// chris johnsonField notes on cybersecurity, AI-assisted development, infrastructure, and the craft of shipping things that actually work.
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My Gmail assistant ran clean for two months, then quietly died for a full week before I noticed. The bridge daemon that drove it had pinned itself to a stale Claude CLI version, every scheduled fire failed within seconds, and no transcript was ever written. This post walks through why I migrated the agent off Claude Routines and onto the Claude Agent SDK, what the new stack looks like on launchd, and the parity gate that has to pass before the old agent gets decommissioned.
Building a Gmail cleanup agent in Claude Code, evolving it from a manual 5-step script to a fully autonomous v3 with VIP detection, delta sync, auto-labeling, and follow-up tracking. Then making it run unattended every 5 hours via scheduled triggers and a remote-control daemon on a Mac Mini.