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Unexpected Auto Upgrades: Windows Server 2022 Jumps to 2025

November 7, 2024

By Peter Barnett

(Note: This post was edited for accuracy and to reflect more information that came to light as this situation evolved.)
In the world of IT management, unexpected updates can disrupt operational stability and lead to licensing and compliance issues. Recently, an anomaly with Windows Server updates caused considerable disruption as Windows Server 2022 systems were inadvertently upgraded to Windows Server 2025 due to a change in how in-place upgrades will be handled in the future of Microsoft server OS products. This change was not properly communicated to technical vendors or customers, so it caught both somewhat off-guard. This incident highlights the importance of rigorous patch management practices and administrator control over update approvals, as well as rigorous testing, to prevent the application of unexpected or even defective patches.

Action1’s Commitment to Controlled Update Management

At Action1, we understand the potential risks of automatic updates and the need for administrators to have full control over the update process. The Action1 platform allows administrators to review, test, and selectively approve each update. This flexibility ensures that regardless of how an update is classified, updates do not proceed to critical infrastructure until administrators have confirmed they meet organizational standards for stability and compatibility. This includes unexpected updates, like KB5044284, in which a server OS upgrade came down as a security update. Administrators can choose to withhold deployment until testing is complete.

Preventive Measures and Manual Update Trials

Upon hearing reports of the anomalous behavior in the update, our expert team at Action1 promptly manually tested the installation of KB5044284 update on Windows Server 2022. The results of our testing were clear; the update delivered through the window update channel did not execute correctly, and in our testing, failed to convert the system to Windows Server 2025. This test was an essential part of our strategy to ensure the integrity and stability of our user environments.

Empowering Administrators with Update Autonomy

Action1 empowers administrators by providing tools to thoroughly review, test, and make informed decisions about each update. This control is essential in maintaining operational consistency, compliance, and stability, especially when faced with anomalies. Administrators can customize update deployment settings, ensuring updates only roll out after thorough vetting. This level of control is vital in preventing unwanted upgrades and maintaining operational consistency and licensing compliance.

About Action1

Action1 reinvents patching with an infinitely scalable, highly secure, cloud-native platform configurable in 5 minutes — it just works and is always free for the first 100 endpoints, with no functional limits. Featuring unified OS and third-party patching with peer-to-peer patch distribution and real-time vulnerability assessments with no VPN needed, it enables autonomous endpoint management that preempts ransomware and security risks, all while eliminating costly routine labor. Trusted by thousands of enterprises managing millions of endpoints globally, Action1 is certified for SOC 2 and ISO 27001.
The company is founder-led by industry veterans Alex Vovk and Mike Walters, who founded Netwrix, which has grown into a multi-billion-dollar industry-leading cybersecurity company.

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