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Windows Server 2025 Update Debacle

Jan 9, 2025 | News

In November 2024, Microsoft experienced a significant mishap that inadvertently labelled a full-scale Windows Server 2025 operating system upgrade as a routine security patch. This error had some significant consequences…

A 5GB “Security Patch”

At the core of the issue was the mislabelling of the Windows Server 2025 upgrade, a 5-gigabyte package, as a security update. Many automated patch management systems are programmed to deploy security patches automatically and soon after release. So when this release dropped they overnight installed this massive update without a second thought. The result was many systems prematurely upgraded to Windows 2025 with implications for applications and licensing budgets alike!

Impact

The patch release caused a lot of chaos, the first big impact was the down time. Upgrading to Windows 2025 took a long time and even if the upgrade of the OS worked well, it took hours to complete.

Next, some applications simply did not work on the new operating system. Rolling back was not possible so service interruption was inevitable in these cases.

Plus, one area where people have inadvertently got stung is that despite this glitch being a Microsoft mistake, they are now required to have Server 2025 licensing in place. This cost some businesses thousands to true up!

moving forward

This event underscores the importance of designing resilient systems and processes.

  • Audit Your Automation: Regularly review and update your automated patch management configurations to ensure they are aligned with best practices.
  • Train Your Team: Equip your IT team with the skills to identify potential red flags in update processes, even in highly automated environments.
  • Be Prepared: Mistakes happen even from big players like microsoft. Have a plan of action for when something bad happens, and better, have the plan rehearsed so you know what to do and that the plan works
  • Use VMhosts Platform: Ok, this is a bit cheeky but why not use a UK based cloud platform where Windows licensing is included, DR roll back to the second of issue is possible and long term backups are part of the offering!

 

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