Windows AMIs With Even Fewer Tears

Some recent image building work I was doing required images based on Windows Server. One of my more popular posts, Windows AMIs Without the Tears, detailed the fraught endeavor of making the WinRM management system work for this purpose, but since then Microsoft have substantially improved the situation by committing engineering effort to porting OpenSSH to Windows.

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Windows AMIs Without The Tears

Twice in the last couple of weeks I've helped automate build infrastructure in AWS, first for Event Store and then secondly for another company. Both times we got 90% of the way there using great tools like Terraform and Packer, and fell at the last hurdle: how do you build Windows images in an automated fashion (i.e. no point-and-click)?

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