diff --git a/src/interface/web/app/chat/page.tsx b/src/interface/web/app/chat/page.tsx
index ecd10a4f..0e913dc7 100644
--- a/src/interface/web/app/chat/page.tsx
+++ b/src/interface/web/app/chat/page.tsx
@@ -50,6 +50,7 @@ interface ChatBodyDataProps {
     setIsChatSideBarOpen: (open: boolean) => void;
     isActive?: boolean;
     isParentProcessing?: boolean;
+    onRetryMessage?: (query: string, turnId?: string) => void;
 }
 
 function ChatBodyData(props: ChatBodyDataProps) {
@@ -157,6 +158,7 @@ function ChatBodyData(props: ChatBodyDataProps) {
                         setIncomingMessages={props.setStreamedMessages}
                         customClassName={chatHistoryCustomClassName}
                         setIsChatSideBarOpen={props.setIsChatSideBarOpen}
+                        onRetryMessage={props.onRetryMessage}
                     />
                 </div>
                 <div
@@ -422,6 +424,36 @@ export default function Chat() {
         setConversationID(newConversationId);
     };
 
+    const handleRetryMessage = (query: string, turnId?: string) => {
+        if (!query) {
+            console.warn("No query provided for retry");
+            return;
+        }
+
+        // If we have a turnId, delete the old turn first
+        if (turnId) {
+            // Delete from streaming messages if present
+            setMessages((prevMessages) => prevMessages.filter((msg) => msg.turnId !== turnId));
+
+            // Also call the delete API to remove from conversation history
+            fetch("/api/chat/conversation/message", {
+                method: "DELETE",
+                headers: {
+                    "Content-Type": "application/json",
+                },
+                body: JSON.stringify({
+                    conversation_id: conversationId,
+                    turn_id: turnId,
+                }),
+            }).catch((error) => {
+                console.error("Failed to delete message for retry:", error);
+            });
+        }
+
+        // Re-send the original query
+        setQueryToProcess(query);
+    };
+
     if (isLoading) return <Loading />;
 
     return (
@@ -491,6 +523,7 @@ export default function Chat() {
                                     setIsChatSideBarOpen={setIsChatSideBarOpen}
                                     isActive={authenticatedData?.is_active}
                                     isParentProcessing={processQuerySignal}
+                                    onRetryMessage={handleRetryMessage}
                                 />
                             </Suspense>
                         </div>
diff --git a/src/interface/web/app/components/chatHistory/chatHistory.tsx b/src/interface/web/app/components/chatHistory/chatHistory.tsx
index 94f12650..bd97bb31 100644
--- a/src/interface/web/app/components/chatHistory/chatHistory.tsx
+++ b/src/interface/web/app/components/chatHistory/chatHistory.tsx
@@ -41,6 +41,7 @@ interface ChatHistoryProps {
     customClassName?: string;
     setIsChatSideBarOpen?: (isOpen: boolean) => void;
     setIsOwner?: (isOwner: boolean) => void;
+    onRetryMessage?: (query: string, turnId?: string) => void;
 }
 
 interface TrainOfThoughtFrame {
@@ -508,6 +509,18 @@ export default function ChatHistory(props: ChatHistoryProps) {
         }
     };
 
+    const handleRetryMessage = (query: string, turnId?: string) => {
+        if (!query) return;
+
+        // Delete the message from local state first
+        if (turnId) {
+            handleDeleteMessage(turnId);
+        }
+
+        // Then trigger the retry
+        props.onRetryMessage?.(query, turnId);
+    };
+
     if (!props.conversationId && !props.publicConversationSlug) {
         return null;
     }
@@ -561,6 +574,7 @@ export default function ChatHistory(props: ChatHistoryProps) {
                                     borderLeftColor={`${data?.agent?.color}-500`}
                                     isLastMessage={index === data.chat.length - 1}
                                     onDeleteMessage={handleDeleteMessage}
+                                    onRetryMessage={handleRetryMessage}
                                     conversationId={props.conversationId}
                                 />
                             </React.Fragment>
@@ -589,6 +603,7 @@ export default function ChatHistory(props: ChatHistoryProps) {
                                         customClassName="fullHistory"
                                         borderLeftColor={`${data?.agent?.color}-500`}
                                         onDeleteMessage={handleDeleteMessage}
+                                        onRetryMessage={handleRetryMessage}
                                         conversationId={props.conversationId}
                                         turnId={messageTurnId}
                                     />
@@ -629,6 +644,7 @@ export default function ChatHistory(props: ChatHistoryProps) {
                                         conversationId={props.conversationId}
                                         turnId={messageTurnId}
                                         onDeleteMessage={handleDeleteMessage}
+                                        onRetryMessage={handleRetryMessage}
                                         customClassName="fullHistory"
                                         borderLeftColor={`${data?.agent?.color}-500`}
                                         isLastMessage={index === props.incomingMessages!.length - 1}
@@ -653,6 +669,7 @@ export default function ChatHistory(props: ChatHistoryProps) {
                             }}
                             conversationId={props.conversationId}
                             onDeleteMessage={handleDeleteMessage}
+                            onRetryMessage={handleRetryMessage}
                             customClassName="fullHistory"
                             borderLeftColor={`${data?.agent?.color}-500`}
                             isLastMessage={true}
diff --git a/src/interface/web/app/components/chatMessage/chatMessage.module.css b/src/interface/web/app/components/chatMessage/chatMessage.module.css
index 5309c175..a31f0bdc 100644
--- a/src/interface/web/app/components/chatMessage/chatMessage.module.css
+++ b/src/interface/web/app/components/chatMessage/chatMessage.module.css
@@ -158,7 +158,8 @@ button.codeCopyButton:hover {
 
 div.feedbackButtons img,
 button.codeCopyButton img,
-button.copyButton img {
+button.copyButton img,
+button.retryButton img {
     width: 24px;
 }
 
diff --git a/src/interface/web/app/components/chatMessage/chatMessage.tsx b/src/interface/web/app/components/chatMessage/chatMessage.tsx
index f34cf11d..e25dc814 100644
--- a/src/interface/web/app/components/chatMessage/chatMessage.tsx
+++ b/src/interface/web/app/components/chatMessage/chatMessage.tsx
@@ -32,6 +32,7 @@ import {
     Trash,
     Toolbox,
     Browser,
+    ArrowClockwise,
 } from "@phosphor-icons/react";
 
 import DOMPurify from "dompurify";
@@ -273,6 +274,7 @@ interface ChatMessageProps {
     isLastMessage?: boolean;
     agent?: AgentData;
     onDeleteMessage: (turnId?: string) => void;
+    onRetryMessage?: (query: string, turnId?: string) => void;
     conversationId: string;
     turnId?: string;
     generatedImage?: string;
@@ -814,6 +816,38 @@ const ChatMessage = forwardRef<HTMLDivElement, ChatMessageProps>((props, ref) =>
                                     />
                                 </button>
                             )}
+                            {props.chatMessage.by === "khoj" && props.onRetryMessage && props.isLastMessage && (
+                                <button
+                                    title="Retry"
+                                    className={`${styles.retryButton}`}
+                                    onClick={() => {
+                                        const turnId = props.chatMessage.turnId || props.turnId;
+                                        const query = props.chatMessage.rawQuery || props.chatMessage.intent?.query;
+                                        console.log("Retry button clicked for turnId:", turnId);
+                                        console.log("ChatMessage data:", {
+                                            rawQuery: props.chatMessage.rawQuery,
+                                            intent: props.chatMessage.intent,
+                                            message: props.chatMessage.message
+                                        });
+                                        console.log("Extracted query:", query);
+                                        if (query) {
+                                            props.onRetryMessage?.(query, turnId);
+                                        } else {
+                                            console.error("No original query found for retry");
+                                            // Fallback: try to get from a previous user message or show an input dialog
+                                            const fallbackQuery = prompt("Enter the original query to retry:");
+                                            if (fallbackQuery) {
+                                                props.onRetryMessage?.(fallbackQuery, turnId);
+                                            }
+                                        }
+                                    }}
+                                >
+                                    <ArrowClockwise
+                                        alt="Retry Message"
+                                        className="hsl(var(--muted-foreground)) hover:text-blue-500"
+                                    />
+                                </button>
+                            )}
                             <button
                                 title="Copy"
                                 className={`${styles.copyButton}`}