Square and Cash App experienced a system-wide outage on February 26 caused by a faulty security certificate bundle deployment.
•A routine certificate bundle update at 19:40 UTC broke communication between payment systems and databases, with errors detected by 20:00 UTC
•Payment systems were impacted by 20:20 UTC; the problematic certificate was rolled back at 20:42 UTC, about an hour after deployment
•Offline payment mode was automatically activated at 20:53 UTC to stabilize card-present transactions during recovery
•Core functionality was restored by 21:03 UTC, with full resolution at 22:13 UTC; reporting services remained impacted for roughly an additional hour
•Planned improvements include eliminating manual certificate update processes, auditing all deployment surfaces, and improving offline payment reliability during incidents
