diff --git a/src/main/java/ee/carlrobert/codegpt/toolwindow/ToolWindowService.java b/src/main/java/ee/carlrobert/codegpt/toolwindow/ToolWindowService.java
index c6d5791c..e6c0c9e1 100644
--- a/src/main/java/ee/carlrobert/codegpt/toolwindow/ToolWindowService.java
+++ b/src/main/java/ee/carlrobert/codegpt/toolwindow/ToolWindowService.java
@@ -33,11 +33,19 @@ public class ToolWindowService implements LafManagerListener {
     return chatToolWindow;
   }
 
-  public void startRequest(String prompt, SyntaxTextArea textArea, Project project) {
+  public void startRequest(String prompt, SyntaxTextArea textArea, Project project, boolean isRetry) {
     var conversationsState = ConversationsState.getInstance();
     var currentConversation = ConversationsState.getCurrentConversation();
     var conversation = currentConversation == null ? conversationsState.startConversation() : currentConversation;
-    var conversationMessage = new Message(prompt);
+
+    Message conversationMessage;
+    if (isRetry) {
+      var messages = conversation.getMessages();
+      conversationMessage = messages.get(messages.size() - 1);
+      conversationMessage.setResponse("");
+    } else {
+      conversationMessage = new Message(prompt);
+    }
 
     new SwingWorker<Void, String>() {
       protected Void doInBackground() {
diff --git a/src/main/java/ee/carlrobert/codegpt/toolwindow/chat/ChatGptToolWindow.java b/src/main/java/ee/carlrobert/codegpt/toolwindow/chat/ChatGptToolWindow.java
index cb0cb373..d664ecb1 100644
--- a/src/main/java/ee/carlrobert/codegpt/toolwindow/chat/ChatGptToolWindow.java
+++ b/src/main/java/ee/carlrobert/codegpt/toolwindow/chat/ChatGptToolWindow.java
@@ -129,16 +129,28 @@ public class ChatGptToolWindow {
   }
 
   public void sendMessage(String prompt, Project project) {
-    addIconLabel(Icons.DefaultImageIcon, "ChatGPT");
+    sendMessage(prompt, project, false);
+  }
+
+  public void sendMessage(String prompt, Project project, boolean isRetry) {
+    if (!isRetry) {
+      addIconLabel(Icons.DefaultImageIcon, "ChatGPT");
+    }
 
     var settings = SettingsState.getInstance();
     if (settings.apiKey.isEmpty()) {
       notifyMissingCredential(project, "API key not provided.");
     } else {
-      var textArea = new SyntaxTextArea(true, true, SyntaxConstants.SYNTAX_STYLE_MARKDOWN);
-      addTextArea(textArea);
+      SyntaxTextArea textArea;
+      if (isRetry) {
+        textArea = textAreas.get(textAreas.size() - 1);
+        textArea.clear();
+      } else {
+        textArea = new SyntaxTextArea(true, true, SyntaxConstants.SYNTAX_STYLE_MARKDOWN);
+        addTextArea(textArea);
+      }
       project.getService(ToolWindowService.class)
-          .startRequest(prompt, textArea, project);
+          .startRequest(prompt, textArea, project, isRetry);
     }
   }
 
@@ -177,11 +189,11 @@ public class ChatGptToolWindow {
 
   public void stopGenerating(String prompt, SyntaxTextArea textArea, Project project) {
     generateButton.setMode(GenerateButton.Mode.REFRESH, () -> {
-      sendMessage(prompt, project);
+      sendMessage(prompt, project, true);
       scrollToBottom();
     });
     textArea.displayCopyButton();
-    textArea.hideCaret();
+    textArea.getCaret().setVisible(false);
     scrollToBottom();
   }
 
diff --git a/src/main/java/ee/carlrobert/codegpt/toolwindow/components/SyntaxTextArea.java b/src/main/java/ee/carlrobert/codegpt/toolwindow/components/SyntaxTextArea.java
index 460682d4..b80bf221 100644
--- a/src/main/java/ee/carlrobert/codegpt/toolwindow/components/SyntaxTextArea.java
+++ b/src/main/java/ee/carlrobert/codegpt/toolwindow/components/SyntaxTextArea.java
@@ -28,10 +28,6 @@ public class SyntaxTextArea extends RSyntaxTextArea {
     cb.install(this);
   }
 
-  public void hideCaret() {
-    getCaret().setVisible(false);
-  }
-
   public void changeStyleViaThemeXml() {
     var baseThemePath = "/org/fife/ui/rsyntaxtextarea/themes/";
     try {
@@ -44,6 +40,14 @@ public class SyntaxTextArea extends RSyntaxTextArea {
     }
   }
 
+  public void clear() {
+    removeAll();
+    setText("");
+    getCaret().setVisible(true);
+    revalidate();
+    repaint();
+  }
+
   private void setStyles(boolean isReadOnly, boolean withBlockCaret, String syntax) {
     setMargin(JBUI.insets(5));
     setAntiAliasingEnabled(true);
diff --git a/src/main/resources/META-INF/plugin.xml b/src/main/resources/META-INF/plugin.xml
index eb917a48..ff9945e0 100644
--- a/src/main/resources/META-INF/plugin.xml
+++ b/src/main/resources/META-INF/plugin.xml
@@ -86,7 +86,7 @@
     </projectListeners>
 
     <extensions defaultExtensionNs="com.intellij">
-        <postStartupActivity implementation="ee.carlrobert.codegpt.PluginStartupActivity" />
+        <postStartupActivity implementation="ee.carlrobert.codegpt.PluginStartupActivity"/>
         <applicationConfigurable id="settings.codegpt" parentId="tools" displayName="CodeGPT"
             instance="ee.carlrobert.codegpt.settings.SettingsConfigurable"/>
         <applicationConfigurable id="settings.codegpt.configuration" parentId="settings.codegpt" displayName="Configuration"