diff --git a/MaddoShared.Tests/DataModelCharacterizationTests.cs b/MaddoShared.Tests/DataModelCharacterizationTests.cs
index 0a94ae9..ac09cb8 100644
--- a/MaddoShared.Tests/DataModelCharacterizationTests.cs
+++ b/MaddoShared.Tests/DataModelCharacterizationTests.cs
@@ -96,6 +96,45 @@ public class DataModelCharacterizationTests
         model.DestinationPath.ShouldBe($"C:{System.IO.Path.DirectorySeparatorChar}output{System.IO.Path.DirectorySeparatorChar}");
     }
 
+    [TestMethod]
+    public void DestinationPathChange_UpdatesAiCsvFileNameToMatchFinalFolderSegment()
+    {
+        var model = CreateModel();
+        model.CsvOutputPath = @"K:\various\catalogtest\aioutput\test2.csv";
+
+        model.DestinationPath = @"K:\various\catalogtest\Dest\03.KM_8_A\";
+
+        model.CsvOutputPath.ShouldBe(@"K:\various\catalogtest\aioutput\03.KM_8_A.csv");
+    }
+
+    [TestMethod]
+    public async Task ConfirmAiCsvOverwriteIfNeededAsync_CanCancelWhenCsvAlreadyExists()
+    {
+        using var tempDirectory = new TemporaryDirectory();
+        var csvPath = Path.Combine(tempDirectory.Path, "existing.csv");
+        File.WriteAllText(csvPath, "existing");
+
+        var model = CreateModel();
+        model.CsvOutputPath = csvPath;
+
+        string? requestedTitle = null;
+        string? requestedMessage = null;
+        model.ConfirmAiCsvOverwriteAsync = (title, message) =>
+        {
+            requestedTitle = title;
+            requestedMessage = message;
+            return Task.FromResult(false);
+        };
+
+        var shouldContinue = await model.ConfirmAiCsvOverwriteIfNeededAsync();
+
+        shouldContinue.ShouldBeFalse();
+        requestedTitle.ShouldBe("File CSV gia esistente");
+        requestedMessage.ShouldNotBeNull();
+        requestedMessage.ShouldContain("Vuoi sovrascriverlo?");
+        requestedMessage.ShouldContain(csvPath);
+    }
+
     [TestMethod]
     public void AiChildChange_RaisesDataModelPropertyChanged()
     {
diff --git a/imagecatalog/AvaloniaMainWindow.axaml.cs b/imagecatalog/AvaloniaMainWindow.axaml.cs
index d996708..6740d6f 100644
--- a/imagecatalog/AvaloniaMainWindow.axaml.cs
+++ b/imagecatalog/AvaloniaMainWindow.axaml.cs
@@ -41,6 +41,7 @@ public partial class AvaloniaMainWindow : Window
 
         // Let DataModel marshal callbacks onto Avalonia UI thread.
         _model.UiInvoker = action => Dispatcher.UIThread.Invoke(action);
+        _model.ConfirmAiCsvOverwriteAsync = ShowConfirmationDialogAsync;
 
         _model.SelectSourceFolderRequested += async (_, _) =>
         {
@@ -283,6 +284,25 @@ public partial class AvaloniaMainWindow : Window
         await dialog.ShowDialog(this);
     }
 
+    private async Task<bool> ShowConfirmationDialogAsync(string title, string message)
+    {
+        var dialog = new Window
+        {
+            Title = title,
+            Width = 520,
+            CanResize = false,
+            WindowStartupLocation = WindowStartupLocation.CenterOwner,
+            SizeToContent = SizeToContent.Height
+        };
+
+        dialog.Content = BuildConfirmationDialogContent(
+            message,
+            () => dialog.Close(true),
+            () => dialog.Close(false));
+
+        return await dialog.ShowDialog<bool>(this);
+    }
+
     private static Control BuildMessageDialogContent(string message, Action closeDialog)
     {
         var layout = new StackPanel
@@ -310,4 +330,46 @@ public partial class AvaloniaMainWindow : Window
         layout.Children.Add(closeButton);
         return layout;
     }
+
+    private static Control BuildConfirmationDialogContent(string message, Action confirmDialog, Action cancelDialog)
+    {
+        var layout = new StackPanel
+        {
+            Margin = new Thickness(16),
+            Spacing = 12
+        };
+
+        layout.Children.Add(new TextBlock
+        {
+            Text = message,
+            TextWrapping = Avalonia.Media.TextWrapping.Wrap,
+            MaxWidth = 460
+        });
+
+        var buttons = new StackPanel
+        {
+            Orientation = Orientation.Horizontal,
+            HorizontalAlignment = HorizontalAlignment.Right,
+            Spacing = 8
+        };
+
+        var cancelButton = new Button
+        {
+            Content = "Annulla",
+            MinWidth = 96
+        };
+        cancelButton.Click += (_, _) => cancelDialog();
+
+        var confirmButton = new Button
+        {
+            Content = "Sovrascrivi",
+            MinWidth = 96
+        };
+        confirmButton.Click += (_, _) => confirmDialog();
+
+        buttons.Children.Add(cancelButton);
+        buttons.Children.Add(confirmButton);
+        layout.Children.Add(buttons);
+        return layout;
+    }
 }
diff --git a/imagecatalog/DataModel.cs b/imagecatalog/DataModel.cs
index c89cb2c..d4a3dc4 100644
--- a/imagecatalog/DataModel.cs
+++ b/imagecatalog/DataModel.cs
@@ -22,6 +22,7 @@ using System.Text.RegularExpressions;
 using AutoMapper;
 using MaddoShared;
 using Microsoft.Extensions.Logging;
+using System.Collections.ObjectModel;
 
 namespace ImageCatalog_2
 {
@@ -82,6 +83,8 @@ namespace ImageCatalog_2
 
         private sealed record ParsedFaceMatcherRow(string PhotoId, double? Score, string RawRow, string DebugSummary);
 
+        private const string AiCsvOverwriteDialogTitle = "File CSV gia esistente";
+
         // ComboBox collections
         public List<string> AvailableFonts { get; }
         public List<string> VerticalPositions { get; } = new() { "Alto", "Centro", "Basso" };
@@ -145,6 +148,12 @@ namespace ImageCatalog_2
 
         private async Task StartAiAsync()
         {
+            if (!await ConfirmAiCsvOverwriteIfNeededAsync().ConfigureAwait(false))
+            {
+                await InvokeOnUiThreadAsync(() => NumberAiStatsSummary = "OCR annullato.").ConfigureAwait(false);
+                return;
+            }
+
             MainToken = new CancellationTokenSource();
             try
             {
@@ -267,6 +276,8 @@ namespace ImageCatalog_2
             set => _ai.CsvOutputPath = value;
         }
 
+        public Func<string, string, Task<bool>>? ConfirmAiCsvOverwriteAsync { get; set; }
+
         public bool UseNumberAiGpu
         {
             get => _ai.UseNumberAiGpu;
@@ -641,6 +652,11 @@ namespace ImageCatalog_2
                 return;
             }
 
+            if (string.Equals(e.PropertyName, nameof(PathSettingsViewModel.DestinationPath), StringComparison.Ordinal))
+            {
+                UpdateAiCsvOutputPathForDestination();
+            }
+
             NotifyPropertyChanged(e.PropertyName);
         }
 
@@ -2403,6 +2419,103 @@ namespace ImageCatalog_2
             });
         }
 
+        internal async Task<bool> ConfirmAiCsvOverwriteIfNeededAsync()
+        {
+            var csvOutputPath = NormalizeFilePathArgument(CsvOutputPath);
+            if (string.IsNullOrWhiteSpace(csvOutputPath) || !File.Exists(csvOutputPath))
+            {
+                return true;
+            }
+
+            var confirmOverwrite = ConfirmAiCsvOverwriteAsync;
+            if (confirmOverwrite is null)
+            {
+                return true;
+            }
+
+            var message = $"Il file CSV esiste gia:\n{csvOutputPath}\n\nVuoi sovrascriverlo? Se scegli Annulla l'operazione OCR non verra avviata.";
+            return await confirmOverwrite(AiCsvOverwriteDialogTitle, message).ConfigureAwait(false);
+        }
+
+        internal void UpdateAiCsvOutputPathForDestination()
+        {
+            var updatedPath = BuildAiCsvOutputPathForDestination(CsvOutputPath, DestinationPath);
+            if (string.Equals(updatedPath, CsvOutputPath, StringComparison.Ordinal))
+            {
+                return;
+            }
+
+            CsvOutputPath = updatedPath;
+        }
+
+        internal static string BuildAiCsvOutputPathForDestination(string currentCsvOutputPath, string destinationPath)
+        {
+            var normalizedCsvPath = NormalizeFilePathArgument(currentCsvOutputPath);
+            if (string.IsNullOrWhiteSpace(normalizedCsvPath))
+            {
+                return currentCsvOutputPath;
+            }
+
+            var directory = Path.GetDirectoryName(normalizedCsvPath);
+            var destinationFolderName = GetDestinationFolderName(destinationPath);
+            if (string.IsNullOrWhiteSpace(destinationFolderName))
+            {
+                return normalizedCsvPath;
+            }
+
+            var extension = Path.GetExtension(normalizedCsvPath);
+            if (string.IsNullOrWhiteSpace(extension))
+            {
+                extension = ".csv";
+            }
+
+            var safeFileName = SanitizeFileName(destinationFolderName) + extension;
+            return string.IsNullOrWhiteSpace(directory)
+                ? safeFileName
+                : Path.Combine(directory, safeFileName);
+        }
+
+        private static string GetDestinationFolderName(string destinationPath)
+        {
+            var normalizedDestinationPath = NormalizeDirectoryPathArgument(destinationPath);
+            if (string.IsNullOrWhiteSpace(normalizedDestinationPath))
+            {
+                return string.Empty;
+            }
+
+            var trimmedPath = normalizedDestinationPath.TrimEnd(Path.DirectorySeparatorChar, Path.AltDirectorySeparatorChar);
+            if (string.IsNullOrWhiteSpace(trimmedPath))
+            {
+                return string.Empty;
+            }
+
+            var rootPath = Path.GetPathRoot(trimmedPath)?.TrimEnd(Path.DirectorySeparatorChar, Path.AltDirectorySeparatorChar);
+            if (!string.IsNullOrWhiteSpace(rootPath)
+                && string.Equals(trimmedPath, rootPath, StringComparison.OrdinalIgnoreCase))
+            {
+                return string.Empty;
+            }
+
+            return Path.GetFileName(trimmedPath);
+        }
+
+        private static string SanitizeFileName(string value)
+        {
+            if (string.IsNullOrWhiteSpace(value))
+            {
+                return string.Empty;
+            }
+
+            var invalidFileNameChars = Path.GetInvalidFileNameChars();
+            var builder = new StringBuilder(value.Length);
+            foreach (var character in value)
+            {
+                builder.Append(Array.IndexOf(invalidFileNameChars, character) >= 0 ? '_' : character);
+            }
+
+            return builder.ToString();
+        }
+
         private void SetUseFaceGpu(bool value)
         {
             var currentValue = _ai.UseFaceGpu;