Appreciation post: our billing and CRM stopped syncing for 3 days and nobody noticed because I built a check that emails me

Aaron Grant · 2026-09-24T08:35:03.812264+00:00

Last Tuesday I was on my couch around 9pm and got an alert that 47 invoices were stuck in a sync loop between Stripe and HubSpot. I had set up a simple check 6 months ago that pings me if the counts don't match, and it caught the whole thing before a single customer saw a wrong amount. Ended up spending 90 minutes remapping one field that got renamed in an update, and everything was back to normal by midnight. Honestly felt good to fix something that would have been a mess if it hit on a Friday afternoon. Has anyone else had a silent sync failure bite them, and what did you set up to catch it earlier?

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Appreciation post: our billing and CRM stopped syncing for 3 days and nobody noticed because I built a check that emails me | B2b Saas Ops - Free To Speak