Microsoft Confirms September Windows Updates Can Break Always On VPN, Because Of Course They Fucking Can

Right, so Microsoft has finally admitted that some September Windows updates can break Always On VPN on affected devices. You know, that tiny, insignificant feature people rely on to actually connect to corporate networks and do their goddamn jobs. Apparently, after installing certain September 2024 security updates, Windows clients may fail to establish Always On VPN connections. Splendid work. Truly enterprise-grade chaos.

The issue affects devices running Windows 11, Windows 10, and some Windows Server configurations acting as VPN clients. Microsoft says the problem shows up particularly with Always On VPN connections using certificate-based authentication. So if your environment was set up the way it was bloody supposed to be, congratulations, you may have won yourself a support nightmare.

Symptoms include failed VPN connections and users being unable to connect automatically, which rather defeats the whole damned point of something called Always On VPN. If users have to manually poke, prod, and sacrifice a goat to get connected, then it’s not “always on,” is it? It’s “occasionally sulking in the corner VPN.”

Microsoft has acknowledged the issue and says it is working on a resolution. In the meantime, admins are left doing what admins always do when vendors cock things up: reading advisories, calming angry users, checking update histories, and wondering whether patching systems for security this month was really worth detonating remote access for half the company. Fantastic.

The article points out that this is a known issue tied to the September updates, and Microsoft has documented it in the Windows release health dashboard. In other words, yes, it’s real, no, you’re not imagining it, and yes, the update may have kneecapped your VPN because apparently regression testing was too much fucking effort.

The practical takeaway is painfully simple: if your Always On VPN suddenly stopped working after September updates, the updates are a prime suspect. Admins should verify affected systems, keep an eye on Microsoft’s guidance, and prepare for the usual parade of temporary workarounds, delayed fixes, and user complaints written as if you personally coded the bug during your lunch break.

So the summary is this: Microsoft shipped updates, Always On VPN got kicked in the teeth, remote users got shafted, and admins got handed another bucket of shit with a KB number attached to it. Business as usual in the enchanted kingdom of Windows servicing.

Anecdote time: years ago, a manager asked me why remote staff couldn’t connect after Patch Tuesday. I told him the update had “introduced a networking inconsistency.” What I meant was Microsoft had fucked the VPN again. He asked how long the fix would take. I said, “That depends. How fast can Redmond stop setting fire to the plumbing?” He didn’t laugh. I did.

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Source: https://4sysops.com/archives/microsoft-confirms-september-windows-updates-can-break-always-on-vpn/