diff --git a/BeWo/View/Controls/AI/AiChatButton.xaml b/BeWo/View/Controls/AI/AiChatButton.xaml
index 06fa3f743..ad8192e0b 100644
--- a/BeWo/View/Controls/AI/AiChatButton.xaml
+++ b/BeWo/View/Controls/AI/AiChatButton.xaml
@@ -19,7 +19,7 @@
             </ResourceDictionary.MergedDictionaries>
         </ResourceDictionary>
     </UserControl.Resources>
-    <Grid>
+    <Grid Visibility="{Binding IsVisible, Converter={StaticResource BoolVisibilityConverter}}">
         <StackPanel
             Margin="0"
             VerticalAlignment="Center"
diff --git a/BeWo/View/Controls/AI/AiChatButton.xaml.cs b/BeWo/View/Controls/AI/AiChatButton.xaml.cs
index 1c0e8bd30..011824bca 100644
--- a/BeWo/View/Controls/AI/AiChatButton.xaml.cs
+++ b/BeWo/View/Controls/AI/AiChatButton.xaml.cs
@@ -71,7 +71,7 @@ namespace BeWo.View.Controls.AI
 
 		private void ItemAccepted(object sender, AbstractBaseVM e)
 		{
-			throw new NotImplementedException();
+			ViewModel.ItemAccepted(e);
 		}
 
 		private void btnOpenAi5_MouseRightButtonUp(object sender, MouseButtonEventArgs e)
diff --git a/BeWo/ViewModel/Controls/AI/AiChatButtonViewModel.cs b/BeWo/ViewModel/Controls/AI/AiChatButtonViewModel.cs
index 06d84c645..8b160761f 100644
--- a/BeWo/ViewModel/Controls/AI/AiChatButtonViewModel.cs
+++ b/BeWo/ViewModel/Controls/AI/AiChatButtonViewModel.cs
@@ -9,6 +9,7 @@ using System;
 using System.Collections.Generic;
 using System.Linq;
 using System.Windows;
+using System.Windows.Input;
 
 namespace BeWo.ViewModel.Controls.AI
 {
@@ -23,6 +24,7 @@ namespace BeWo.ViewModel.Controls.AI
 
 	public class AiChatButtonViewModel : AbstractBaseVM
 	{
+		private bool isVisible;
 		private bool canExecute;
 		private AiChatButtonState buttonState;
 
@@ -34,11 +36,17 @@ namespace BeWo.ViewModel.Controls.AI
 
 		public bool IsEnabled => BeWoApp.AppSettings.ShowAI && BeWoApp.HasLoggedOnUserRight(GetUserRightType());
 
+		public bool IsVisible
+		{
+			get => isVisible;
+			set => SetProperty(ref isVisible, value, nameof(IsVisible));
+		}
 		public bool CanExecute
 		{
 			get => canExecute;
 			set => SetProperty(ref canExecute, value, nameof(CanExecute));
 		}
+
 		public AiChatButtonState ButtonState
 		{
 			get => buttonState;
@@ -47,6 +55,10 @@ namespace BeWo.ViewModel.Controls.AI
 					return;
 
 				FirePropertyChanged(nameof(IsContextSizeTooBig));
+				FirePropertyChanged(nameof(CanSendNewMessage));
+				FirePropertyChanged(nameof(CanOpenConversation));
+
+				CommandManager.InvalidateRequerySuggested();
 			}
 		}
 
@@ -59,6 +71,8 @@ namespace BeWo.ViewModel.Controls.AI
 		public DelegateCommand OpenFavoritePromptsPopupCommand { get; protected set; }
 
 		public bool IsContextSizeTooBig => ButtonState == AiChatButtonState.Warning;
+		public virtual bool CanSendNewMessage => ButtonState == AiChatButtonState.Normal;
+		public bool CanOpenConversation => ButtonState == AiChatButtonState.Normal || ButtonState == AiChatButtonState.Warning;
 
 		public AiChatButtonViewModel(AiActionType aiActionType)
 		{
@@ -67,11 +81,12 @@ namespace BeWo.ViewModel.Controls.AI
 			if (!IsEnabled)
 				return;
 
-			canExecute = true;
+			canExecute = false;
+			isVisible = false;
 
-			OpenConversationPopupCommand = new DelegateCommand(OpenConversationPopup);
-			OpenAllPromptsPopupCommand = new DelegateCommand(OpenAllPromptsPopup);
-			OpenFavoritePromptsPopupCommand = new DelegateCommand(OpenFavoritePromptsPopup);
+			OpenConversationPopupCommand = new DelegateCommand(OpenConversationPopup, () => CanOpenConversation);
+			OpenAllPromptsPopupCommand = new DelegateCommand(OpenAllPromptsPopup, () => CanSendNewMessage);
+			OpenFavoritePromptsPopupCommand = new DelegateCommand(OpenFavoritePromptsPopup, () => CanSendNewMessage);
 		}
 
 		public void CheckContextSize()
@@ -85,6 +100,15 @@ namespace BeWo.ViewModel.Controls.AI
 			var context = GetAiVisualContext();
 			if (context != null)
 			{
+				if(context.Primary is null)
+				{
+					IsVisible = false;
+					ButtonState = AiChatButtonState.Disabled;
+					return;
+				}
+
+				IsVisible = true;
+
 				var context2 = context.References.ToDictionary(kv => kv.Key, kv => kv.Value.ToList());
 
 				ServiceFacade.DoAiEnhancedServiceAsnyc(x => x.CheckContextSize(ActionType, context2, null),
@@ -99,13 +123,18 @@ namespace BeWo.ViewModel.Controls.AI
 			}
 		}
 
-		private protected void OpenConversationPopup()
+		private protected AiConversationChatViewModel GetConversationViewModel()
 		{
 			var context = GetAiVisualContext();
 
-			var chat_viewmodel = VMFactory.CreateAiConversationChatViewModel(ActionType, context.References, (long)context.Primary, true);
+			var chat_viewmodel = VMFactory.CreateAiConversationChatViewModel(ActionType, context.References, (long)context.Primary, CanSendNewMessage);
 
-			BeWoApp.MainControl.WindowService.Show(chat_viewmodel);
+			return chat_viewmodel;
+		}
+
+		private protected void OpenConversationPopup()
+		{
+			BeWoApp.MainControl.WindowService.Show(GetConversationViewModel());
 		}
 
 		private protected void OpenAllPromptsPopup()
@@ -135,6 +164,23 @@ namespace BeWo.ViewModel.Controls.AI
 
 			throw new InvalidOperationException($"UserRightType '{ActionType}' not implemented");
 		}
+
+		public void ItemAccepted(AbstractBaseVM e)
+		{
+			if(e is AiPromptbausteinPromptVM prompt)
+			{
+				var vm = GetConversationViewModel();
+				vm.SendAfterLoaded = true;
+				vm.MessageInput = prompt.Prompt;
+				BeWoApp.MainControl.WindowService.Show(vm);
+			}
+			else if(e is AiPromptbausteinRoutineVM routine)
+			{
+
+			}
+
+			throw new NotImplementedException();
+		}
 	}
 
 	public class AiMenuItemTemplate
diff --git a/BeWo/ViewModel/Controls/AI/AiChatButtonWithHistoryViewModel.cs b/BeWo/ViewModel/Controls/AI/AiChatButtonWithHistoryViewModel.cs
index 6f8dc2223..ae4ed44b7 100644
--- a/BeWo/ViewModel/Controls/AI/AiChatButtonWithHistoryViewModel.cs
+++ b/BeWo/ViewModel/Controls/AI/AiChatButtonWithHistoryViewModel.cs
@@ -51,13 +51,10 @@ namespace BeWo.ViewModel.Controls.AI
 			};
 			UndoAiActionCommand= new DelegateCommand(UndoAiAction);
 			RedoAiActionCommand= new DelegateCommand(RedoAiAction);
-
-			Func<bool> canExecute = () => !string.IsNullOrEmpty(CurrentValue);
-			OpenAllPromptsPopupCommand = new DelegateCommand(OpenAllPromptsPopup, canExecute);
-			OpenConversationPopupCommand = new DelegateCommand(OpenConversationPopup, canExecute);
-			OpenFavoritePromptsPopupCommand = new DelegateCommand(OpenFavoritePromptsPopup, canExecute);
 		}
 
+		public override bool CanSendNewMessage => base.CanSendNewMessage && !string.IsNullOrEmpty(CurrentValue);
+
 		public void ClearHistory()
 		{
 			History.Clear();