Microsoft Breaks VPNs, Then Heroically Fixes the Shit They Broke

Right, here we fucking go. Microsoft shoved out September 2024 Windows updates, and—surprise, surprise—managed to kneecap VPN connections on Windows devices. Because apparently testing updates before lobbing them into production is still considered some kind of optional luxury in Redmond.

The bug hit VPN connections after users installed the September security updates. Microsoft eventually admitted there was a problem, which is corporate speak for “yes, we broke it, now stop yelling.” The issue affected multiple Windows versions, and people started seeing their VPNs fail after installing the patches. You know, the very patches you’re supposed to install to stay secure. Lovely bit of fucking symmetry there.

To clean up the mess, Microsoft rolled out a fix through its Known Issue Rollback system for managed enterprise devices and pushed out a broader resolution so affected users could get their VPN functionality back. In other words: they applied a bandage after stabbing the patient and then expected applause for the medical intervention.

The company says the fix should propagate automatically to consumer and unmanaged business devices, though some systems may need a restart to fully receive the rollback. Because of course they do. It wouldn’t be Windows if solving one problem didn’t involve “have you tried rebooting the bloody thing?” as the sacred incantation.

For enterprise admins, Microsoft also provided Group Policy-based mitigation details, because when one of their updates detonates in the server room, it’s naturally your job to sweep up the shards, explain it to management, and pretend this is all part of a healthy patching ecosystem rather than the same clown parade with different KB numbers.

So the short version is this: Microsoft’s September updates borked VPNs, users got hosed, admins got stuck firefighting, and Microsoft has now issued a fix to undo the damage. A textbook case of “we’re committed to quality” delivered with all the grace of a drunk badger crashing through a printer.

Anecdote time: this reminds me of a place where a vendor patch once took out remote access for half the company on a Friday afternoon. Management asked how long until it was fixed, and I told them, “Roughly the time it takes for the vendor to admit they cocked it up and for me to stop laughing.” They didn’t appreciate the honesty. Philistines.

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https://www.bleepingcomputer.com/news/microsoft/microsoft-fixes-vpn-issues-caused-by-september-windows-updates/