Warning: Server 2025 upgrade
Automatic Server 2025 upgrade creates licensing risk
Table of contents
What happened?
At every opportunity, IT security experts point out the importance of updates. We too, as an IT systems house, advocate the timely installation of updates at all our IT security talks. Software updates keep your IT systems secure and up to date and are an indispensable component in the fight against the growing cyber threat from the internet. To avoid missing any of these important updates, patch management tools are becoming ever more important. But what happens when a seemingly harmless update suddenly leads to an upgrade? That is exactly what has just happened!
Installing a seemingly harmless update for Windows Server 2019 and 2022 led to an upgrade to the Windows Server 2025 version. This has far-reaching consequences! They range from incompatibilities to server outages due to missing licensing.
What triggered the server upgrade to Windows 2025?
The topic is currently being hotly debated in many forums, and experts agree that Microsoft apparently declared the upgrade as a harmless security update (KB5044284) by mistake. However, it contained code for the upgrade to the 2025 server version. Patch management tools were therefore unable to classify the upgrade correctly and automatically installed it on systems as a supposed security update. Microsoft promptly deactivated the update for servers again. By that time, however, many systems were already affected.
What problems arise from the Server 2025 upgrade?
Our experience has shown that the resulting problems are of various kinds. For some, the unwanted upgrade causes performance and compatibility problems with third-party software; for others, seemingly nothing happens at first.
What unites them all, however, is the problem of missing licences, because the existing licences for Windows 2022 and 2019 are not valid for Windows 2025. Companies where the upgrade was carried out automatically are therefore currently in a kind of “trial version”. This usually lasts 180 days. This means that anyone who does not notice this upgrade will, after this period, unintentionally find themselves in a legal grey area due to the missing licensing, and the server will probably keep shutting itself down after the evaluation period repeatedly.
Challenge for administrators?
The biggest challenge for administrators arises when the upgrade is discovered too late or not at all. Countermeasures are then only possible with difficulty or at very high cost, e.g. by means of a restore, because especially after the 180 days it is difficult to fall back on a suitable backup.
Proactive IT support offers clear advantages here
Consequently, there will be companies that are now running Server 2025 without suitable licences. With reactive IT support, the problem for these companies will only become visible within 180 days at the latest, but then without warning and possibly without the option of restoring a suitable backup. Such an unplanned outage may then drag on for several days.
At our customers, we have already checked all servers and, where necessary, successfully restored the backups. Furthermore, thanks to our proactive IT support, we now have enough time to examine how the servers behave with the 2025 upgrade and whether it might actually make sense for one or other customer to switch to Windows 2025 in the long term – but then with a licence!
