diff --git a/Wino.Core.Domain/Interfaces/IWinoServerConnectionManager.cs b/Wino.Core.Domain/Interfaces/IWinoServerConnectionManager.cs
index 4285f128..eff74b95 100644
--- a/Wino.Core.Domain/Interfaces/IWinoServerConnectionManager.cs
+++ b/Wino.Core.Domain/Interfaces/IWinoServerConnectionManager.cs
@@ -19,19 +19,13 @@ namespace Wino.Core.Domain.Interfaces
 
         /// <summary>
         /// Launches Full Trust process (Wino Server) and awaits connection completion.
-        /// If connection is not established in 5 seconds, it will return false.
+        /// If connection is not established in 10 seconds, it will return false.
         /// If the server process is already running, it'll connect to existing one.
         /// If the server process is not running, it'll be launched and connection establishment is awaited.
         /// </summary>
         /// <returns>Whether connection is established or not.</returns>
         Task<bool> ConnectAsync();
 
-        /// <summary>
-        /// Disconnects from existing connection and disposes the connection.
-        /// </summary>
-        /// <returns>Whether disconnection is succesfull or not.</returns>
-        Task<bool> DisconnectAsync();
-
         /// <summary>
         /// Queues a new user request to be processed by Wino Server.
         /// Healthy connection must present before calling this method.
@@ -48,6 +42,13 @@ namespace Wino.Core.Domain.Interfaces
         /// <param name="clientMessage">Request type.</param>
         /// <returns>Response received from the server for the given TResponse type.</returns>
         Task<WinoServerResponse<TResponse>> GetResponseAsync<TResponse, TRequestType>(TRequestType clientMessage) where TRequestType : IClientMessage;
+
+        /// <summary>
+        /// Handle for connecting to the server.
+        /// If the server is already running, it'll connect to existing one.
+        /// Callers can await this handle to wait for connection establishment.
+        /// </summary>
+        TaskCompletionSource<bool> ConnectingHandle { get; }
     }
 
     public interface IWinoServerConnectionManager<TAppServiceConnection> : IWinoServerConnectionManager, IInitializeAsync
diff --git a/Wino.Core.Domain/Models/Server/WinoServerResponse.cs b/Wino.Core.Domain/Models/Server/WinoServerResponse.cs
index 45b8bb06..d903aa6e 100644
--- a/Wino.Core.Domain/Models/Server/WinoServerResponse.cs
+++ b/Wino.Core.Domain/Models/Server/WinoServerResponse.cs
@@ -13,8 +13,6 @@ namespace Wino.Core.Domain.Models.Server
         public string Message { get; set; }
         public T Data { get; set; }
 
-        // protected WinoServerResponse() { }
-
         public static WinoServerResponse<T> CreateSuccessResponse(T data)
         {
             return new WinoServerResponse<T>
diff --git a/Wino.Core.UWP/Services/WinoServerConnectionManager.cs b/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
index 9aaca3ed..bb5fd965 100644
--- a/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
+++ b/Wino.Core.UWP/Services/WinoServerConnectionManager.cs
@@ -26,10 +26,11 @@ namespace Wino.Core.UWP.Services
         IWinoServerConnectionManager<AppServiceConnection>,
         IRecipient<WinoServerConnectionEstablished>
     {
-        private const int ServerConnectionTimeoutMs = 5000;
+        private const int ServerConnectionTimeoutMs = 10000;
 
         public event EventHandler<WinoServerConnectionStatus> StatusChanged;
-        private TaskCompletionSource<bool> _connectionTaskCompletionSource;
+
+        public TaskCompletionSource<bool> ConnectingHandle { get; private set; }
 
         private ILogger Logger => Logger.ForContext<WinoServerConnectionManager>();
 
@@ -40,6 +41,7 @@ namespace Wino.Core.UWP.Services
             get { return status; }
             private set
             {
+                Log.Information("Server connection status changed to {Status}.", value);
                 status = value;
                 StatusChanged?.Invoke(this, value);
             }
@@ -85,13 +87,29 @@ namespace Wino.Core.UWP.Services
 
         public async Task<bool> ConnectAsync()
         {
-            if (Status == WinoServerConnectionStatus.Connected) return true;
+            if (Status == WinoServerConnectionStatus.Connected)
+            {
+                Log.Information("Server is already connected.");
+                return true;
+            }
+
+            if (Status == WinoServerConnectionStatus.Connecting)
+            {
+                // A connection is already being established at the moment.
+                // No need to run another connection establishment process.
+                // Await the connecting handler if possible.
+
+                if (ConnectingHandle != null)
+                {
+                    return await ConnectingHandle.Task;
+                }
+            }
 
             if (ApiInformation.IsApiContractPresent("Windows.ApplicationModel.FullTrustAppContract", 1, 0))
             {
                 try
                 {
-                    _connectionTaskCompletionSource ??= new TaskCompletionSource<bool>();
+                    ConnectingHandle ??= new TaskCompletionSource<bool>();
 
                     var connectionCancellationToken = new CancellationTokenSource(TimeSpan.FromMilliseconds(ServerConnectionTimeoutMs));
 
@@ -103,34 +121,40 @@ namespace Wino.Core.UWP.Services
                     // Once the connection is established, the handler will set the Connection property
                     // and WinoServerConnectionEstablished will be fired by the messenger.
 
-                    await _connectionTaskCompletionSource.Task.WaitAsync(connectionCancellationToken.Token);
+                    await ConnectingHandle.Task.WaitAsync(connectionCancellationToken.Token);
+
+                    Log.Information("Server connection established successfully.");
                 }
-                catch (Exception)
+                catch (Exception ex)
                 {
+                    Log.Error(ex, "Failed to connect to the server.");
+
                     Status = WinoServerConnectionStatus.Failed;
                     return false;
                 }
 
                 return true;
             }
+            else
+            {
+                Log.Information("FullTrustAppContract is not present in the system. Server connection is not possible.");
+            }
 
             return false;
         }
 
-        public async Task<bool> DisconnectAsync()
-        {
-            if (Connection == null || Status == WinoServerConnectionStatus.Disconnected) return true;
-
-            // TODO: Send disconnect message to the fulltrust process.
-
-            return true;
-        }
-
         public async Task InitializeAsync()
         {
             var isConnectionSuccessfull = await ConnectAsync();
 
-            // TODO: Log connection status
+            if (isConnectionSuccessfull)
+            {
+                Log.Information("ServerConnectionManager initialized successfully.");
+            }
+            else
+            {
+                Log.Error("ServerConnectionManager initialization failed.");
+            }
         }
 
         private void ServerMessageReceived(AppServiceConnection sender, AppServiceRequestReceivedEventArgs args)
@@ -222,7 +246,7 @@ namespace Wino.Core.UWP.Services
 
         private void ServerDisconnected(AppServiceConnection sender, AppServiceClosedEventArgs args)
         {
-            // TODO: Handle server disconnection.
+            Log.Information("Server disconnected.");
         }
 
         public async Task QueueRequestAsync(IRequestBase request, Guid accountId)
@@ -242,8 +266,8 @@ namespace Wino.Core.UWP.Services
 
         private async Task<WinoServerResponse<TResponse>> GetResponseInternalAsync<TResponse, TRequestType>(TRequestType message, Dictionary<string, object> parameters = null)
         {
-            if (Connection == null)
-                return WinoServerResponse<TResponse>.CreateErrorResponse("Server connection is not established.");
+            if (Status != WinoServerConnectionStatus.Connected)
+                await ConnectAsync();
 
             string serializedMessage = string.Empty;
 
@@ -306,11 +330,6 @@ namespace Wino.Core.UWP.Services
         }
 
         public void Receive(WinoServerConnectionEstablished message)
-        {
-            if (_connectionTaskCompletionSource != null)
-            {
-                _connectionTaskCompletionSource.TrySetResult(true);
-            }
-        }
+            => ConnectingHandle?.TrySetResult(true);
     }
 }
diff --git a/Wino.Core/Services/WinoRequestDelegator.cs b/Wino.Core/Services/WinoRequestDelegator.cs
index b47196ba..c4e9b60e 100644
--- a/Wino.Core/Services/WinoRequestDelegator.cs
+++ b/Wino.Core/Services/WinoRequestDelegator.cs
@@ -80,7 +80,7 @@ namespace Wino.Core.Services
                     await QueueRequestAsync(accountRequest, accountId.Key);
                 }
 
-                QueueSynchronization(accountId.Key);
+                await QueueSynchronizationAsync(accountId.Key);
             }
         }
 
@@ -108,7 +108,7 @@ namespace Wino.Core.Services
             if (request == null) return;
 
             await QueueRequestAsync(request, accountId);
-            QueueSynchronization(accountId);
+            await QueueSynchronizationAsync(accountId);
         }
 
         public async Task ExecuteAsync(DraftPreparationRequest draftPreperationRequest)
@@ -116,7 +116,7 @@ namespace Wino.Core.Services
             var request = new CreateDraftRequest(draftPreperationRequest);
 
             await QueueRequestAsync(request, draftPreperationRequest.Account.Id);
-            QueueSynchronization(draftPreperationRequest.Account.Id);
+            await QueueSynchronizationAsync(draftPreperationRequest.Account.Id);
         }
 
         public async Task ExecuteAsync(SendDraftPreparationRequest sendDraftPreperationRequest)
@@ -124,23 +124,26 @@ namespace Wino.Core.Services
             var request = new SendDraftRequest(sendDraftPreperationRequest);
 
             await QueueRequestAsync(request, sendDraftPreperationRequest.MailItem.AssignedAccount.Id);
-            QueueSynchronization(sendDraftPreperationRequest.MailItem.AssignedAccount.Id);
+            await QueueSynchronizationAsync(sendDraftPreperationRequest.MailItem.AssignedAccount.Id);
         }
 
         private async Task QueueRequestAsync(IRequestBase request, Guid accountId)
         {
             try
             {
+                await EnsureServerConnectedAsync();
                 await _winoServerConnectionManager.QueueRequestAsync(request, accountId);
             }
             catch (WinoServerException serverException)
             {
-                _dialogService.InfoBarMessage("", serverException.Message, InfoBarMessageType.Error);
+                _dialogService.InfoBarMessage("Wino Server Exception", serverException.Message, InfoBarMessageType.Error);
             }
         }
 
-        private void QueueSynchronization(Guid accountId)
+        private async Task QueueSynchronizationAsync(Guid accountId)
         {
+            await EnsureServerConnectedAsync();
+
             var options = new SynchronizationOptions()
             {
                 AccountId = accountId,
@@ -149,5 +152,12 @@ namespace Wino.Core.Services
 
             WeakReferenceMessenger.Default.Send(new NewSynchronizationRequested(options, SynchronizationSource.Client));
         }
+
+        private async Task EnsureServerConnectedAsync()
+        {
+            if (_winoServerConnectionManager.Status == WinoServerConnectionStatus.Connected) return;
+
+            await _winoServerConnectionManager.ConnectAsync();
+        }
     }
 }
diff --git a/Wino.Mail.ViewModels/MailListPageViewModel.cs b/Wino.Mail.ViewModels/MailListPageViewModel.cs
index e3f24b1a..2470bec4 100644
--- a/Wino.Mail.ViewModels/MailListPageViewModel.cs
+++ b/Wino.Mail.ViewModels/MailListPageViewModel.cs
@@ -845,9 +845,6 @@ namespace Wino.Mail.ViewModels
             trackingSynchronizationId = null;
             completedTrackingSynchronizationCount = 0;
 
-            // Check whether the account synchronizer that this folder belongs to is already in synchronization.
-            await CheckIfAccountIsSynchronizingAsync();
-
             // Notify change for archive-unarchive app bar button.
             OnPropertyChanged(nameof(IsArchiveSpecialFolder));
 
@@ -865,6 +862,9 @@ namespace Wino.Mail.ViewModels
                 await Task.Delay(100);
             }
 
+            // Check whether the account synchronizer that this folder belongs to is already in synchronization.
+            await CheckIfAccountIsSynchronizingAsync();
+
             // Let awaiters know about the completion of mail init.
             message.FolderInitLoadAwaitTask?.TrySetResult(true);
 
diff --git a/Wino.Mail/App.xaml.cs b/Wino.Mail/App.xaml.cs
index c4e2d1ad..42d658f9 100644
--- a/Wino.Mail/App.xaml.cs
+++ b/Wino.Mail/App.xaml.cs
@@ -67,7 +67,6 @@ namespace Wino
         private List<IInitializeAsync> initializeServices => new List<IInitializeAsync>()
         {
             _databaseService,
-            _appServiceConnectionManager,
             _translationService,
             _themeService,
         };
@@ -77,8 +76,6 @@ namespace Wino
             InitializeComponent();
 
             UnhandledException += OnAppUnhandledException;
-            EnteredBackground += OnEnteredBackground;
-            LeavingBackground += OnLeavingBackground;
 
             Resuming += OnResuming;
             Suspending += OnSuspending;
@@ -126,8 +123,6 @@ namespace Wino
         }
 
         private void LogActivation(string log) => Log.Information($"{WinoLaunchLogPrefix}{log}");
-        private void OnLeavingBackground(object sender, LeavingBackgroundEventArgs e) => LogActivation($"Wino went foreground.");
-        private void OnEnteredBackground(object sender, EnteredBackgroundEventArgs e) => LogActivation($"Wino went background.");
         private IServiceProvider ConfigureServices()
         {
             var services = new ServiceCollection();
@@ -417,13 +412,11 @@ namespace Wino
             yield return Services.GetService<FileActivationHandler>();
         }
 
-        public async void OnConnectionBackgroundTaskCanceled(IBackgroundTaskInstance sender, BackgroundTaskCancellationReason reason)
+        public void OnConnectionBackgroundTaskCanceled(IBackgroundTaskInstance sender, BackgroundTaskCancellationReason reason)
         {
             sender.Canceled -= OnConnectionBackgroundTaskCanceled;
 
-            Log.Information($"Server connection background task '{sender.Task.Name}' was canceled. Reason: {reason}");
-
-            await _appServiceConnectionManager.DisconnectAsync();
+            Log.Information($"Server connection background task was canceled. Reason: {reason}");
 
             connectionBackgroundTaskDeferral?.Complete();
             connectionBackgroundTaskDeferral = null;
diff --git a/Wino.Server/ServerContext.cs b/Wino.Server/ServerContext.cs
index 9a60c63d..cf2ce174 100644
--- a/Wino.Server/ServerContext.cs
+++ b/Wino.Server/ServerContext.cs
@@ -173,7 +173,7 @@ namespace Wino.Server
 
             if (status != AppServiceConnectionStatus.Success)
             {
-                // TODO: Handle connection error
+                Log.Error("Opening server connection failed. Status: {status}", status);
 
                 DisposeConnection();
             }
@@ -224,8 +224,6 @@ namespace Wino.Server
 
         private void OnConnectionClosed(AppServiceConnection sender, AppServiceClosedEventArgs args)
         {
-            // TODO: Handle connection closed.
-
             // UWP app might've been terminated or suspended.
             // At this point, we must keep active synchronizations going, but connection is lost.
             // As long as this process is alive, database will be kept updated, but no messages will be sent.