Hello Caleb Pourchot,
Thank you for posting your question in the Microsoft Q&A forum.
The issue you're encountering stems from Azure DevOps' transition away from Windows Server 2019, even when specifying "windows-latest" as the VM image. While "windows-latest" should theoretically use the newest available image, Microsoft's brownout period is causing unexpected failures as they phase out older versions. Your pipeline correctly defines the image variable, but the underlying infrastructure is enforcing compatibility checks during this transitional period.
The error message explicitly indicates this is part of Microsoft's planned deprecation process for Windows 2019 runners.
To resolve this, you could either wait for Microsoft to complete their migration (as "windows-latest" will eventually point to newer versions automatically) or explicitly specify "windows-2022" in your YAML to bypass the brownout restrictions. This situation highlights how cloud platform updates can sometimes impact pipelines unexpectedly, even when using version-agnostic labels like "latest."
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