diff --git a/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection.Contracts/IChangeServerModerator.cs b/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection.Contracts/IChangeServerModerator.cs
index 04977643d..8642a6712 100644
--- a/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection.Contracts/IChangeServerModerator.cs
+++ b/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection.Contracts/IChangeServerModerator.cs
@@ -28,4 +28,6 @@ public interface IChangeServerModerator
     TimeSpan GetDelayUntilNextAttempt();
 
     TimeSpan GetRemainingDelayUntilNextAttempt();
+
+    bool HasTroubleConnecting();
 }
\ No newline at end of file
diff --git a/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection/ChangeServerModerator.cs b/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection/ChangeServerModerator.cs
index ddc88a17a..dd4db03ef 100644
--- a/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection/ChangeServerModerator.cs
+++ b/src/Client/Logic/Connection/ProtonVPN.Client.Logic.Connection/ChangeServerModerator.cs
@@ -39,12 +39,16 @@ public class ChangeServerModerator :
     IEventMessageReceiver<SettingChangedMessage>,
     IEventMessageReceiver<ConnectionStatusChangedMessage>
 {
+    private const int TroubleConnectingDelaySeconds = 6;
+
     private readonly ISettings _settings;
     private readonly IConnectionManager _connectionManager;
     private readonly IEventMessageSender _eventMessageSender;
 
     private ChangeServerSettings _changeServerSettings;
     private ChangeServerAttempts _changeServerAttempts;
+    private DateTimeOffset? _connectionStartTime;
+    private bool _isConnecting;
 
     protected override TimeSpan PollingInterval { get; } = TimeSpan.FromSeconds(1);
 
@@ -92,6 +96,17 @@ public TimeSpan GetRemainingDelayUntilNextAttempt()
             : TimeSpan.FromSeconds(Math.Ceiling(remainingTime.TotalSeconds));
     }
 
+    public bool HasTroubleConnecting()
+    {
+        if (!_isConnecting || !_connectionStartTime.HasValue)
+        {
+            return false;
+        }
+
+        TimeSpan elapsedTime = DateTimeOffset.UtcNow - _connectionStartTime.Value;
+        return elapsedTime.TotalSeconds >= TroubleConnectingDelaySeconds;
+    }
+
     public void Receive(LoggedInMessage message)
     {
         InvalidateChangeServerAttempts();
@@ -116,6 +131,20 @@ public void Receive(SettingChangedMessage message)
 
     public void Receive(ConnectionStatusChangedMessage message)
     {
+        // Track connection state for HasTroubleConnecting logic
+        switch (message.ConnectionStatus)
+        {
+            case ConnectionStatus.Connecting:
+                _isConnecting = true;
+                _connectionStartTime = DateTimeOffset.UtcNow;
+                break;
+            case ConnectionStatus.Connected:
+            case ConnectionStatus.Disconnected:
+                _isConnecting = false;
+                _connectionStartTime = null;
+                break;
+        }
+
         if (_connectionManager.IsConnected &&
             _connectionManager.CurrentConnectionIntent?.Location is FreeServerLocationIntent intent &&
            intent.Kind == ConnectionIntentKind.Random)
diff --git a/src/Client/ProtonVPN.Client/UI/Main/Home/Upsell/ChangeServerComponentViewModel.cs b/src/Client/ProtonVPN.Client/UI/Main/Home/Upsell/ChangeServerComponentViewModel.cs
index 924db1764..9e613ef90 100644
--- a/src/Client/ProtonVPN.Client/UI/Main/Home/Upsell/ChangeServerComponentViewModel.cs
+++ b/src/Client/ProtonVPN.Client/UI/Main/Home/Upsell/ChangeServerComponentViewModel.cs
@@ -47,6 +47,7 @@ public partial class ChangeServerComponentViewModel : ActivatableViewModelBase,
     public double DelayInSeconds => _changeServerModerator.GetDelayUntilNextAttempt().TotalSeconds;
     public double RemainingDelayInSeconds => _changeServerModerator.GetRemainingDelayUntilNextAttempt().TotalSeconds;
     public string? FormattedRemainingTime => Localizer.GetFormattedShortTime(_changeServerModerator.GetRemainingDelayUntilNextAttempt());
+    public bool HasTroubleConnecting => _changeServerModerator.HasTroubleConnecting();
 
     public ChangeServerComponentViewModel(
         IConnectionManager connectionManager,
@@ -99,7 +100,10 @@ private Task ChangeServerAsync()
 
     private bool CanChangeServer()
     {
-        return _connectionManager.IsConnected && _changeServerModerator.CanChangeServer();
+        bool isConnectedOrHasTroubleConnecting = _connectionManager.IsConnected || 
+                                                 (_connectionManager.IsConnecting && _changeServerModerator.HasTroubleConnecting());
+
+        return isConnectedOrHasTroubleConnecting && _changeServerModerator.CanChangeServer();
     }
 
     [RelayCommand]
@@ -115,6 +119,7 @@ private void InvalidateChangeServer()
         OnPropertyChanged(nameof(DelayInSeconds));
         OnPropertyChanged(nameof(RemainingDelayInSeconds));
         OnPropertyChanged(nameof(FormattedRemainingTime));
+        OnPropertyChanged(nameof(HasTroubleConnecting));
 
         ChangeServerCommand.NotifyCanExecuteChanged();
     }