diff --git a/src/Files.App/App.xaml.cs b/src/Files.App/App.xaml.cs
index ce8f7b3798de..f9202c20997b 100644
--- a/src/Files.App/App.xaml.cs
+++ b/src/Files.App/App.xaml.cs
@@ -226,6 +226,7 @@ await Task.WhenAll(
 			var updateService = Ioc.Default.GetRequiredService<IUpdateService>();
 			await updateService.CheckForUpdates();
 			await updateService.DownloadMandatoryUpdates();
+			await updateService.CheckAndUpdateFilesLauncherAsync();
 			await updateService.CheckLatestReleaseNotesAsync();
 
 			static async Task OptionalTask(Task task, bool condition)
diff --git a/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe b/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe
index 4f47b29ea154..3f2779c07963 100644
Binary files a/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe and b/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe differ
diff --git a/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe.sha256 b/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe.sha256
new file mode 100644
index 000000000000..55822f24124e
--- /dev/null
+++ b/src/Files.App/Assets/FilesOpenDialog/FilesLauncher.exe.sha256
@@ -0,0 +1 @@
+126534c53b4865d8b71d9378ce8d7071ff6dd71a58a0773345867dcfb80952a7
diff --git a/src/Files.App/ServicesImplementation/SideloadUpdateService.cs b/src/Files.App/ServicesImplementation/SideloadUpdateService.cs
index 5d3b55d154ee..2305205b62fd 100644
--- a/src/Files.App/ServicesImplementation/SideloadUpdateService.cs
+++ b/src/Files.App/ServicesImplementation/SideloadUpdateService.cs
@@ -153,6 +153,49 @@ public async Task CheckForUpdates()
 			}
 		}
 
+		public async Task CheckAndUpdateFilesLauncherAsync()
+		{
+			var destFolderPath = Path.Combine(UserDataPaths.GetDefault().LocalAppData, "Files");
+			var destExeFilePath = Path.Combine(destFolderPath, "FilesLauncher.exe");
+
+			if (Path.Exists(destExeFilePath))
+			{
+				var hashEqual = false;
+				var srcHashFile = await StorageFile.GetFileFromApplicationUriAsync(new Uri("ms-appx:///Assets/FilesOpenDialog/FilesLauncher.exe.sha256"));
+				var destHashFilePath = Path.Combine(destFolderPath, "FilesLauncher.exe.sha256");
+
+				if (Path.Exists(destHashFilePath))
+				{
+					using var srcStream = (await srcHashFile.OpenReadAsync()).AsStream();
+					using var destStream = File.OpenRead(destHashFilePath);
+
+					hashEqual = HashEqual(srcStream, destStream);
+				}
+
+				if (!hashEqual)
+				{
+					var srcExeFile = await StorageFile.GetFileFromApplicationUriAsync(new Uri("ms-appx:///Assets/FilesOpenDialog/FilesLauncher.exe"));
+					var destFolder = await StorageFolder.GetFolderFromPathAsync(destFolderPath);
+
+					await srcExeFile.CopyAsync(destFolder, "FilesLauncher.exe", NameCollisionOption.ReplaceExisting);
+					await srcHashFile.CopyAsync(destFolder, "FilesLauncher.exe.sha256", NameCollisionOption.ReplaceExisting);
+
+					App.Logger.Info("FilesLauncher updated.");
+				}
+			}
+
+			bool HashEqual(Stream a, Stream b)
+			{
+				Span<byte> bufferA = stackalloc byte[64];
+				Span<byte> bufferB = stackalloc byte[64];
+
+				a.Read(bufferA);
+				b.Read(bufferB);
+
+				return bufferA.SequenceEqual(bufferB);
+			}
+		}
+
 		private async Task StartBackgroundDownload()
 		{
 			try
diff --git a/src/Files.App/ServicesImplementation/UpdateService.cs b/src/Files.App/ServicesImplementation/UpdateService.cs
index 88f7b4823e93..228a470a28d1 100644
--- a/src/Files.App/ServicesImplementation/UpdateService.cs
+++ b/src/Files.App/ServicesImplementation/UpdateService.cs
@@ -11,6 +11,7 @@
 using System.Threading;
 using System.Threading.Tasks;
 using Windows.Services.Store;
+using Windows.Storage;
 using WinRT.Interop;
 
 namespace Files.App.ServicesImplementation
@@ -178,6 +179,49 @@ public async Task CheckLatestReleaseNotesAsync(CancellationToken cancellationTok
 			}
 		}
 
+		public async Task CheckAndUpdateFilesLauncherAsync()
+		{
+			var destFolderPath = Path.Combine(UserDataPaths.GetDefault().LocalAppData, "Files");
+			var destExeFilePath = Path.Combine(destFolderPath, "FilesLauncher.exe");
+
+			if (Path.Exists(destExeFilePath))
+			{
+				var hashEqual = false;
+				var srcHashFile = await StorageFile.GetFileFromApplicationUriAsync(new Uri("ms-appx:///Assets/FilesOpenDialog/FilesLauncher.exe.sha256"));
+				var destHashFilePath = Path.Combine(destFolderPath, "FilesLauncher.exe.sha256");
+
+				if (Path.Exists(destHashFilePath))
+				{
+					using var srcStream = (await srcHashFile.OpenReadAsync()).AsStream();
+					using var destStream = File.OpenRead(destHashFilePath);
+
+					hashEqual = HashEqual(srcStream, destStream);
+				}
+
+				if (!hashEqual)
+				{
+					var srcExeFile = await StorageFile.GetFileFromApplicationUriAsync(new Uri("ms-appx:///Assets/FilesOpenDialog/FilesLauncher.exe"));
+					var destFolder = await StorageFolder.GetFolderFromPathAsync(destFolderPath);
+
+					await srcExeFile.CopyAsync(destFolder, "FilesLauncher.exe", NameCollisionOption.ReplaceExisting);
+					await srcHashFile.CopyAsync(destFolder, "FilesLauncher.exe.sha256", NameCollisionOption.ReplaceExisting);
+
+					App.Logger.Info("FilesLauncher updated.");
+				}
+			}
+
+			bool HashEqual(Stream a, Stream b)
+			{
+				Span<byte> bufferA = stackalloc byte[64];
+				Span<byte> bufferB = stackalloc byte[64];
+
+				a.Read(bufferA);
+				b.Read(bufferB);
+
+				return bufferA.SequenceEqual(bufferB);
+			}
+		}
+
 		// WINUI3
 		private static ContentDialog SetContentDialogRoot(ContentDialog contentDialog)
 		{
diff --git a/src/Files.Backend/Services/IUpdateService.cs b/src/Files.Backend/Services/IUpdateService.cs
index 9134da609831..ffe3ee708767 100644
--- a/src/Files.Backend/Services/IUpdateService.cs
+++ b/src/Files.Backend/Services/IUpdateService.cs
@@ -38,5 +38,10 @@ public interface IUpdateService : INotifyPropertyChanged
 		/// Gets release notes for the latest release
 		/// </summary>
 		Task<string?> GetLatestReleaseNotesAsync(CancellationToken cancellationToken = default);
+
+		/// <summary>
+		/// Replace FilesLauncher.exe if it is used and has been updated
+		/// </summary>
+		Task CheckAndUpdateFilesLauncherAsync();
 	}
 }
diff --git a/src/Files.OpenDialog/FilesLauncher/FilesLauncher.vcxproj b/src/Files.OpenDialog/FilesLauncher/FilesLauncher.vcxproj
index 042934654daf..8f6a74b9b772 100644
--- a/src/Files.OpenDialog/FilesLauncher/FilesLauncher.vcxproj
+++ b/src/Files.OpenDialog/FilesLauncher/FilesLauncher.vcxproj
@@ -189,7 +189,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|Win32'">
@@ -211,7 +212,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Sideload|Win32'">
@@ -233,7 +235,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|x64'">
@@ -251,7 +254,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|arm64'">
@@ -269,7 +273,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|x64'">
@@ -291,7 +296,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Sideload|x64'">
@@ -313,7 +319,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|arm64'">
@@ -335,7 +342,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Sideload|arm64'">
@@ -357,7 +365,8 @@
       <OutputFile>$(OutDir)FilesLauncher$(TargetExt)</OutputFile>
     </Link>
     <PostBuildEvent>
-      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"</Command>
+      <Command>xcopy /s /y "$(ProjectDir)$(OutDir)*.exe" "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog"
+certutil -hashfile "$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName)" SHA256|findstr /R /V "^SHA256 ^CertUtil"&gt;"$(ProjectDir)..\..\..\src\Files.App\Assets\FilesOpenDialog\$(TargetFileName).sha256"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemGroup>