fix: improve Claude Code authentication error handling

src/api/providers/__tests__/claude-code.spec.ts

@@ -1,18 +1,32 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
 import { ClaudeCodeHandler } from "../claude-code"
 import { ApiHandlerOptions } from "../../../shared/api"
 import { ClaudeCodeMessage } from "../../../integrations/claude-code/types"
+import { runClaudeCode } from "../../../integrations/claude-code/run"
+import { t } from "../../../i18n"
 
 // Mock the runClaudeCode function
 vi.mock("../../../integrations/claude-code/run", () => ({
 	runClaudeCode: vi.fn(),
 }))
 
+vi.mock("../../../i18n", () => ({
+	t: vi.fn((key: string, options?: any) => {
+		if (key === "common:errors.claudeCode.authenticationError") {
+			return `Claude Code authentication failed. Original error: ${options?.originalError || "unknown"}`
+		}
+		if (key === "common:errors.claudeCode.apiKeyModelPlanMismatch") {
+			return "API keys and subscription plans allow different models. Make sure the selected model is included in your plan."
+		}
+		return key
+	}),
+}))
+
 // Mock the message filter
 vi.mock("../../../integrations/claude-code/message-filter", () => ({
 	filterMessagesForClaudeCode: vi.fn((messages) => messages),
 }))
 
-const { runClaudeCode } = await import("../../../integrations/claude-code/run")
 const { filterMessagesForClaudeCode } = await import("../../../integrations/claude-code/message-filter")
 const mockRunClaudeCode = vi.mocked(runClaudeCode)
 const mockFilterMessages = vi.mocked(filterMessagesForClaudeCode)
@@ -563,3 +577,151 @@ describe("ClaudeCodeHandler", () => {
 		consoleSpy.mockRestore()
 	})
 })
+
+describe("ClaudeCodeHandler Authentication Error Handling", () => {
+	let handler: ClaudeCodeHandler
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+		handler = new ClaudeCodeHandler({
+			claudeCodePath: "claude",
+			apiModelId: "claude-3-5-sonnet-20241022",
+		} as ApiHandlerOptions)
+	})
+
+	afterEach(() => {
+		vi.clearAllMocks()
+	})
+
+	it("should detect and handle authentication errors from API response", async () => {
+		const mockGenerator = async function* (): AsyncGenerator<ClaudeCodeMessage | string> {
+			yield {
+				type: "assistant" as const,
+				message: {
+					id: "msg_123",
+					type: "message",
+					role: "assistant",
+					model: "claude-3-5-sonnet-20241022",
+					content: [
+						{
+							type: "text",
+							text: 'API Error: 401 {"error":{"message":"Authentication failed. Please login with claude login"}}',
+						},
+					],
+					stop_reason: "stop",
+					stop_sequence: null,
+					usage: {
+						input_tokens: 100,
+						output_tokens: 50,
+						cache_read_input_tokens: 0,
+						cache_creation_input_tokens: 0,
+					},
+				} as any,
+				session_id: "session_123",
+			}
+		}
+
+		mockRunClaudeCode.mockReturnValue(mockGenerator())
+
+		const messages: any[] = [{ role: "user", content: "test" }]
+		const generator = handler.createMessage("system", messages)
+
+		await expect(async () => {
+			for await (const _ of generator) {
+				// consume generator
+			}
+		}).rejects.toThrow("Claude Code authentication failed")
+	})
+
+	it("should detect various authentication error patterns", async () => {
+		const authErrorMessages = [
+			"API Error: 403 Unauthorized",
+			"API Error: Invalid API key",
+			"API Error: Credential expired",
+			"API Error: Login required",
+			"API Error: Not authenticated",
+		]
+
+		for (const errorMessage of authErrorMessages) {
+			const mockGenerator = async function* (): AsyncGenerator<ClaudeCodeMessage | string> {
+				yield {
+					type: "assistant" as const,
+					message: {
+						id: "msg_123",
+						type: "message",
+						role: "assistant",
+						model: "claude-3-5-sonnet-20241022",
+						content: [
+							{
+								type: "text",
+								text: errorMessage,
+							},
+						],
+						stop_reason: "stop",
+						stop_sequence: null,
+						usage: {
+							input_tokens: 100,
+							output_tokens: 50,
+							cache_read_input_tokens: 0,
+							cache_creation_input_tokens: 0,
+						},
+					} as any,
+					session_id: "session_123",
+				}
+			}
+
+			mockRunClaudeCode.mockReturnValue(mockGenerator())
+
+			const messages: any[] = [{ role: "user", content: "test" }]
+			const generator = handler.createMessage("system", messages)
+
+			await expect(async () => {
+				for await (const _ of generator) {
+					// consume generator
+				}
+			}).rejects.toThrow("Claude Code authentication failed")
+
+			vi.clearAllMocks()
+		}
+	})
+
+	it("should not treat non-authentication errors as authentication errors", async () => {
+		const mockGenerator = async function* (): AsyncGenerator<ClaudeCodeMessage | string> {
+			yield {
+				type: "assistant" as const,
+				message: {
+					id: "msg_123",
+					type: "message",
+					role: "assistant",
+					model: "claude-3-5-sonnet-20241022",
+					content: [
+						{
+							type: "text",
+							text: "API Error: 500 Internal Server Error",
+						},
+					],
+					stop_reason: "stop",
+					stop_sequence: null,
+					usage: {
+						input_tokens: 100,
+						output_tokens: 50,
+						cache_read_input_tokens: 0,
+						cache_creation_input_tokens: 0,
+					},
+				} as any,
+				session_id: "session_123",
+			}
+		}
+
+		mockRunClaudeCode.mockReturnValue(mockGenerator())
+
+		const messages: any[] = [{ role: "user", content: "test" }]
+		const generator = handler.createMessage("system", messages)
+
+		await expect(async () => {
+			for await (const _ of generator) {
+				// consume generator
+			}
+		}).rejects.toThrow("API Error: 500 Internal Server Error")
+	})
+})

src/api/providers/claude-code.ts

@@ -82,9 +82,26 @@ export class ClaudeCodeHandler extends BaseProvider implements ApiHandler {
 
 						const error = this.attemptParse(errorMessage)
 						if (!error) {
+							// Check for authentication errors in raw message
+							if (this.isAuthenticationError(content.text)) {
+								throw new Error(
+									t("common:errors.claudeCode.authenticationError", {
+										originalError: content.text,
+									}),
+								)
+							}
 							throw new Error(content.text)
 						}
 
+						// Check for authentication-related errors
+						if (this.isAuthenticationError(error.error?.message || errorMessage)) {
+							throw new Error(
+								t("common:errors.claudeCode.authenticationError", {
+									originalError: error.error?.message || errorMessage,
+								}),
+							)
+						}
+
 						if (error.error.message.includes("Invalid model name")) {
 							throw new Error(
 								content.text + `\n\n${t("common:errors.claudeCode.apiKeyModelPlanMismatch")}`,
@@ -172,4 +189,22 @@ export class ClaudeCodeHandler extends BaseProvider implements ApiHandler {
 			return null
 		}
 	}
+
+	private isAuthenticationError(message: string): boolean {
+		const authErrorPatterns = [
+			"authentication failed",
+			"unauthorized",
+			"not authenticated",
+			"login required",
+			"invalid api key",
+			"api key expired",
+			"credential",
+			"auth error",
+			"403",
+			"401",
+		]
+
+		const lowerMessage = message.toLowerCase()
+		return authErrorPatterns.some((pattern) => lowerMessage.includes(pattern))
+	}
 }

src/i18n/locales/en/common.json

@@ -92,7 +92,8 @@
 			"processExitedWithError": "Claude Code process exited with code {{exitCode}}. Error output: {{output}}",
 			"stoppedWithReason": "Claude Code stopped with reason: {{reason}}",
 			"apiKeyModelPlanMismatch": "API keys and subscription plans allow different models. Make sure the selected model is included in your plan.",
-			"notFound": "Claude Code executable '{{claudePath}}' not found.\n\nPlease install Claude Code CLI:\n1. Visit {{installationUrl}} to download Claude Code\n2. Follow the installation instructions for your operating system\n3. Ensure the 'claude' command is available in your PATH\n4. Alternatively, configure a custom path in Roo settings under 'Claude Code Path'\n\nOriginal error: {{originalError}}"
+			"notFound": "Claude Code executable '{{claudePath}}' not found.\n\nPlease install Claude Code CLI:\n1. Visit {{installationUrl}} to download Claude Code\n2. Follow the installation instructions for your operating system\n3. Ensure the 'claude' command is available in your PATH\n4. Alternatively, configure a custom path in Roo settings under 'Claude Code Path'\n\nOriginal error: {{originalError}}",
+			"authenticationError": "Claude Code authentication failed.\n\nTo authenticate with Claude Code CLI:\n1. Open a terminal/command prompt\n2. Run: claude login\n3. Follow the authentication prompts in your browser\n4. Once authenticated, try again in VS Code\n\nIf you're still having issues:\n• Ensure you're using Claude Code CLI v2.0.30 or later\n• Try running: claude logout && claude login\n• Check if your API key has expired at https://console.anthropic.com\n\nOriginal error: {{originalError}}"
 		},
 		"message": {
 			"no_active_task_to_delete": "No active task to delete messages from",

src/integrations/claude-code/run.ts

@@ -108,6 +108,16 @@ export async function* runClaudeCode(
 			}
 
 			const errorOutput = (processState.error as any)?.message || processState.stderrLogs?.trim()
+
+			// Check for authentication errors in stderr or error output
+			if (errorOutput && isAuthenticationError(errorOutput)) {
+				throw new Error(
+					t("common:errors.claudeCode.authenticationError", {
+						originalError: errorOutput,
+					}),
+				)
+			}
+
 			throw new Error(
 				`Claude Code process exited with code ${exitCode}.${errorOutput ? ` Error output: ${errorOutput}` : ""}`,
 			)
@@ -273,3 +283,26 @@ function createClaudeCodeNotFoundError(claudePath: string, originalError: Error)
 	error.name = "ClaudeCodeNotFoundError"
 	return error
 }
+
+/**
+ * Checks if an error message indicates an authentication issue
+ */
+function isAuthenticationError(message: string): boolean {
+	const authErrorPatterns = [
+		"authentication failed",
+		"unauthorized",
+		"not authenticated",
+		"login required",
+		"invalid api key",
+		"api key expired",
+		"credential",
+		"auth error",
+		"403",
+		"401",
+		"please authenticate",
+		"claude login",
+	]
+
+	const lowerMessage = message.toLowerCase()
+	return authErrorPatterns.some((pattern) => lowerMessage.includes(pattern))
+}