diff --git a/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs b/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
index 09ab2691..8573f4b6 100644
--- a/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
+++ b/DiscordChatExporter.Cli/Commands/Base/ExportCommandBase.cs
@@ -114,6 +114,12 @@ public abstract class ExportCommandBase : DiscordCommandBase
         init => field = value is not null ? Path.GetFullPath(value) : null;
     }
 
+    [CommandOption(
+        "prev-export",
+        Description = "What the exporter should do if the channel had already been exported."
+    )]
+    public FileExistsHandling FileExistsHandling { get; init; } = FileExistsHandling.Abort;
+
     [Obsolete("This option doesn't do anything. Kept for backwards compatibility.")]
     [CommandOption(
         "dateformat",
@@ -265,6 +271,7 @@ public abstract class ExportCommandBase : DiscordCommandBase
                                         ExportFormat,
                                         After,
                                         Before,
+                                        FileExistsHandling,
                                         PartitionLimit,
                                         MessageFilter,
                                         ShouldFormatMarkdown,
diff --git a/DiscordChatExporter.Core/Exporting/ChannelExporter.cs b/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
index b5ef7bc0..6a307970 100644
--- a/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
+++ b/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
@@ -32,10 +32,8 @@ public class ChannelExporter(DiscordClient discord)
         // TODO: Maybe add a way to search for old files after a username change
         if (File.Exists(request.OutputFilePath))
         {
-            // TODO: Add a way for the user to choose the setting
-            var choice = FileExistsHandling.Abort;
-
-            switch (choice)
+            // TODO: Maybe add an "Ask" option in the future
+            switch (request.FileExistsHandling)
             {
                 case FileExistsHandling.Abort:
                     Console.WriteLine("Channel aborted");
@@ -69,7 +67,7 @@ public class ChannelExporter(DiscordClient discord)
                     break;
                 default:
                     throw new InvalidOperationException(
-                        $"Unknown FileExistsHandling value '{choice}'."
+                        $"Unknown FileExistsHandling value '{request.FileExistsHandling}'."
                     );
             }
         }
diff --git a/DiscordChatExporter.Core/Exporting/ExportRequest.cs b/DiscordChatExporter.Core/Exporting/ExportRequest.cs
index 7ba9b4e2..d3dcba70 100644
--- a/DiscordChatExporter.Core/Exporting/ExportRequest.cs
+++ b/DiscordChatExporter.Core/Exporting/ExportRequest.cs
@@ -30,6 +30,8 @@ public partial class ExportRequest
 
     public Snowflake? Before { get; }
 
+    public FileExistsHandling FileExistsHandling { get; }
+
     public Snowflake? LastPriorMessage { get; set; }
 
     public PartitionLimit PartitionLimit { get; }
@@ -56,6 +58,7 @@ public partial class ExportRequest
         ExportFormat format,
         Snowflake? after,
         Snowflake? before,
+        FileExistsHandling fileExistsHandling,
         PartitionLimit partitionLimit,
         MessageFilter messageFilter,
         bool shouldFormatMarkdown,
@@ -70,6 +73,7 @@ public partial class ExportRequest
         Format = format;
         After = after;
         Before = before;
+        FileExistsHandling = fileExistsHandling;
         PartitionLimit = partitionLimit;
         MessageFilter = messageFilter;
         ShouldFormatMarkdown = shouldFormatMarkdown;
diff --git a/DiscordChatExporter.Gui/Services/SettingsService.cs b/DiscordChatExporter.Gui/Services/SettingsService.cs
index 87fb914b..c1a618d0 100644
--- a/DiscordChatExporter.Gui/Services/SettingsService.cs
+++ b/DiscordChatExporter.Gui/Services/SettingsService.cs
@@ -36,6 +36,9 @@ public partial class SettingsService()
     [ObservableProperty]
     public partial ThreadInclusionMode ThreadInclusionMode { get; set; }
 
+    [ObservableProperty]
+    public partial FileExistsHandling FileExistsHandling { get; set; }
+
     [ObservableProperty]
     public partial string? Locale { get; set; }
 
diff --git a/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs b/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
index a03d62d8..f5ead982 100644
--- a/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
+++ b/DiscordChatExporter.Gui/ViewModels/Components/DashboardViewModel.cs
@@ -270,6 +270,7 @@ public partial class DashboardViewModel : ViewModelBase
                             dialog.SelectedFormat,
                             dialog.After?.Pipe(timestamp => Snowflake.FromDate(timestamp, true)),
                             dialog.Before?.Pipe(timestamp => Snowflake.FromDate(timestamp)),
+                            _settingsService.FileExistsHandling,
                             dialog.PartitionLimit,
                             dialog.MessageFilter,
                             dialog.ShouldFormatMarkdown,
diff --git a/DiscordChatExporter.Gui/ViewModels/Dialogs/SettingsViewModel.cs b/DiscordChatExporter.Gui/ViewModels/Dialogs/SettingsViewModel.cs
index d3eaad9f..c9dd1e61 100644
--- a/DiscordChatExporter.Gui/ViewModels/Dialogs/SettingsViewModel.cs
+++ b/DiscordChatExporter.Gui/ViewModels/Dialogs/SettingsViewModel.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using DiscordChatExporter.Core.Discord;
+using DiscordChatExporter.Core.Exporting;
 using DiscordChatExporter.Core.Utils.Extensions;
 using DiscordChatExporter.Gui.Framework;
 using DiscordChatExporter.Gui.Models;
@@ -61,6 +62,15 @@ public class SettingsViewModel : DialogViewModelBase
         set => _settingsService.ThreadInclusionMode = value;
     }
 
+    public IReadOnlyList<FileExistsHandling> AvailableFileExistHandlingOptions { get; } =
+        Enum.GetValues<FileExistsHandling>();
+
+    public FileExistsHandling FileExistsHandling
+    {
+        get => _settingsService.FileExistsHandling;
+        set => _settingsService.FileExistsHandling = value;
+    }
+
     // These items have to be non-nullable because Avalonia ComboBox doesn't allow a null value to be selected
     public IReadOnlyList<string> AvailableLocales { get; } =
     [
diff --git a/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.axaml b/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.axaml
index a7a3c554..adce95e2 100644
--- a/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.axaml
+++ b/DiscordChatExporter.Gui/Views/Dialogs/SettingsView.axaml
@@ -131,6 +131,19 @@
                                 Value="{Binding ParallelLimit}" />
                         </StackPanel>
                     </DockPanel>
+
+                    <!--  File Exists Handling  -->
+                    <DockPanel
+                        Margin="16,8"
+                        LastChildFill="False"
+                        ToolTip.Tip="What the exporter should do if the channel had already been exported">
+                        <TextBlock DockPanel.Dock="Left" Text="Previous Export" />
+                        <ComboBox
+                            Width="150"
+                            DockPanel.Dock="Right"
+                            ItemsSource="{Binding AvailableFileExistHandlingOptions}"
+                            SelectedItem="{Binding FileExistsHandling}" />
+                    </DockPanel>
                 </StackPanel>
             </ScrollViewer>
         </Border>