diff --git a/PolyPilot.Tests/PolyPilot.Tests.csproj b/PolyPilot.Tests/PolyPilot.Tests.csproj
index 3c21127246..9897419368 100644
--- a/PolyPilot.Tests/PolyPilot.Tests.csproj
+++ b/PolyPilot.Tests/PolyPilot.Tests.csproj
@@ -39,6 +39,7 @@
     <Compile Include="../PolyPilot/Services/NotificationMessageBuilder.cs" Link="Shared/NotificationMessageBuilder.cs" />
     <Compile Include="../PolyPilot/Services/IChatDatabase.cs" Link="Shared/IChatDatabase.cs" />
     <Compile Include="../PolyPilot/Services/IServerManager.cs" Link="Shared/IServerManager.cs" />
+    <Compile Include="../PolyPilot/Services/ServerManager.cs" Link="Shared/ServerManager.cs" />
     <Compile Include="../PolyPilot/Services/IWsBridgeClient.cs" Link="Shared/IWsBridgeClient.cs" />
     <Compile Include="../PolyPilot/Services/IDemoService.cs" Link="Shared/IDemoService.cs" />
     <Compile Include="../PolyPilot/Services/INotificationManagerService.cs" Link="Shared/INotificationManagerService.cs" />
diff --git a/PolyPilot.Tests/ServerManagerTests.cs b/PolyPilot.Tests/ServerManagerTests.cs
new file mode 100644
index 0000000000..61bf174a17
--- /dev/null
+++ b/PolyPilot.Tests/ServerManagerTests.cs
@@ -0,0 +1,90 @@
+using System.Net;
+using System.Net.Sockets;
+using PolyPilot.Services;
+
+namespace PolyPilot.Tests;
+
+/// <summary>
+/// Tests for ServerManager.CheckServerRunning to verify socket exceptions
+/// are properly observed and don't cause UnobservedTaskException crashes.
+/// </summary>
+public class ServerManagerTests
+{
+    [Fact]
+    public void CheckServerRunning_ReturnsFalse_WhenNoServerListening()
+    {
+        var manager = new ServerManager();
+        // Port 19999 should not have a listener in test environment
+        var result = manager.CheckServerRunning("localhost", 19999);
+        Assert.False(result);
+    }
+
+    [Fact]
+    public void CheckServerRunning_ReturnsTrue_WhenServerListening()
+    {
+        // Start a temporary TCP listener
+        using var listener = new TcpListener(IPAddress.Loopback, 0);
+        listener.Start();
+        var port = ((IPEndPoint)listener.LocalEndpoint).Port;
+
+        var manager = new ServerManager();
+        var result = manager.CheckServerRunning("localhost", port);
+
+        Assert.True(result);
+        listener.Stop();
+    }
+
+    [Fact]
+    public void CheckServerRunning_NoUnobservedTaskException_OnConnectionRefused()
+    {
+        // Verify the fix: CheckServerRunning on a non-listening port must NOT leave
+        // unobserved Task exceptions that fire TaskScheduler.UnobservedTaskException.
+        using var unobservedSignal = new ManualResetEventSlim(false);
+        Exception? unobservedException = null;
+        EventHandler<UnobservedTaskExceptionEventArgs> handler = (sender, args) =>
+        {
+            if (args.Exception?.InnerException is SocketException)
+            {
+                unobservedException = args.Exception;
+                unobservedSignal.Set();
+            }
+        };
+
+        TaskScheduler.UnobservedTaskException += handler;
+        try
+        {
+            var manager = new ServerManager();
+            for (int i = 0; i < 5; i++)
+            {
+                manager.CheckServerRunning("localhost", 19999);
+            }
+
+            // Force GC to finalize any abandoned Tasks
+            GC.Collect();
+            GC.WaitForPendingFinalizers();
+            GC.Collect();
+
+            // If any unobserved Task exception exists, the finalizer will signal within the window.
+            // With the fix in place, no such tasks are left and the signal stays unset.
+            unobservedSignal.Wait(TimeSpan.FromMilliseconds(500));
+            Assert.Null(unobservedException);
+        }
+        finally
+        {
+            TaskScheduler.UnobservedTaskException -= handler;
+        }
+    }
+
+    [Fact]
+    public void CheckServerRunning_DefaultPort_UsesServerPort()
+    {
+        var manager = new ServerManager();
+        // The no-arg overload should use ServerPort (4321). We can't predict the result
+        // (persistent server may or may not be running), but we verify it doesn't throw
+        // and returns a valid result, then confirm the explicit-port overload also works.
+        var defaultResult = manager.CheckServerRunning();
+        var customResult = manager.CheckServerRunning("localhost", 19998);
+        Assert.True(defaultResult || !defaultResult); // completed without throwing
+        Assert.False(customResult);
+    }
+}
diff --git a/PolyPilot/Services/ServerManager.cs b/PolyPilot/Services/ServerManager.cs
index dcaf7df443..d951154cd7 100644
--- a/PolyPilot/Services/ServerManager.cs
+++ b/PolyPilot/Services/ServerManager.cs
@@ -35,14 +35,9 @@ public bool CheckServerRunning(string host = "localhost", int? port = null)
         try
         {
             using var client = new TcpClient();
-            var result = client.BeginConnect(host, port.Value, null, null);
-            var success = result.AsyncWaitHandle.WaitOne(TimeSpan.FromSeconds(1));
-            if (success && client.Connected)
-            {
-                client.EndConnect(result);
-                return true;
-            }
-            return false;
+            using var cts = new CancellationTokenSource(TimeSpan.FromSeconds(1));
+            client.ConnectAsync(host, port.Value, cts.Token).AsTask().GetAwaiter().GetResult();
+            return true;
         }
         catch
         {
diff --git a/PolyPilot/Services/WsBridgeClient.cs b/PolyPilot/Services/WsBridgeClient.cs
index c5739c2e4e..d484580e8f 100644
--- a/PolyPilot/Services/WsBridgeClient.cs
+++ b/PolyPilot/Services/WsBridgeClient.cs
@@ -122,6 +122,8 @@ public async Task ConnectAsync(string wsUrl, string? authToken = null, Cancellat
         if (completed == timeoutTask)
         {
             Console.WriteLine($"[WsBridgeClient] Connection timed out after 15s!");
+            // Observe the abandoned connectTask's exception to prevent UnobservedTaskException
+            _ = connectTask.ContinueWith(static t => { _ = t.Exception; }, CancellationToken.None, TaskContinuationOptions.OnlyOnFaulted, TaskScheduler.Default);
             invoker?.Dispose();
             _ws.Dispose();
             _ws = new ClientWebSocket();