ChatGPT plugins silently fail; re-auth works only in a brand-new conversation

Kaboose31 · reddit · 2026-09-09

A user wired ChatGPT into Google Drive/Calendar, Gmail, TickTick and Fieldy via plugins, but integrations intermittently break: ChatGPT only says it can't access the plugin while the management page still shows "connected," with no visibility into the actual failure.

A fairly consistent workaround: re-authorize the integration in the plugin management page, then start a completely new conversation — re-authorizing usually does NOT restore access inside the conversation where it broke. TickTick, Fieldy and Google Drive fail most often.

This hits scheduled workflows hardest: roughly half the time one required integration is unavailable when the scheduled task runs, making multi-source report workflows unreliable. Open questions: is plugin auth/session state tied to individual conversations, and how to get real plugin error logs?

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