diff --git a/src/core/assistant-message/presentAssistantMessage.ts b/src/core/assistant-message/presentAssistantMessage.ts
index ee3fa148b41..aa8dc4890bd 100644
--- a/src/core/assistant-message/presentAssistantMessage.ts
+++ b/src/core/assistant-message/presentAssistantMessage.ts
@@ -266,33 +266,46 @@ export async function presentAssistantMessage(cline: Task) {
 				progressStatus?: ToolProgressStatus,
 				isProtected?: boolean,
 			) => {
-				const { response, text, images } = await cline.ask(
-					type,
-					partialMessage,
-					false,
-					progressStatus,
-					isProtected || false,
-				)
+				try {
+					const { response, text, images } = await cline.ask(
+						type,
+						partialMessage,
+						false,
+						progressStatus,
+						isProtected || false,
+					)
+
+					if (response !== "yesButtonClicked") {
+						// Handle both messageResponse and noButtonClicked with text.
+						if (text) {
+							await cline.say("user_feedback", text, images)
+							pushToolResult(
+								formatResponse.toolResult(formatResponse.toolDeniedWithFeedback(text), images),
+							)
+						} else {
+							pushToolResult(formatResponse.toolDenied())
+						}
+						cline.didRejectTool = true
+						return false
+					}
 
-				if (response !== "yesButtonClicked") {
-					// Handle both messageResponse and noButtonClicked with text.
+					// Handle yesButtonClicked with text.
 					if (text) {
 						await cline.say("user_feedback", text, images)
-						pushToolResult(formatResponse.toolResult(formatResponse.toolDeniedWithFeedback(text), images))
-					} else {
-						pushToolResult(formatResponse.toolDenied())
+						pushToolResult(formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images))
 					}
-					cline.didRejectTool = true
-					return false
-				}
 
-				// Handle yesButtonClicked with text.
-				if (text) {
-					await cline.say("user_feedback", text, images)
-					pushToolResult(formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images))
-				}
+					return true
+				} catch (error) {
+					// Instead of silently returning false, properly handle the error
+					const errorMessage =
+						error instanceof Error ? error.message : "Unknown error occurred while processing command"
+					await cline.say("error", errorMessage)
 
-				return true
+					// Use parsingError for better clarity about what happened
+					pushToolResult(formatResponse.parsingError(errorMessage))
+					return false
+				}
 			}
 
 			const askFinishSubTaskApproval = async () => {
diff --git a/src/core/prompts/responses.ts b/src/core/prompts/responses.ts
index 3f38789fdc9..c29fca18407 100644
--- a/src/core/prompts/responses.ts
+++ b/src/core/prompts/responses.ts
@@ -15,6 +15,9 @@ export const formatResponse = {
 
 	toolError: (error?: string) => `The tool execution failed with the following error:\n<error>\n${error}\n</error>`,
 
+	parsingError: (error?: string) =>
+		`Failed to parse command or request:\n<error>\n${error}\n</error>\n\nThis error occurred before the approval dialog could be shown. Please check the command syntax and try again.`,
+
 	rooIgnoreError: (path: string) =>
 		`Access to ${path} is blocked by the .rooignore file settings. You must try to continue in the task without using this file, or ask the user to update the .rooignore file.`,