diff --git a/packages/cli/src/ActiveWorkflowRunner.ts b/packages/cli/src/ActiveWorkflowRunner.ts
index 66d4ec02e2..be77bd101f 100644
--- a/packages/cli/src/ActiveWorkflowRunner.ts
+++ b/packages/cli/src/ActiveWorkflowRunner.ts
@@ -39,6 +39,8 @@ import {
 	LoggerProxy as Logger,
 } from 'n8n-workflow';
 
+const WEBHOOK_PROD_UNREGISTERED_HINT = `The workflow must be active for a production URL to run successfully. You can activate the workflow using the toggle in the top-right of the editor. Note that unlike test URL calls, production URL calls aren't shown on the canvas (only in the executions list)`;
+
 export class ActiveWorkflowRunner {
 	private activeWorkflows: ActiveWorkflows | null = null;
 
@@ -148,7 +150,7 @@ export class ActiveWorkflowRunner {
 			const dynamicWebhooks = await Db.collections.Webhook?.find({ webhookId, method: httpMethod, pathLength: pathElements.length });
 			if (dynamicWebhooks === undefined || dynamicWebhooks.length === 0) {
 				// The requested webhook is not registered
-				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404);
+				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404, WEBHOOK_PROD_UNREGISTERED_HINT);
 			}
 
 			let maxMatches = 0;
@@ -169,7 +171,7 @@ export class ActiveWorkflowRunner {
 				}
 			});
 			if (webhook === undefined) {
-				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404);
+				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404, WEBHOOK_PROD_UNREGISTERED_HINT);
 			}
 
 			path = webhook!.webhookPath;
diff --git a/packages/cli/src/ResponseHelper.ts b/packages/cli/src/ResponseHelper.ts
index 465fdb5dde..24a9d37b53 100644
--- a/packages/cli/src/ResponseHelper.ts
+++ b/packages/cli/src/ResponseHelper.ts
@@ -21,17 +21,21 @@ export class ResponseError extends Error {
 	// The HTTP status code of  response
 	httpStatusCode?: number;
 
-	// The error code in the resonse
+	// The error code in the response
 	errorCode?: number;
 
+	// The error hint the response
+	hint?: string;
+
 	/**
 	 * Creates an instance of ResponseError.
 	 * @param {string} message The error message
 	 * @param {number} [errorCode] The error code which can be used by frontend to identify the actual error
 	 * @param {number} [httpStatusCode] The HTTP status code the response should have
+	 * @param {string} [hint] The error hint to provide a context (webhook related)
 	 * @memberof ResponseError
 	 */
-	constructor(message: string, errorCode?: number, httpStatusCode?: number) {
+	constructor(message: string, errorCode?: number, httpStatusCode?: number, hint?:string) {
 		super(message);
 		this.name = 'ResponseError';
 
@@ -41,6 +45,9 @@ export class ResponseError extends Error {
 		if (httpStatusCode) {
 			this.httpStatusCode = httpStatusCode;
 		}
+		if (hint) {
+			this.hint = hint;
+		}
 	}
 }
 
@@ -91,6 +98,7 @@ export function sendErrorResponse(res: Response, error: ResponseError) {
 	const response = {
 		code: 0,
 		message: 'Unknown error',
+		hint: '',
 	};
 
 	if (error.name === 'NodeApiError') {
@@ -103,6 +111,9 @@ export function sendErrorResponse(res: Response, error: ResponseError) {
 	if (error.message) {
 		response.message = error.message;
 	}
+	if (error.hint) {
+		response.hint = error.hint;
+	}
 	if (error.stack && process.env.NODE_ENV !== 'production') {
 		// @ts-ignore
 		response.stack = error.stack;
diff --git a/packages/cli/src/TestWebhooks.ts b/packages/cli/src/TestWebhooks.ts
index b9dcf09fcb..a8aa17720f 100644
--- a/packages/cli/src/TestWebhooks.ts
+++ b/packages/cli/src/TestWebhooks.ts
@@ -21,7 +21,7 @@ import {
 	WorkflowExecuteMode,
 } from 'n8n-workflow';
 
-
+const WEBHOOK_TEST_UNREGISTERED_HINT = `Click the 'Execute workflow' button on the canvas, then try again. (In test mode, the webhook only works for one call after you click this button)`;
 
 export class TestWebhooks {
 
@@ -72,7 +72,7 @@ export class TestWebhooks {
 			webhookData = this.activeWebhooks!.get(httpMethod, pathElements.join('/'), webhookId);
 			if (webhookData === undefined) {
 				// The requested webhook is not registered
-				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404);
+				throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404, WEBHOOK_TEST_UNREGISTERED_HINT);
 			}
 
 			path = webhookData.path;
@@ -90,7 +90,7 @@ export class TestWebhooks {
 		// TODO: Clean that duplication up one day and improve code generally
 		if (this.testWebhookData[webhookKey] === undefined) {
 			// The requested webhook is not registered
-			throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404);
+			throw new ResponseHelper.ResponseError(`The requested webhook "${httpMethod} ${path}" is not registered.`, 404, 404, WEBHOOK_TEST_UNREGISTERED_HINT);
 		}
 
 		const workflow = this.testWebhookData[webhookKey].workflow;
@@ -145,7 +145,7 @@ export class TestWebhooks {
 
 		if (webhookMethods === undefined) {
 			// The requested webhook is not registered
-			throw new ResponseHelper.ResponseError(`The requested webhook "${path}" is not registered.`, 404, 404);
+			throw new ResponseHelper.ResponseError(`The requested webhook "${path}" is not registered.`, 404, 404, WEBHOOK_TEST_UNREGISTERED_HINT);
 		}
 
 		return webhookMethods;