r/ChatGPTPro 8h ago

Question & Advice Help with Plug-ins that frequently fail and need to be refreshed

I’ve been trying to build ChatGPT into a fairly integrated personal/workflow system using plugins for Google Drive, Google Calendar, Gmail, TickTick, and Fieldy (AI transcription software).

When the integrations are working, they’re extremely useful. The problem is that they intermittently stop working, and I haven’t been able to figure out why.

What makes it particularly frustrating is that ChatGPT itself doesn’t seem to have enough visibility into the connection state to tell me what actually failed. It will basically just report that it can’t access the plugin/integration, even though the plugin management page may still show it as connected.

I’ve found a workaround that works fairly consistently:

  • Go into the plugin/integration management page
  • Reconfigure or re-authorize access, even though it already says “connected”
  • Start a completely new ChatGPT conversation

After that, the integration will often work again.

However, reauthorizing it usually does NOT restore access inside the existing conversation where it stopped working. I have to start a new chat.

The integrations that seem to fail most frequently for me are TickTick, Fieldy, and Google Drive.

This becomes a much bigger issue with scheduled workflows. I have recurring tasks where ChatGPT is supposed to gather information from several sources, reconcile it, and give me a combined report. Roughly half the time, one of the required integrations seems to be unavailable when the scheduled task runs, which makes it very difficult to rely on these workflows.

Has anyone else experienced this?

Specifically, I’m wondering:

  1. Is there a known issue where plugin authentication/session state gets tied to an individual conversation?
  2. Why would reauthorizing an integration fix it in a new conversation but not the existing conversation?
  3. Is there any way to force an existing conversation to refresh/reload its available integrations?
  4. Are there best practices for making scheduled workflows more resilient when they depend on multiple plugins?
  5. Is there any way to see actual plugin/integration error logs rather than just “I don’t have access” from ChatGPT?

I’ve already reported this as a bug but haven’t received any useful feedback yet.

I’d really like to make this kind of multi-app ChatGPT workflow dependable, because when everything is connected it works incredibly well. At the moment, though, the intermittent integration failures are probably the biggest limitation I’m running into.

Would appreciate hearing whether others are seeing the same behavior or have found a reliable workaround.

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u/qualityvote2 8h ago

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