
   void initState() {
     super.initState();
     _tempOverride = TempDirectoryService.instance.override;
+    _overwriteBehavior = OverwriteBehaviorService.instance.behavior;
     _loadSettings();
   }
 
+  Future<void> _setOverwriteBehavior(OverwriteBehavior? value) async {
+    if (value == null) return;
+    await OverwriteBehaviorService.instance.setBehavior(value);
+    if (mounted) {
+      setState(() => _overwriteBehavior = value);
+    }
+  }
+
   /// Pick a directory for scratch files.
   Future<void> _selectTempDirectory() async {
     final result = await FilePicker.platform.getDirectoryPath(
@@ -1902,6 +1916,38 @@ class _GeneralSettingsTabState extends State<_GeneralSettingsTab> {
 
         const SizedBox(height: 24),
 
+        _buildSection(
+          context,
+          title: 'Existing Output Files',
+          child: Column(
+            crossAxisAlignment: CrossAxisAlignment.start,
+            children: [
+              for (final behavior in OverwriteBehavior.values)
+                RadioListTile<OverwriteBehavior>(
+                  contentPadding: EdgeInsets.zero,
+                  dense: true,
+                  title: Text(behavior.label),
+                  subtitle: Text(behavior.description),
+                  value: behavior,
+                  groupValue: _overwriteBehavior,
+                  onChanged: _setOverwriteBehavior,
+                ),
+              const SizedBox(height: 4),
+              Text(
+                'What to do when a job\'s output file already exists on disk.',
+                style: Theme.of(context).textTheme.bodySmall?.copyWith(
+                      color: Theme.of(context)
+                          .colorScheme
+                          .onSurface
+                          .withValues(alpha: 0.6),
+                    ),
+              ),
+            ],
+          ),
+        ),
+
+        const SizedBox(height: 24),
+
         _buildSection(
           context,
           title: 'About & Feedback',