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fix: detect OAuth token expiry and show actionable error message #371

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fix: detect OAuth token expiry and show actionable error message #371

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59 changes: 55 additions & 4 deletions src/core/agent/ClaudianService.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -38,6 +38,7 @@ import {
buildContextFromHistory,
buildPromptWithHistoryContext,
getLastUserMessage,
isAuthenticationError,
isSessionExpiredError,
} from '../../utils/session';
import {
Expand Down Expand Up @@ -572,6 +573,12 @@ export class ClaudianService {
this.messageChannel.enqueue(messageToReplay);
return;
} catch (restartError) {
// If restart failed due to auth error, notify with actionable message
if (isAuthenticationError(restartError)) {
handler.onError(new Error('Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.'));
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
return;
}
// If restart failed due to session expiration, invalidate session
// so next query triggers noSessionButHasHistory → history rebuild
if (isSessionExpiredError(restartError)) {
Expand All @@ -584,6 +591,12 @@ export class ClaudianService {

// Notify active handler of error
if (handler) {
// Check if original error is an auth error — give actionable message
if (isAuthenticationError(errorInstance)) {
handler.onError(new Error('Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.'));
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
return;
}
handler.onError(errorInstance);
}

Expand All @@ -593,6 +606,11 @@ export class ClaudianService {
try {
await this.ensureReady({ force: true });
} catch (restartError) {
// If restart failed due to auth error, don't bother retrying
if (isAuthenticationError(restartError)) {
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
return;
}
// If restart failed due to session expiration, invalidate session
// so next query triggers noSessionButHasHistory → history rebuild
if (isSessionExpiredError(restartError)) {
Expand Down Expand Up @@ -811,6 +829,14 @@ export class ClaudianService {
yield* this.queryViaPersistent(promptToSend, images, vaultPath, resolvedClaudePath, effectiveQueryOptions);
return;
} catch (error) {
// Authentication errors are non-recoverable — don't retry
if (isAuthenticationError(error)) {
this.closePersistentQuery('authentication error');
yield { type: 'error', content: 'Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.' };
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
return;
}

if (isSessionExpiredError(error) && conversationHistory && conversationHistory.length > 0) {
this.sessionManager.invalidateSession();
const retryRequest = this.buildHistoryRebuildRequest(prompt, conversationHistory);
Expand All @@ -828,8 +854,13 @@ export class ClaudianService {
effectiveQueryOptions
);
} catch (retryError) {
const msg = retryError instanceof Error ? retryError.message : 'Unknown error';
yield { type: 'error', content: msg };
if (isAuthenticationError(retryError)) {
yield { type: 'error', content: 'Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.' };
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
} else {
const msg = retryError instanceof Error ? retryError.message : 'Unknown error';
yield { type: 'error', content: msg };
}
} finally {
this.coldStartInProgress = false;
this.abortController = null;
Expand All @@ -850,6 +881,13 @@ export class ClaudianService {
try {
yield* this.queryViaSDK(promptToSend, vaultPath, resolvedClaudePath, images, effectiveQueryOptions);
} catch (error) {
// Authentication errors are non-recoverable — don't retry
if (isAuthenticationError(error)) {
yield { type: 'error', content: 'Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.' };
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
return;
}

if (isSessionExpiredError(error) && conversationHistory && conversationHistory.length > 0) {
this.sessionManager.invalidateSession();
const retryRequest = this.buildHistoryRebuildRequest(prompt, conversationHistory);
Expand All @@ -864,8 +902,13 @@ export class ClaudianService {
effectiveQueryOptions
);
} catch (retryError) {
const msg = retryError instanceof Error ? retryError.message : 'Unknown error';
yield { type: 'error', content: msg };
if (isAuthenticationError(retryError)) {
yield { type: 'error', content: 'Authentication failed — your Claude OAuth token has expired. Please run `claude auth login` in your terminal to re-authenticate, then restart Claudian.' };
new Notice('Claude authentication expired. Run "claude auth login" in terminal to fix.', 10000);
} else {
const msg = retryError instanceof Error ? retryError.message : 'Unknown error';
yield { type: 'error', content: msg };
}
}
return;
}
Expand Down Expand Up @@ -1025,6 +1068,10 @@ export class ClaudianService {

// Check if an error occurred (assigned in onError callback)
if (state.error) {
// Re-throw authentication errors for outer handling (non-recoverable)
if (isAuthenticationError(state.error)) {
throw state.error;
}
// Re-throw session expired errors for outer retry logic to handle
if (isSessionExpiredError(state.error)) {
throw state.error;
Expand Down Expand Up @@ -1329,6 +1376,10 @@ export class ClaudianService {
}
}
} catch (error) {
// Re-throw authentication errors (non-recoverable)
if (isAuthenticationError(error)) {
throw error;
}
// Re-throw session expired errors for outer retry logic to handle
if (isSessionExpiredError(error)) {
throw error;
Expand Down
52 changes: 52 additions & 0 deletions src/utils/session.ts
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Original file line number Diff line number Diff line change
Expand Up @@ -43,6 +43,58 @@ export function isSessionExpiredError(error: unknown): boolean {
return false;
}

// ============================================
// Authentication Error Detection
// ============================================

const AUTH_ERROR_PATTERNS = [
'authentication_failed',
'authentication_error',
'oauth token has expired',
'failed to authenticate',
'obtain a new token',
'refresh your existing token',
'invalid api key',
'invalid x-api-key',
'api key not found',
] as const;

const AUTH_ERROR_COMPOUND_PATTERNS = [
{ includes: ['401', 'authentication'] },
{ includes: ['token', 'expired'] },
{ includes: ['oauth', 'expired'] },
] as const;

/**
* Detects authentication/OAuth errors from the Claude API.
* These are distinct from session expiry — retrying won't help
* because the underlying credentials are invalid.
*/
export function isAuthenticationError(error: unknown): boolean {
let msg = '';
if (error instanceof Error) {
msg = error.message.toLowerCase();
} else if (typeof error === 'string') {
msg = error.toLowerCase();
}

if (!msg) return false;

for (const pattern of AUTH_ERROR_PATTERNS) {
if (msg.includes(pattern)) {
return true;
}
}

for (const { includes } of AUTH_ERROR_COMPOUND_PATTERNS) {
if (includes.every(part => msg.includes(part))) {
return true;
}
}

return false;
}

// ============================================
// History Reconstruction
// ============================================
Expand Down
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