From 71ca931188d2b96d18ad9ce16123ea00f4e5338c Mon Sep 17 00:00:00 2001
From: Michael Drury <me@michaeldrury.co.uk>
Date: Tue, 13 Jan 2026 13:27:40 +0000
Subject: [PATCH] fix(ai-builder): Long running prompts throw internal 401
 error rather than expected complexity error (#24114)

---
 .../src/test/workflow-builder-agent.test.ts   | 47 ++++++++++++++++++-
 .../src/workflow-builder-agent.ts             | 33 +++++++++++--
 2 files changed, 75 insertions(+), 5 deletions(-)

diff --git a/packages/@n8n/ai-workflow-builder.ee/src/test/workflow-builder-agent.test.ts b/packages/@n8n/ai-workflow-builder.ee/src/test/workflow-builder-agent.test.ts
index 78e38a0f56f..9b95628c5fa 100644
--- a/packages/@n8n/ai-workflow-builder.ee/src/test/workflow-builder-agent.test.ts
+++ b/packages/@n8n/ai-workflow-builder.ee/src/test/workflow-builder-agent.test.ts
@@ -197,6 +197,43 @@ describe('WorkflowBuilderAgent', () => {
 			}).rejects.toThrow(ApplicationError);
 		});
 
+		it('should handle 401 expired token error from LangChain MODEL_AUTHENTICATION', async () => {
+			// This matches the actual error structure from LangChain when the AI assistant proxy token expires
+			const expiredTokenError = Object.assign(new Error('Expired token'), {
+				status: 401,
+				lc_error_code: 'MODEL_AUTHENTICATION',
+			});
+
+			mockCreateStreamProcessor.mockImplementation(() => {
+				// eslint-disable-next-line require-yield
+				return (async function* () {
+					throw expiredTokenError;
+				})();
+			});
+
+			await expect(async () => {
+				const generator = agent.chat(mockPayload);
+				await generator.next();
+			}).rejects.toThrow(ApplicationError);
+		});
+
+		it('should not treat generic 401 errors as expired token errors', async () => {
+			// A generic 401 without lc_error_code should be rethrown as-is, not converted to ApplicationError
+			const generic401Error = Object.assign(new Error('Unauthorized'), { status: 401 });
+
+			mockCreateStreamProcessor.mockImplementation(() => {
+				// eslint-disable-next-line require-yield
+				return (async function* () {
+					throw generic401Error;
+				})();
+			});
+
+			await expect(async () => {
+				const generator = agent.chat(mockPayload);
+				await generator.next();
+			}).rejects.toThrow(generic401Error);
+		});
+
 		it('should handle invalid request errors', async () => {
 			const invalidRequestError = Object.assign(new Error('Request failed'), {
 				error: {
@@ -207,12 +244,18 @@ describe('WorkflowBuilderAgent', () => {
 				},
 			});
 
-			(mockLlmSimple.invoke as jest.Mock).mockRejectedValue(invalidRequestError);
+			// Mock the stream processor to throw the invalid request error
+			mockCreateStreamProcessor.mockImplementation(() => {
+				// eslint-disable-next-line require-yield
+				return (async function* () {
+					throw invalidRequestError;
+				})();
+			});
 
 			await expect(async () => {
 				const generator = agent.chat(mockPayload);
 				await generator.next();
-			}).rejects.toThrow(ApplicationError);
+			}).rejects.toThrow(ValidationError);
 		});
 
 		it('should rethrow unknown errors', async () => {
diff --git a/packages/@n8n/ai-workflow-builder.ee/src/workflow-builder-agent.ts b/packages/@n8n/ai-workflow-builder.ee/src/workflow-builder-agent.ts
index 3f3ce29a2da..346e1899f7d 100644
--- a/packages/@n8n/ai-workflow-builder.ee/src/workflow-builder-agent.ts
+++ b/packages/@n8n/ai-workflow-builder.ee/src/workflow-builder-agent.ts
@@ -27,6 +27,9 @@ import type { WorkflowState } from './workflow-state';
 const PROMPT_IS_TOO_LARGE_ERROR =
 	'The current conversation and workflow state is too large to process. Try to simplify your workflow by breaking it into smaller parts.';
 
+const WORKFLOW_TOO_COMPLEX_ERROR =
+	'Workflow generation stopped: The AI reached the maximum number of steps while building your workflow. This usually means the workflow design became too complex or got stuck in a loop while trying to create the nodes and connections.';
+
 /**
  * Type for the state snapshot with properly typed values
  */
@@ -283,15 +286,39 @@ export class WorkflowBuilderAgent {
 
 		// If it's not an abort error, check for GraphRecursionError
 		if (error instanceof GraphRecursionError) {
-			throw new ApplicationError(
-				'Workflow generation stopped: The AI reached the maximum number of steps while building your workflow. This usually means the workflow design became too complex or got stuck in a loop while trying to create the nodes and connections.',
-			);
+			throw new ApplicationError(WORKFLOW_TOO_COMPLEX_ERROR);
+		}
+
+		// Check for 401 expired token errors (typically from long-running generations)
+		if (this.isTokenExpiredError(error)) {
+			throw new ApplicationError(WORKFLOW_TOO_COMPLEX_ERROR);
 		}
 
 		// Re-throw any other errors
 		throw error;
 	}
 
+	/**
+	 * Checks if the error is a 401 expired token error from the LLM provider proxy.
+	 * This typically occurs during very long-running workflow generations when
+	 * the AI assistant service proxy token expires.
+	 *
+	 * We specifically check for LangChain's MODEL_AUTHENTICATION error code to ensure
+	 * we only catch authentication errors from the LLM provider, not unrelated 401s.
+	 */
+	private isTokenExpiredError(error: unknown): boolean {
+		const LC_MODEL_AUTHENTICATION_ERROR = 'MODEL_AUTHENTICATION';
+
+		return (
+			!!error &&
+			typeof error === 'object' &&
+			'lc_error_code' in error &&
+			error.lc_error_code === LC_MODEL_AUTHENTICATION_ERROR &&
+			'status' in error &&
+			error.status === 401
+		);
+	}
+
 	private getInvalidRequestError(error: unknown): string | undefined {
 		if (
 			error instanceof Error &&