diff --git a/AI.NET/Resources/Strings/Strings.Designer.cs b/AI.NET/Resources/Strings/Strings.Designer.cs
index bc94c22..b84485f 100644
--- a/AI.NET/Resources/Strings/Strings.Designer.cs
+++ b/AI.NET/Resources/Strings/Strings.Designer.cs
@@ -70,11 +70,11 @@ public static string About {
         }
         
         /// <summary>
-        ///   查找类似 Delete Current Chat (Ctrl+D) 的本地化字符串。
+        ///   查找类似 Retry Last AI Response (Ctrl+R) 的本地化字符串。
         /// </summary>
-        public static string DeleteChat {
+        public static string RetryGeneration {
             get {
-                return ResourceManager.GetString("DeleteChat", resourceCulture);
+                return ResourceManager.GetString("RetryGeneration", resourceCulture);
             }
         }
         
diff --git a/AI.NET/Resources/Strings/Strings.resx b/AI.NET/Resources/Strings/Strings.resx
index 307f96a..e11d51b 100644
--- a/AI.NET/Resources/Strings/Strings.resx
+++ b/AI.NET/Resources/Strings/Strings.resx
@@ -120,8 +120,8 @@
   <data name="About" xml:space="preserve">
     <value>About</value>
   </data>
-  <data name="DeleteChat" xml:space="preserve">
-    <value>Delete Current Chat (Ctrl+D)</value>
+  <data name="RetryGeneration" xml:space="preserve">
+    <value>Retry Last AI Response (Ctrl+R)</value>
   </data>
   <data name="Mem0ServerUrl" xml:space="preserve">
     <value>Mem0 Server URL</value>
diff --git a/AI.NET/Resources/Strings/Strings.zh-CHS.resx b/AI.NET/Resources/Strings/Strings.zh-CHS.resx
index 297d6e3..088c0e0 100644
--- a/AI.NET/Resources/Strings/Strings.zh-CHS.resx
+++ b/AI.NET/Resources/Strings/Strings.zh-CHS.resx
@@ -120,8 +120,8 @@
   <data name="About" xml:space="preserve">
     <value>关于</value>
   </data>
-  <data name="DeleteChat" xml:space="preserve">
-    <value>删除当前聊天 (Ctrl+D)</value>
+  <data name="RetryGeneration" xml:space="preserve">
+    <value>重新生成 AI 回复 (Ctrl+R)</value>
   </data>
   <data name="Mem0ServerUrl" xml:space="preserve">
     <value>Mem0 服务器地址</value>
diff --git a/AI.NET/Resources/Strings/Strings.zh-CN.resx b/AI.NET/Resources/Strings/Strings.zh-CN.resx
index a2e4900..c90319a 100644
--- a/AI.NET/Resources/Strings/Strings.zh-CN.resx
+++ b/AI.NET/Resources/Strings/Strings.zh-CN.resx
@@ -123,8 +123,8 @@
   <data name="About" xml:space="preserve">
     <value>关于</value>
   </data>
-  <data name="DeleteChat" xml:space="preserve">
-    <value>删除当前聊天 (Ctrl+D)</value>
+  <data name="RetryGeneration" xml:space="preserve">
+    <value>重新生成 AI 回复 (Ctrl+R)</value>
   </data>
   <data name="Mem0ServerUrl" xml:space="preserve">
     <value>Mem0 服务器地址</value>
diff --git a/AI.NET/Service/AI.cs b/AI.NET/Service/AI.cs
index 6a79882..644b31b 100644
--- a/AI.NET/Service/AI.cs
+++ b/AI.NET/Service/AI.cs
@@ -40,11 +40,53 @@ public static async Task RequestAIAsync(string message, MarkdownScrollViewer out
             TopicsHelper.SaveTopicsAsync(Topics);
         }
         /// <summary>
-        /// Delete a chat session
+        /// Retry generating the last AI response
         /// </summary>
-        public static void DeleteMessages()
+        /// <param name="outputBox">The UI element to update</param>
+        public static async Task RetryLastResponseAsync(MarkdownScrollViewer outputBox)
         {
-            Topics.RemoveAt(Topics.CurrentTopicIndex);
+            var messages = Topics.CurrentTopic.MessageList;
+            
+            // Find the last user message and remove any subsequent AI/system messages
+            int lastUserIndex = -1;
+            for (int i = messages.Count - 1; i >= 0; i--)
+            {
+                if (messages[i].Role == ChatMessageRole.User)
+                {
+                    lastUserIndex = i;
+                    break;
+                }
+            }
+            
+            if (lastUserIndex == -1)
+            {
+                return; // No user message found to retry
+            }
+            
+            // Remove all messages after the last user message
+            while (messages.Count > lastUserIndex + 1)
+            {
+                messages.RemoveAt(messages.Count - 1);
+            }
+            
+            string lastUserMessage = messages[lastUserIndex].Content;
+            
+            // Update the output box to show we're retrying
+            string currentMarkdown = await Topics.CurrentTopic.GetMarkdownAsync();
+            outputBox.Markdown = currentMarkdown + "AI:";
+            
+            // Handle memory if enabled
+            if (Mem0.IsEnabled)
+                await HandleMemoryAsync(lastUserMessage);
+            
+            // Generate new AI response
+            Topics.CurrentTopic.Add(new Chat()
+            {
+                Content = await OpenAI.GenerateReplyAsync(outputBox),
+                Role = ChatMessageRole.Assistant
+            });
+            
+            // Save topics to file
             TopicsHelper.SaveTopicsAsync(Topics);
         }
         public static void NewChat(Data.SystemPrompt prompt)
diff --git a/AI.NET/Windows/MainWindow.xaml b/AI.NET/Windows/MainWindow.xaml
index 75823f5..c1460dc 100644
--- a/AI.NET/Windows/MainWindow.xaml
+++ b/AI.NET/Windows/MainWindow.xaml
@@ -64,8 +64,8 @@
                 <Button x:Name="newButton" Click="NewChatButton_Click" Margin="10,0,0,0" ToolTip="{x:Static strings:Strings.NewChat}">
                     <ic:FluentIcon Icon="CommentAdd" IconVariant="Regular"/>
                 </Button>
-                <Button x:Name="deleteChatButton" Click="DeleteChatButton_Click" Margin="10,0,0,0" ToolTip="{x:Static strings:Strings.DeleteChat}">
-                    <ic:FluentIcon Icon="Delete" IconVariant="Filled" Foreground="Red"/>
+                <Button x:Name="retryButton" Click="RetryButton_Click" Margin="10,0,0,0" ToolTip="{x:Static strings:Strings.RetryGeneration}">
+                    <ic:FluentIcon Icon="ArrowClockwise" IconVariant="Filled" Foreground="Orange"/>
                 </Button>
             </StackPanel>
         </Grid>
diff --git a/AI.NET/Windows/MainWindow.xaml.cs b/AI.NET/Windows/MainWindow.xaml.cs
index 5d4ab5b..dfade1a 100644
--- a/AI.NET/Windows/MainWindow.xaml.cs
+++ b/AI.NET/Windows/MainWindow.xaml.cs
@@ -87,7 +87,7 @@ private void SetBusyState(bool isBusy)
             sendButton.IsChecked = isBusy;
             sendButton.IsEnabled = !isBusy;
             newButton.IsEnabled = !isBusy;
-            deleteChatButton.IsEnabled = !isBusy;
+            retryButton.IsEnabled = !isBusy;
         }
         private void NewChatButton_Click(object sender, RoutedEventArgs e)
         {
@@ -98,14 +98,25 @@ private void NewChatButton_Click(object sender, RoutedEventArgs e)
             topicBox.SelectedIndex = Service.AI.Topics.TopicList.Count - 1;
         }
 
-        private void DeleteChatButton_Click(object sender, RoutedEventArgs e)
+        private async void RetryButton_Click(object sender, RoutedEventArgs e)
         {
             if (topicBox.SelectedIndex >= 0 && topicBox.Items.Count > 0)
             {
-                outputBox.Markdown = string.Empty;
-                int index = topicBox.SelectedIndex;
-                Service.AI.DeleteMessages();
-                topicBox.SelectedIndex = index - 1;
+                SetBusyState(true);
+                try
+                {
+                    await Service.AI.RetryLastResponseAsync(outputBox);
+                }
+                catch (Exception ex)
+                {
+                    Growl.Error(new() { StaysOpen = true, Message = ex.Message });
+                    Log.Error("Error when retrying AI response", ex);
+                }
+                finally
+                {
+                    outputBox.Markdown += markdownNewLine;
+                    SetBusyState(false);
+                }
             }
         }
 
@@ -165,8 +176,8 @@ private void Window_KeyDown(object sender, KeyEventArgs e)
                     NewChatButton_Click(sender, e);
                 else if (e.Key == Key.Enter)
                     SendButton_Click(sender, e);
-                else if (e.Key == Key.D)
-                    DeleteChatButton_Click(sender, e);
+                else if (e.Key == Key.R)
+                    RetryButton_Click(sender, e);
             }
         }