diff --git a/DevDrive.csproj b/DevDrive.csproj
index b94b7ed..ce18578 100644
--- a/DevDrive.csproj
+++ b/DevDrive.csproj
@@ -3,6 +3,7 @@
   <PropertyGroup>
     <OutputType>WinExe</OutputType>
     <TargetFramework>net8.0-windows</TargetFramework>
+    <UseWindowsForms>true</UseWindowsForms>
     <ImplicitUsings>enable</ImplicitUsings>
     <Nullable>enable</Nullable>
     <PlatformTarget>x64</PlatformTarget>
diff --git a/DevDriveConfig.cs b/DevDriveConfig.cs
index f08a759..6fc0f11 100644
--- a/DevDriveConfig.cs
+++ b/DevDriveConfig.cs
@@ -36,6 +36,12 @@ public class DevDriveConfig
     /// </summary>
     [JsonPropertyName("paths")]
     public List<SymlinkEntry> Paths { get; set; } = [];
+
+    /// <summary>
+    /// List of applications to prompt for launch after mounting.
+    /// </summary>
+    [JsonPropertyName("startupApps")]
+    public List<StartupApp> StartupApps { get; set; } = [];
 }
 
 /// <summary>
@@ -55,3 +61,39 @@ public class SymlinkEntry
     [JsonPropertyName("path")]
     public string Path { get; set; } = string.Empty;
 }
+
+/// <summary>
+/// Represents an application to launch after mounting.
+/// </summary>
+public class StartupApp
+{
+    /// <summary>
+    /// Display name shown in the dialog.
+    /// </summary>
+    [JsonPropertyName("name")]
+    public string Name { get; set; } = string.Empty;
+
+    /// <summary>
+    /// Path to the executable.
+    /// </summary>
+    [JsonPropertyName("path")]
+    public string Path { get; set; } = string.Empty;
+
+    /// <summary>
+    /// Command line arguments (optional).
+    /// </summary>
+    [JsonPropertyName("arguments")]
+    public string Arguments { get; set; } = string.Empty;
+
+    /// <summary>
+    /// Working directory (optional, defaults to executable's directory).
+    /// </summary>
+    [JsonPropertyName("workingDirectory")]
+    public string WorkingDirectory { get; set; } = string.Empty;
+
+    /// <summary>
+    /// Whether this app is checked by default in the dialog.
+    /// </summary>
+    [JsonPropertyName("checkedByDefault")]
+    public bool CheckedByDefault { get; set; } = true;
+}
diff --git a/Program.cs b/Program.cs
index 6cb9a82..1b75839 100644
--- a/Program.cs
+++ b/Program.cs
@@ -301,6 +301,12 @@ public static class Program
                 MountDrive();
                 SyncSymlinksFromConfig(config);
                 _lastConfig = config;
+
+                if (config.StartupApps.Count > 0)
+                {
+                    var driveName = config.DriveName ?? "Dev Drive";
+                    Task.Run(() => StartupDialog.ShowIfNeeded(config.StartupApps, driveName));
+                }
             }
         }
     }
diff --git a/StartupDialog.cs b/StartupDialog.cs
new file mode 100644
index 0000000..6d92cd9
--- /dev/null
+++ b/StartupDialog.cs
@@ -0,0 +1,201 @@
+using System.Diagnostics;
+using System.Runtime.Versioning;
+
+namespace DevDrive;
+
+/// <summary>
+/// Dialog that prompts the user to select which startup apps to launch.
+/// </summary>
+[SupportedOSPlatform("windows")]
+public class StartupDialog : Form
+{
+    private readonly List<StartupApp> _apps;
+    private readonly List<CheckBox> _checkboxes = [];
+    private readonly Button _launchButton;
+    private readonly Button _cancelButton;
+
+    /// <summary>
+    /// Creates a new startup dialog for the given apps.
+    /// </summary>
+    /// <param name="apps">List of startup apps to display.</param>
+    /// <param name="driveName">Name of the drive for the title.</param>
+    public StartupDialog(List<StartupApp> apps, string driveName)
+    {
+        _apps = apps;
+
+        Text = $"{driveName} - Startup Apps";
+        FormBorderStyle = FormBorderStyle.FixedDialog;
+        StartPosition = FormStartPosition.CenterScreen;
+        MaximizeBox = false;
+        MinimizeBox = false;
+        AutoScaleMode = AutoScaleMode.Dpi;
+
+        var padding = 16;
+        var checkboxHeight = 28;
+        var buttonHeight = 32;
+        var buttonWidth = 100;
+
+        var contentHeight = padding + (_apps.Count * checkboxHeight) + padding + buttonHeight + padding;
+        var contentWidth = 350;
+
+        ClientSize = new Size(contentWidth, contentHeight);
+
+        var yPos = padding;
+
+        foreach (var app in _apps)
+        {
+            var checkbox = new CheckBox
+            {
+                Text = app.Name,
+                Tag = app,
+                Checked = app.CheckedByDefault,
+                Location = new Point(padding, yPos),
+                Size = new Size(contentWidth - (padding * 2), checkboxHeight),
+                Font = new Font("Segoe UI", 10)
+            };
+
+            _checkboxes.Add(checkbox);
+            Controls.Add(checkbox);
+            yPos += checkboxHeight;
+        }
+
+        yPos += padding;
+
+        _launchButton = new Button
+        {
+            Text = "Launch",
+            DialogResult = DialogResult.OK,
+            Location = new Point(contentWidth - padding - buttonWidth - 8 - buttonWidth, yPos),
+            Size = new Size(buttonWidth, buttonHeight),
+            Font = new Font("Segoe UI", 9)
+        };
+        _launchButton.Click += OnLaunchClick;
+        Controls.Add(_launchButton);
+
+        _cancelButton = new Button
+        {
+            Text = "Skip",
+            DialogResult = DialogResult.Cancel,
+            Location = new Point(contentWidth - padding - buttonWidth, yPos),
+            Size = new Size(buttonWidth, buttonHeight),
+            Font = new Font("Segoe UI", 9)
+        };
+        Controls.Add(_cancelButton);
+
+        AcceptButton = _launchButton;
+        CancelButton = _cancelButton;
+    }
+
+    private void OnLaunchClick(object? sender, EventArgs e)
+    {
+        LaunchSelectedApps();
+    }
+
+    /// <summary>
+    /// Launches all selected apps.
+    /// </summary>
+    private void LaunchSelectedApps()
+    {
+        foreach (var checkbox in _checkboxes)
+        {
+            if (!checkbox.Checked)
+            {
+                continue;
+            }
+
+            if (checkbox.Tag is not StartupApp app)
+            {
+                continue;
+            }
+
+            try
+            {
+                var startInfo = new ProcessStartInfo
+                {
+                    FileName = Environment.ExpandEnvironmentVariables(app.Path),
+                    UseShellExecute = true
+                };
+
+                if (!string.IsNullOrWhiteSpace(app.Arguments))
+                {
+                    startInfo.Arguments = Environment.ExpandEnvironmentVariables(app.Arguments);
+                }
+
+                if (!string.IsNullOrWhiteSpace(app.WorkingDirectory))
+                {
+                    startInfo.WorkingDirectory = Environment.ExpandEnvironmentVariables(app.WorkingDirectory);
+                }
+
+                Process.Start(startInfo);
+                Console.WriteLine($"[DevDrive] Launched: {app.Name}");
+            }
+            catch (Exception ex)
+            {
+                Console.WriteLine($"[DevDrive] Failed to launch {app.Name}: {ex.Message}");
+            }
+        }
+    }
+
+    /// <summary>
+    /// Shows the startup dialog if there are apps to display.
+    /// </summary>
+    /// <param name="apps">List of startup apps.</param>
+    /// <param name="driveName">Name of the drive.</param>
+    public static void ShowIfNeeded(List<StartupApp> apps, string driveName)
+    {
+        if (apps.Count == 0)
+        {
+            return;
+        }
+
+        if (apps.Count == 1)
+        {
+            var app = apps[0];
+            var result = MessageBox.Show(
+                $"Launch {app.Name}?",
+                $"{driveName} - Startup",
+                MessageBoxButtons.YesNo,
+                MessageBoxIcon.Question
+            );
+
+            if (result == DialogResult.Yes)
+            {
+                LaunchSingleApp(app);
+            }
+            return;
+        }
+
+        Application.EnableVisualStyles();
+        using var dialog = new StartupDialog(apps, driveName);
+        dialog.ShowDialog();
+    }
+
+    private static void LaunchSingleApp(StartupApp app)
+    {
+        try
+        {
+            var startInfo = new ProcessStartInfo
+            {
+                FileName = Environment.ExpandEnvironmentVariables(app.Path),
+                UseShellExecute = true
+            };
+
+            if (!string.IsNullOrWhiteSpace(app.Arguments))
+            {
+                startInfo.Arguments = Environment.ExpandEnvironmentVariables(app.Arguments);
+            }
+
+            if (!string.IsNullOrWhiteSpace(app.WorkingDirectory))
+            {
+                startInfo.WorkingDirectory = Environment.ExpandEnvironmentVariables(app.WorkingDirectory);
+            }
+
+            Process.Start(startInfo);
+            Console.WriteLine($"[DevDrive] Launched: {app.Name}");
+        }
+        catch (Exception ex)
+        {
+            Console.WriteLine($"[DevDrive] Failed to launch {app.Name}: {ex.Message}");
+        }
+    }
+}