diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptHistory.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptHistory.java
index 74d1269..1bf8c3a 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptHistory.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptHistory.java
@@ -16,9 +16,6 @@
 
 @Slf4j
 public class ChatGptHistory extends ChatGptComment {
-    private static final String ROLE_USER = "user";
-    private static final String ROLE_ASSISTANT = "assistant";
-
     private final Set<String> messagesExcludedFromHistory;
     private final HashMap<String, GerritComment> commentMap;
     private final HashMap<String, GerritComment> patchSetCommentMap;
@@ -89,7 +86,7 @@
     }
 
     private String getRoleFromComment(GerritComment currentComment) {
-        return isFromAssistant(currentComment) ? ROLE_ASSISTANT : ROLE_USER;
+        return isFromAssistant(currentComment) ? Settings.CHAT_GPT_ROLE_ASSISTANT : Settings.CHAT_GPT_ROLE_USER;
     }
 
     private List<ChatGptRequestMessage> retrieveMessageHistory(GerritComment currentComment) {
diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptBase.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptBase.java
index 95b931b..3c1e376 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptBase.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptBase.java
@@ -63,9 +63,9 @@
         return messageItem;
     }
 
-    protected void setHistories(ChatGptMessageItem messageItem, List<ChatGptRequestMessage> messageHistories) {
-        if (!messageHistories.isEmpty()) {
-            messageItem.setHistory(messageHistories);
+    protected void setHistory(ChatGptMessageItem messageItem, List<ChatGptRequestMessage> messageHistory) {
+        if (!messageHistory.isEmpty()) {
+            messageItem.setHistory(messageHistory);
         }
     }
 }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptRequests.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptRequests.java
index 2a3b214..4ccd5f1 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptRequests.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptRequests.java
@@ -10,10 +10,12 @@
 
 import java.util.List;
 
+import static com.googlesource.gerrit.plugins.chatgpt.settings.Settings.CHAT_GPT_ROLE_USER;
+
 @Slf4j
 public class ChatGptUserPromptRequests extends ChatGptUserPromptBase {
     protected ChatGptMessageItem messageItem;
-    protected List<ChatGptRequestMessage> messageHistories;
+    protected List<ChatGptRequestMessage> messageHistory;
 
     public ChatGptUserPromptRequests(
             Configuration config,
@@ -33,10 +35,20 @@
 
     protected ChatGptMessageItem getMessageItem(int i) {
         messageItem = super.getMessageItem(i);
-        messageHistories = gptMessageHistory.retrieveHistory(commentProperties.get(i));
-        ChatGptRequestMessage request = messageHistories.remove(messageHistories.size() -1);
+        messageHistory = gptMessageHistory.retrieveHistory(commentProperties.get(i));
+        ChatGptRequestMessage request = extractLastUserMessageFromHistory();
         messageItem.setRequest(request.getContent());
 
         return messageItem;
     }
+
+    private ChatGptRequestMessage extractLastUserMessageFromHistory() {
+        for (int i = messageHistory.size() - 1; i >= 0; i--) {
+            if (CHAT_GPT_ROLE_USER.equals(messageHistory.get(i).getRole())) {
+                return messageHistory.remove(i);
+            }
+        }
+        throw new RuntimeException("Error extracting request from message history: no user message found in " +
+                messageHistory);
+    }
 }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptReview.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptReview.java
index f307e58..acc51c0 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptReview.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/common/client/prompt/ChatGptUserPromptReview.java
@@ -33,9 +33,9 @@
 
     protected ChatGptMessageItem getMessageItem(int i) {
         ChatGptMessageItem messageItem = super.getMessageItem(i);
-        List<ChatGptRequestMessage> messageHistories = gptMessageHistory.retrieveHistory(commentProperties.get(i),
+        List<ChatGptRequestMessage> messageHistory = gptMessageHistory.retrieveHistory(commentProperties.get(i),
                 true);
-        setHistories(messageItem, messageHistories);
+        setHistory(messageItem, messageHistory);
 
         return messageItem;
     }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/stateless/client/prompt/ChatGptUserPromptRequestsStateless.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/stateless/client/prompt/ChatGptUserPromptRequestsStateless.java
index e792f11..a071116 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/stateless/client/prompt/ChatGptUserPromptRequestsStateless.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/mode/stateless/client/prompt/ChatGptUserPromptRequestsStateless.java
@@ -22,7 +22,7 @@
 
     protected ChatGptMessageItem getMessageItem(int i) {
         super.getMessageItem(i);
-        setHistories(messageItem, messageHistories);
+        setHistory(messageItem, messageHistory);
 
         return messageItem;
     }
diff --git a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/settings/Settings.java b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/settings/Settings.java
index 6a25733..091355c 100644
--- a/src/main/java/com/googlesource/gerrit/plugins/chatgpt/settings/Settings.java
+++ b/src/main/java/com/googlesource/gerrit/plugins/chatgpt/settings/Settings.java
@@ -16,6 +16,9 @@
     );
     public static final String GERRIT_COMMIT_MESSAGE_PREFIX = "Subject: ";
 
+    public static final String CHAT_GPT_ROLE_USER = "user";
+    public static final String CHAT_GPT_ROLE_ASSISTANT = "assistant";
+
     public enum MODES {
         stateless,
         stateful
diff --git a/src/test/java/com/googlesource/gerrit/plugins/chatgpt/ChatGptReviewStatelessTest.java b/src/test/java/com/googlesource/gerrit/plugins/chatgpt/ChatGptReviewStatelessTest.java
index a8b8ec2..b28bb7e 100644
--- a/src/test/java/com/googlesource/gerrit/plugins/chatgpt/ChatGptReviewStatelessTest.java
+++ b/src/test/java/com/googlesource/gerrit/plugins/chatgpt/ChatGptReviewStatelessTest.java
@@ -187,7 +187,7 @@
                 ChatGptPromptStateless.DEFAULT_GPT_REQUEST_PROMPT_DIFF,
                 diffContent,
                 ChatGptPromptStateless.DEFAULT_GPT_REQUEST_PROMPT_REQUESTS,
-                promptTagComments,
+                readTestFile("__files/stateless/chatGptExpectedRequestMessage.json"),
                 ChatGptPromptStateless.getCommentRequestUserPrompt(commentPropertiesSize)
         ));
         testRequestSent();
diff --git a/src/test/resources/__files/stateful/chatGptPromptTagRequests.json b/src/test/resources/__files/stateful/chatGptPromptTagRequests.json
index 4ab9486..106dfd4 100644
--- a/src/test/resources/__files/stateful/chatGptPromptTagRequests.json
+++ b/src/test/resources/__files/stateful/chatGptPromptTagRequests.json
@@ -1 +1 @@
-[{"request":"How about something like \"Corrected Indentation in Module-Class Retrieval Line\"?","id":0},{"request":"message","id":1},{"request":"message 2","id":2}]
\ No newline at end of file
+[{"request":"can you suggest an alternative commit message?","id":0},{"request":"message","id":1},{"request":"message 2","id":2}]
\ No newline at end of file
diff --git a/src/test/resources/__files/stateless/chatGptExpectedRequestMessage.json b/src/test/resources/__files/stateless/chatGptExpectedRequestMessage.json
new file mode 100644
index 0000000..f6e01d6
--- /dev/null
+++ b/src/test/resources/__files/stateless/chatGptExpectedRequestMessage.json
@@ -0,0 +1 @@
+[{"request":"can you suggest an alternative commit message?","history":[{"role":"user","content":"comment"},{"role":"user","content":"comment 2"},{"role":"assistant","content":"The commit message \u0027Minor Fixes\u0027 is too vague and does not provide enough context about the changes made. A more descriptive message that outlines the specific fixes or improvements would be beneficial."},{"role":"assistant","content":"How about something like \"Corrected Indentation in Module-Class Retrieval Line\"?"}],"id":0},{"request":"message","id":1,"filename":"test_file.py","lineNumber":5,"codeSnippet":"TypeClassOrPath"},{"request":"message 2","history":[{"role":"assistant","content":"message from gpt"}],"id":2,"filename":"test_file.py","lineNumber":5,"codeSnippet":"TypeClassOrPath"}]
\ No newline at end of file