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Custom connector doesn't prompt reauth when OAuth token expires — silently loses tool access #702

Description

@dhaskell

When a custom MCP connector's OAuth access token expires, the server correctly returns 401 with a WWW-Authenticate header pointing to /.well-known/oauth-protected-resource (per the MCP auth spec). Claude doesn't act on this signal — the tool silently disappears from the conversation with no reauth prompt and no visible error explaining why. The only fix is manually going to Settings → Connectors and disconnecting/reconnecting the connector.

Expected: Claude should either automatically redo the OAuth flow using the discovered protected-resource metadata, or at minimum surface a "this connector needs reauthorization" prompt to the user instead of failing silently.

This matches a known limitation referenced in third-party MCP server docs ("some clients including the Claude app and Claude Code do not yet auto re-initialize on a 404 and require a manual reconnect").

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