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I have a need/desire to obtain multiple windows VMs patched up to specific dates to use for testing malware and exploits - e.g. to allow automatic evaluation like "X behaves one way until November 2015, and differently afterwards".

Is there a reasonable way to make such VMs without too much manual labor? I.e. start with a "fresh" VM and configure it (preferably in a way that can be automated by a script) to install only security updates up until date xxx / version yyy, but not anything later?

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Just like WSUS, SCCM (or a similar product) would be an option to download patches en mass and assign them into deployment groups or packages for deployment. With a bit of scripting (or not), it could be very flexible for a variety of OS and build combinations.

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only by using WSUS and per-machine rules it is possible, but I hardly beleive that you will be able to perform a clear simulation, i.e. install updates that are in cumulative ones now

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    This is really a comment and not an answer to the original question. You can always comment on your own posts, and once you have sufficient reputation you will be able to comment on any post. Please read Why do I need 50 reputation to comment? What can I do instead?
    – DavidPostill
    Feb 11, 2017 at 11:45
  • This answer looks like comment, I totally agree. But I don't see any way to expand it because it is that simple. If there's some additional details you think that can be added - you're welcome to ask, I'll expand my answer gladly! My goal is to help people, and more comprehensive answers are better in helping others. Feb 11, 2017 at 21:26

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