Operator Problem Guide
Scheduling Software Keeps Disconnecting — Why It Happens & How to Fix It
Quick Answer
Scheduling software keeps disconnecting because of one of three root causes:
- Auth token expiry — OAuth tokens expire and the software loses permission to your calendar or third-party service. Fix: re-authorize the connection in your integration settings.
- API rate limits — too many sync requests hitting the vendor's API, causing the connection to be throttled or dropped. Fix: increase sync intervals or upgrade your plan tier.
- Webhook misconfiguration — the receiving URL changed, SSL expired, or the endpoint stopped responding. Fix: check the webhook URL is still live and returning 200.
Which one is it? Check in this order
- Go to your integration settings — look for a "re-authorize" or "reconnect" button. If it's there and lit up, that's cause #1.
- Check your sync logs for "rate limit" or "429" errors. That's cause #2.
- Test your webhook endpoint directly — paste the URL in a browser or curl it. If it's unreachable, that's cause #3.
- Is the problem intermittent or constant? Intermittent = usually rate limits. Constant = usually auth or webhook URL.
When to escalate
- You've re-authorized three times and it keeps dropping — that's a deeper OAuth config issue
- The problem is costing you missed bookings or customer no-shows per week
- A vendor quoted you $500+ and you're not sure if it's necessary
- You've spent more than 90 minutes on it without a clear diagnosis
Dealing with this right now?
Scheduling software disconnections are almost always OAuth token expiry or a webhook endpoint that stopped responding after a server restart. Here is the fastest way to confirm which one is your issue.
