On November 5, Microsoft mistakenly assigned a globally unique identifier (GUID) to the Windows Server 2025 upgrade, leading to confusion among IT professionals. The upgrade was incorrectly labeled as KB5044284, a security update, which caused certain third-party patching software to misclassify it and deploy Windows Server 2025 unexpectedly on some servers. Heimdal, a security firm, reported that a customer found the new operating system installed without prior notice. The licensing check for Server 2025 occurs only after the upgrade is completed, potentially obligating users to purchase a new license without a straightforward rollback option. As of November 7, Microsoft had retracted the problematic update, but no rollback had been made available. Jim Gaynor from IT consultancy Directions on Microsoft emphasized the importance of vigilance in patch management and cautioned against the risks of integrating paid upgrades into security update channels.