diff --git a/App/App.xaml.cs b/App/App.xaml.cs
index 5b82ced..06ab676 100644
--- a/App/App.xaml.cs
+++ b/App/App.xaml.cs
@@ -165,20 +165,22 @@ protected override void OnLaunched(LaunchActivatedEventArgs args)
         }, CancellationToken.None);
 
         // Initialize file sync.
-        var syncSessionCts = new CancellationTokenSource(TimeSpan.FromSeconds(10));
-        var syncSessionController = _services.GetRequiredService<ISyncSessionController>();
-        _ = syncSessionController.RefreshState(syncSessionCts.Token).ContinueWith(t =>
-        {
-            if (t.IsCanceled || t.Exception != null)
-            {
-                _logger.LogError(t.Exception, "failed to refresh sync state (canceled = {canceled})", t.IsCanceled);
-#if DEBUG
-                Debugger.Break();
-#endif
-            }
+        // We're adding a 5s delay here to avoid race conditions when loading the mutagen binary.
 
-            syncSessionCts.Dispose();
-        }, CancellationToken.None);
+        _ = Task.Delay(5000).ContinueWith((_) =>
+        {
+            var syncSessionCts = new CancellationTokenSource(TimeSpan.FromSeconds(10));
+            var syncSessionController = _services.GetRequiredService<ISyncSessionController>();
+            syncSessionController.RefreshState(syncSessionCts.Token).ContinueWith(
+                t =>
+                {
+                    if (t.IsCanceled || t.Exception != null)
+                    {
+                        _logger.LogError(t.Exception, "failed to refresh sync state (canceled = {canceled})", t.IsCanceled);
+                    }
+                    syncSessionCts.Dispose();
+                }, CancellationToken.None);
+        });
 
         // Prevent the TrayWindow from closing, just hide it.
         var trayWindow = _services.GetRequiredService<TrayWindow>();
diff --git a/App/Services/RpcController.cs b/App/Services/RpcController.cs
index 7beff66..7461ba8 100644
--- a/App/Services/RpcController.cs
+++ b/App/Services/RpcController.cs
@@ -313,7 +313,7 @@ private void SpeakerOnError(Exception e)
         Debug.WriteLine($"Error: {e}");
         try
         {
-            Reconnect(CancellationToken.None).Wait();
+            using var _ = Reconnect(CancellationToken.None);
         }
         catch
         {
diff --git a/App/ViewModels/FileSyncListViewModel.cs b/App/ViewModels/FileSyncListViewModel.cs
index 4777183..cb84f56 100644
--- a/App/ViewModels/FileSyncListViewModel.cs
+++ b/App/ViewModels/FileSyncListViewModel.cs
@@ -143,9 +143,9 @@ public void Initialize(Window window, DispatcherQueue dispatcherQueue)
 
         var rpcModel = _rpcController.GetState();
         var credentialModel = _credentialManager.GetCachedCredentials();
-        MaybeSetUnavailableMessage(rpcModel, credentialModel);
         var syncSessionState = _syncSessionController.GetState();
         UpdateSyncSessionState(syncSessionState);
+        MaybeSetUnavailableMessage(rpcModel, credentialModel, syncSessionState);
     }
 
     private void RpcControllerStateChanged(object? sender, RpcModel rpcModel)
@@ -159,7 +159,8 @@ private void RpcControllerStateChanged(object? sender, RpcModel rpcModel)
         }
 
         var credentialModel = _credentialManager.GetCachedCredentials();
-        MaybeSetUnavailableMessage(rpcModel, credentialModel);
+        var syncSessionState = _syncSessionController.GetState();
+        MaybeSetUnavailableMessage(rpcModel, credentialModel, syncSessionState);
     }
 
     private void CredentialManagerCredentialsChanged(object? sender, CredentialModel credentialModel)
@@ -173,7 +174,8 @@ private void CredentialManagerCredentialsChanged(object? sender, CredentialModel
         }
 
         var rpcModel = _rpcController.GetState();
-        MaybeSetUnavailableMessage(rpcModel, credentialModel);
+        var syncSessionState = _syncSessionController.GetState();
+        MaybeSetUnavailableMessage(rpcModel, credentialModel, syncSessionState);
     }
 
     private void SyncSessionStateChanged(object? sender, SyncSessionControllerStateModel syncSessionState)
@@ -189,7 +191,7 @@ private void SyncSessionStateChanged(object? sender, SyncSessionControllerStateM
         UpdateSyncSessionState(syncSessionState);
     }
 
-    private void MaybeSetUnavailableMessage(RpcModel rpcModel, CredentialModel credentialModel)
+    private void MaybeSetUnavailableMessage(RpcModel rpcModel, CredentialModel credentialModel, SyncSessionControllerStateModel syncSessionState)
     {
         var oldMessage = UnavailableMessage;
         if (rpcModel.RpcLifecycle != RpcLifecycle.Connected)
@@ -205,6 +207,10 @@ private void MaybeSetUnavailableMessage(RpcModel rpcModel, CredentialModel crede
         {
             UnavailableMessage = "Please start Coder Connect from the tray window to access file sync.";
         }
+        else if (syncSessionState.Lifecycle == SyncSessionControllerLifecycle.Uninitialized)
+        {
+            UnavailableMessage = "Sync session controller is not initialized. Please wait...";
+        }
         else
         {
             UnavailableMessage = null;
@@ -219,6 +225,13 @@ private void MaybeSetUnavailableMessage(RpcModel rpcModel, CredentialModel crede
 
     private void UpdateSyncSessionState(SyncSessionControllerStateModel syncSessionState)
     {
+        // This should never happen.
+        if (syncSessionState == null)
+            return;
+        if (syncSessionState.Lifecycle == SyncSessionControllerLifecycle.Uninitialized)
+        {
+            MaybeSetUnavailableMessage(_rpcController.GetState(), _credentialManager.GetCachedCredentials(), syncSessionState);
+        }
         Error = syncSessionState.DaemonError;
         Sessions = syncSessionState.SyncSessions.Select(s => new SyncSessionViewModel(this, s)).ToList();
     }
diff --git a/App/ViewModels/TrayWindowDisconnectedViewModel.cs b/App/ViewModels/TrayWindowDisconnectedViewModel.cs
index 5fe16a2..ce6582c 100644
--- a/App/ViewModels/TrayWindowDisconnectedViewModel.cs
+++ b/App/ViewModels/TrayWindowDisconnectedViewModel.cs
@@ -1,8 +1,9 @@
-using System.Threading.Tasks;
 using Coder.Desktop.App.Models;
 using Coder.Desktop.App.Services;
 using CommunityToolkit.Mvvm.ComponentModel;
 using CommunityToolkit.Mvvm.Input;
+using System;
+using System.Threading.Tasks;
 
 namespace Coder.Desktop.App.ViewModels;
 
@@ -11,6 +12,8 @@ public partial class TrayWindowDisconnectedViewModel : ObservableObject
     private readonly IRpcController _rpcController;
 
     [ObservableProperty] public partial bool ReconnectButtonEnabled { get; set; } = true;
+    [ObservableProperty] public partial string ErrorMessage { get; set; } = string.Empty;
+    [ObservableProperty] public partial bool ReconnectFailed { get; set; } = false;
 
     public TrayWindowDisconnectedViewModel(IRpcController rpcController)
     {
@@ -26,6 +29,16 @@ private void UpdateFromRpcModel(RpcModel rpcModel)
     [RelayCommand]
     public async Task Reconnect()
     {
-        await _rpcController.Reconnect();
+        try
+        {
+            ReconnectFailed = false;
+            ErrorMessage = string.Empty;
+            await _rpcController.Reconnect();
+        }
+        catch (Exception ex)
+        {
+            ErrorMessage = ex.Message;
+            ReconnectFailed = true;
+        }
     }
 }
diff --git a/App/Views/Pages/TrayWindowDisconnectedPage.xaml b/App/Views/Pages/TrayWindowDisconnectedPage.xaml
index 6675f8d..936c65f 100644
--- a/App/Views/Pages/TrayWindowDisconnectedPage.xaml
+++ b/App/Views/Pages/TrayWindowDisconnectedPage.xaml
@@ -30,6 +30,19 @@
 
         <controls:HorizontalRule />
 
+        <TextBlock FontWeight="semibold"
+                   TextWrapping="Wrap"
+                   Foreground="Red"
+                   Visibility="{x:Bind ViewModel.ReconnectFailed, Converter={StaticResource BoolToVisibilityConverter}, Mode=OneWay}"
+                   Text="Reconnect failed"/>
+
+        <TextBlock
+            TextWrapping="Wrap"
+            Margin="0,0,0,10"
+            Foreground="Red"
+            Visibility="{x:Bind ViewModel.ReconnectFailed, Converter={StaticResource BoolToVisibilityConverter}, Mode=OneWay}"
+            Text="{x:Bind ViewModel.ErrorMessage, Mode=OneWay}" />
+
         <HyperlinkButton
             HorizontalContentAlignment="Left"
             HorizontalAlignment="Stretch"
diff --git a/App/Views/TrayWindow.xaml.cs b/App/Views/TrayWindow.xaml.cs
index ef55095..7ecd75c 100644
--- a/App/Views/TrayWindow.xaml.cs
+++ b/App/Views/TrayWindow.xaml.cs
@@ -122,8 +122,7 @@ public TrayWindow(IRpcController rpcController, ICredentialManager credentialMan
     private void SetPageByState(RpcModel rpcModel, CredentialModel credentialModel,
         SyncSessionControllerStateModel syncSessionModel)
     {
-        if (credentialModel.State == CredentialState.Unknown ||
-            syncSessionModel.Lifecycle == SyncSessionControllerLifecycle.Uninitialized)
+        if (credentialModel.State == CredentialState.Unknown)
         {
             SetRootFrame(_loadingPage);
             return;