diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 6231f081670..b70b9ac23bf 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -115,6 +115,7 @@ export class ClineProvider
 	public readonly latestAnnouncementId = "jul-09-2025-3-23-0" // Update for v3.23.0 announcement
 	public readonly providerSettingsManager: ProviderSettingsManager
 	public readonly customModesManager: CustomModesManager
+	public hasShownEditWarning = false // Session-based flag for edit warning dialog
 
 	constructor(
 		readonly context: vscode.ExtensionContext,
diff --git a/src/core/webview/__tests__/ClineProvider.spec.ts b/src/core/webview/__tests__/ClineProvider.spec.ts
index 5272c334510..51384422ccf 100644
--- a/src/core/webview/__tests__/ClineProvider.spec.ts
+++ b/src/core/webview/__tests__/ClineProvider.spec.ts
@@ -2909,21 +2909,24 @@ describe("ClineProvider - Comprehensive Edit/Delete Edge Cases", () => {
 
 			await Promise.all([edit1Promise, edit2Promise])
 
-			// Verify dialogs were shown for both edits
+			// With the new implementation, only the first edit shows the dialog
+			// The second edit happens after hasShownEditWarning is already true
 			expect(mockPostMessage).toHaveBeenCalledWith({
 				type: "showEditMessageDialog",
 				messageTs: 2000,
 				text: "Edited message 1",
+				images: undefined,
 			})
-			expect(mockPostMessage).toHaveBeenCalledWith({
+
+			// The second edit should not show a dialog
+			expect(mockPostMessage).not.toHaveBeenCalledWith({
 				type: "showEditMessageDialog",
 				messageTs: 4000,
 				text: "Edited message 2",
 			})
 
-			// Simulate user confirming both edits
+			// Simulate user confirming the first edit
 			await messageHandler({ type: "editMessageConfirm", messageTs: 2000, text: "Edited message 1" })
-			await messageHandler({ type: "editMessageConfirm", messageTs: 4000, text: "Edited message 2" })
 
 			// Both operations should complete without throwing
 			expect(mockCline.overwriteClineMessages).toHaveBeenCalled()
diff --git a/src/core/webview/__tests__/webviewMessageHandler.spec.ts b/src/core/webview/__tests__/webviewMessageHandler.spec.ts
index 284ee989444..2c40d92e17b 100644
--- a/src/core/webview/__tests__/webviewMessageHandler.spec.ts
+++ b/src/core/webview/__tests__/webviewMessageHandler.spec.ts
@@ -517,8 +517,9 @@ describe("webviewMessageHandler - message dialog preferences", () => {
 	})
 
 	describe("submitEditedMessage", () => {
-		it("should always show dialog for edit confirmation", async () => {
+		it("should show dialog for edit confirmation on first edit in session", async () => {
 			vi.mocked(mockClineProvider.getCurrentCline).mockReturnValue({} as any) // Mock current cline exists
+			mockClineProvider.hasShownEditWarning = false // Reset the flag
 
 			await webviewMessageHandler(mockClineProvider, {
 				type: "submitEditedMessage",
@@ -531,6 +532,75 @@ describe("webviewMessageHandler - message dialog preferences", () => {
 				messageTs: 123456789,
 				text: "edited content",
 			})
+			expect(mockClineProvider.hasShownEditWarning).toBe(true)
+		})
+
+		it("should not show dialog for subsequent edits in the same session", async () => {
+			const editMessageTs = 1234567890000 // Message to edit
+			const mockCline = {
+				taskId: "test-task-id",
+				apiConversationHistory: [
+					{ role: "user", content: "Previous message", ts: editMessageTs - 5000 },
+					{ role: "assistant", content: "Response", ts: editMessageTs - 4000 },
+					{ role: "user", content: "Message to edit", ts: editMessageTs },
+					{ role: "assistant", content: "Later response", ts: editMessageTs + 2000 },
+				],
+				clineMessages: [
+					{ ts: editMessageTs - 5000, type: "say", say: "text", text: "Much earlier message" },
+					{ ts: editMessageTs - 2000, type: "say", say: "text", text: "Earlier message" },
+					{ ts: editMessageTs, type: "say", say: "user_feedback", text: "Original message to edit" },
+					{ ts: editMessageTs + 2000, type: "say", say: "text", text: "Later message" },
+				],
+				overwriteClineMessages: vi.fn().mockResolvedValue(undefined),
+				overwriteApiConversationHistory: vi.fn().mockResolvedValue(undefined),
+				handleWebviewAskResponse: vi.fn(),
+			}
+
+			// Mock getCurrentCline to always return our mockCline
+			vi.mocked(mockClineProvider.getCurrentCline).mockReturnValue(mockCline as any)
+
+			vi.mocked(mockClineProvider.getTaskWithId).mockResolvedValue({
+				historyItem: { id: "test-task-id" } as any,
+				taskDirPath: "/test/path",
+				apiConversationHistoryFilePath: "/test/path/api.json",
+				uiMessagesFilePath: "/test/path/ui.json",
+				apiConversationHistory: [],
+			})
+			vi.mocked(mockClineProvider.initClineWithHistoryItem).mockResolvedValue({} as any)
+
+			mockClineProvider.hasShownEditWarning = true // Flag already set from previous edit
+
+			await webviewMessageHandler(mockClineProvider, {
+				type: "submitEditedMessage",
+				value: editMessageTs,
+				editedMessageContent: "edited content",
+				images: undefined,
+			})
+
+			// Should not show dialog
+			expect(mockClineProvider.postMessageToWebview).not.toHaveBeenCalledWith({
+				type: "showEditMessageDialog",
+				messageTs: editMessageTs,
+				text: "edited content",
+			})
+
+			// Should have called overwrite methods to remove messages from the timestamp onwards
+			// The cutoff is editMessageTs - 1000, so messages before that should remain
+			expect(mockCline.overwriteClineMessages).toHaveBeenCalledWith([
+				{ ts: editMessageTs - 5000, type: "say", say: "text", text: "Much earlier message" },
+				{ ts: editMessageTs - 2000, type: "say", say: "text", text: "Earlier message" },
+			])
+			expect(mockCline.overwriteApiConversationHistory).toHaveBeenCalledWith([
+				{ role: "user", content: "Previous message", ts: editMessageTs - 5000 },
+				{ role: "assistant", content: "Response", ts: editMessageTs - 4000 },
+			])
+
+			// Should have called handleWebviewAskResponse
+			expect(mockCline.handleWebviewAskResponse).toHaveBeenCalledWith(
+				"messageResponse",
+				"edited content",
+				undefined,
+			)
 		})
 	})
 })
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 780d40df891..38aa965477f 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -138,13 +138,20 @@ export const webviewMessageHandler = async (
 	 * Handles message editing operations with user confirmation
 	 */
 	const handleEditOperation = async (messageTs: number, editedContent: string, images?: string[]): Promise<void> => {
-		// Send message to webview to show edit confirmation dialog
-		await provider.postMessageToWebview({
-			type: "showEditMessageDialog",
-			messageTs,
-			text: editedContent,
-			images,
-		})
+		// Check if we've already shown the edit warning in this session
+		if (!provider.hasShownEditWarning) {
+			// First time editing in this session - show the warning dialog
+			provider.hasShownEditWarning = true
+			await provider.postMessageToWebview({
+				type: "showEditMessageDialog",
+				messageTs,
+				text: editedContent,
+				images,
+			})
+		} else {
+			// Already shown the warning in this session - proceed directly with the edit
+			await handleEditMessageConfirm(messageTs, editedContent, images)
+		}
 	}
 
 	/**