diff --git a/Wino.Core.UWP/Services/WinoServerConnectionManager.cs b/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
index bb5fd965..3243373e 100644
--- a/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
+++ b/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
@@ -109,12 +109,12 @@ namespace Wino.Core.UWP.Services
             {
                 try
                 {
-                    ConnectingHandle ??= new TaskCompletionSource<bool>();
-
-                    var connectionCancellationToken = new CancellationTokenSource(TimeSpan.FromMilliseconds(ServerConnectionTimeoutMs));
+                    ConnectingHandle = new TaskCompletionSource<bool>();
 
                     Status = WinoServerConnectionStatus.Connecting;
 
+                    var connectionCancellationToken = new CancellationTokenSource(TimeSpan.FromMilliseconds(ServerConnectionTimeoutMs));
+
                     await FullTrustProcessLauncher.LaunchFullTrustProcessForCurrentAppAsync();
 
                     // Connection establishment handler is in App.xaml.cs OnBackgroundActivated.
@@ -125,6 +125,14 @@ namespace Wino.Core.UWP.Services
 
                     Log.Information("Server connection established successfully.");
                 }
+                catch (OperationCanceledException canceledException)
+                {
+                    Log.Error(canceledException, $"Server process did not start in {ServerConnectionTimeoutMs} ms. Operation is canceled.");
+
+                    ConnectingHandle?.TrySetException(canceledException);
+
+                    return false;
+                }
                 catch (Exception ex)
                 {
                     Log.Error(ex, "Failed to connect to the server.");