diff --git a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
index da134c4cf..10abe13b1 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
@@ -77,7 +77,10 @@ import {
 	type ThreadListResponse,
 	type ThreadRecord,
 } from "@/lib/chat/thread-persistence";
-import { extractUserTurnForNewChatApi } from "@/lib/chat/user-turn-api-parts";
+import {
+	extractUserTurnForNewChatApi,
+	type NewChatUserImagePayload,
+} from "@/lib/chat/user-turn-api-parts";
 import { NotFoundError } from "@/lib/error";
 import {
 	trackChatCreated,
@@ -1337,15 +1340,24 @@ export default function NewChatPage() {
 	 * Handle regeneration (edit or reload) by calling the regenerate endpoint
 	 * and streaming the response. This rewinds the LangGraph checkpointer state.
 	 *
-	 * @param newUserQuery - The new user query (for edit). Pass null/undefined for reload.
+	 * @param newUserQuery - `null` = reload with same turn from the server. A string = edit
+	 *   (including an empty string when the edited turn is images-only); pass `editExtras` for images/content.
 	 */
 	const handleRegenerate = useCallback(
-		async (newUserQuery?: string | null) => {
+		async (
+			newUserQuery: string | null,
+			editExtras?: {
+				userMessageContent: ThreadMessageLike["content"];
+				userImages: NewChatUserImagePayload[];
+			}
+		) => {
 			if (!threadId) {
 				toast.error("Cannot regenerate: no active chat thread");
 				return;
 			}
 
+			const isEdit = newUserQuery !== null;
+
 			// Abort any previous streaming request
 			if (abortControllerRef.current) {
 				abortControllerRef.current.abort();
@@ -1359,11 +1371,11 @@ export default function NewChatPage() {
 			}
 
 			// Extract the original user query BEFORE removing messages (for reload mode)
-			let userQueryToDisplay = newUserQuery;
+			let userQueryToDisplay: string | undefined;
 			let originalUserMessageContent: ThreadMessageLike["content"] | null = null;
 			let originalUserMessageMetadata: ThreadMessageLike["metadata"] | undefined;
 
-			if (!newUserQuery) {
+			if (!isEdit) {
 				// Reload mode - find and preserve the last user message content
 				const lastUserMessage = [...messages].reverse().find((m) => m.role === "user");
 				if (lastUserMessage) {
@@ -1377,6 +1389,8 @@ export default function NewChatPage() {
 						}
 					}
 				}
+			} else {
+				userQueryToDisplay = newUserQuery;
 			}
 
 			// Remove the last two messages (user + assistant) from the UI immediately
@@ -1412,11 +1426,13 @@ export default function NewChatPage() {
 			const userMessage: ThreadMessageLike = {
 				id: userMsgId,
 				role: "user",
-				content: newUserQuery
-					? [{ type: "text", text: newUserQuery }]
+				content: isEdit
+					? (editExtras?.userMessageContent ?? [
+							{ type: "text", text: newUserQuery ?? "" },
+						])
 					: originalUserMessageContent || [{ type: "text", text: userQueryToDisplay || "" }],
 				createdAt: new Date(),
-				metadata: newUserQuery ? undefined : originalUserMessageMetadata,
+				metadata: isEdit ? undefined : originalUserMessageMetadata,
 			};
 			setMessages((prev) => [...prev, userMessage]);
 
@@ -1433,20 +1449,24 @@ export default function NewChatPage() {
 
 			try {
 				const selection = await getAgentFilesystemSelection();
+				const requestBody: Record<string, unknown> = {
+					search_space_id: searchSpaceId,
+					user_query: newUserQuery,
+					disabled_tools: disabledTools.length > 0 ? disabledTools : undefined,
+					filesystem_mode: selection.filesystem_mode,
+					client_platform: selection.client_platform,
+					local_filesystem_mounts: selection.local_filesystem_mounts,
+				};
+				if (isEdit) {
+					requestBody.user_images = editExtras?.userImages ?? [];
+				}
 				const response = await fetch(getRegenerateUrl(threadId), {
 					method: "POST",
 					headers: {
 						"Content-Type": "application/json",
 						Authorization: `Bearer ${token}`,
 					},
-					body: JSON.stringify({
-						search_space_id: searchSpaceId,
-						user_query: newUserQuery || null,
-						disabled_tools: disabledTools.length > 0 ? disabledTools : undefined,
-						filesystem_mode: selection.filesystem_mode,
-						client_platform: selection.client_platform,
-						local_filesystem_mounts: selection.local_filesystem_mounts,
-					}),
+					body: JSON.stringify(requestBody),
 					signal: controller.signal,
 				});
 
@@ -1536,8 +1556,10 @@ export default function NewChatPage() {
 				if (contentParts.length > 0) {
 					try {
 						// Persist user message (for both edit and reload modes, since backend deleted it)
-						const userContentToPersist = newUserQuery
-							? [{ type: "text", text: newUserQuery }]
+						const userContentToPersist = isEdit
+							? (editExtras?.userMessageContent ?? [
+									{ type: "text", text: newUserQuery ?? "" },
+								])
 							: originalUserMessageContent || [{ type: "text", text: userQueryToDisplay || "" }];
 
 						const savedUserMessage = await appendMessage(threadId, {
@@ -1602,21 +1624,15 @@ export default function NewChatPage() {
 	// Handle editing a message - truncates history and regenerates with new query
 	const onEdit = useCallback(
 		async (message: AppendMessage) => {
-			// Extract the new user query from the message content
-			let newUserQuery = "";
-			for (const part of message.content) {
-				if (part.type === "text") {
-					newUserQuery += part.text;
-				}
-			}
-
-			if (!newUserQuery.trim()) {
+			const { userQuery, userImages } = extractUserTurnForNewChatApi(message, []);
+			const queryForApi = userQuery.trim();
+			if (!queryForApi && userImages.length === 0) {
 				toast.error("Cannot edit with empty message");
 				return;
 			}
 
-			// Call regenerate with the new query
-			await handleRegenerate(newUserQuery.trim());
+			const userMessageContent = message.content as unknown as ThreadMessageLike["content"];
+			await handleRegenerate(queryForApi, { userMessageContent, userImages });
 		},
 		[handleRegenerate]
 	);