A situation occurred where Windows Server 2022 at work was 'automatically upgraded to Windows Server 2025'

A story was posted on Reddit, a bulletin board-style social news site, about a nightmare that occurred when a system administrator came to work as usual and found that the company's Windows Server 2022 system had been upgraded to Windows Server 2025 overnight.

Reddit user Fatboy40, who says he works for a small business in the UK, posted on November 5, 2024, 'Windows 2022 server unexpectedly upgraded to 2025, aaaargh!'

In that thread, Fatboy40 reported, 'This morning I got to work and something was a little odd. Upon further investigation I discovered that our Windows 2022 servers had either been upgraded to 2025 overnight or were about to be upgraded. Needless to say this was a shocker as we are not ready to upgrade for various reasons and do not have the necessary licenses.'

When upgrading the OS of a company's system, IT managers have to be careful because there are many things that need to be paid attention to, such as application and driver compatibility, licenses, support, security settings, etc. Fatboy40 was shocked when the OS was upgraded without his knowledge.

At Fatboy40's workplace, he used products from security company Heimdal to manage updates to client servers.

The Heimdal team immediately began investigating the situation and discovered that the root cause was not a bug in Heimdal's products, but a misclassification of Microsoft updates.

Specifically, the numbering of 'KB5044284,' a Windows 11 update delivered in October 2024, was actually an upgrade to Windows Server 2025. In other words, the 'update' and 'upgrade' of the OS were reversed.

Writing on Reddit, Heimdal manager Andrei Hinodache said, 'It took some time to identify the root cause because our initial footprint was limited, but it turned out that the issue was due to a bug in the Windows Update API. Microsoft had mistakenly labeled the Windows Server 2025 upgrade as 'KB5044284.''

Heimdal estimates that this upgrade issue affects 7% of its customers, and to prevent further issues from occurring, Heimdal immediately blocked KB5044284.

Fatboy40, who was forced to deal with the unexpected upgrade, said, 'Apparently, Microsoft screwed up and it's costing me and my team a few days to recover. I have no confidence that they will take responsibility, but I'm going to see if I can report this to Microsoft through my reseller.'

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