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TL;DR: install MS patch requires previous patches, how to determine needed patches in an isolated network?

I have this Windows 2008R2 SP1 machine in a isolated network, the machine hasn't been patched since 2015, which means a lot of patches are missing.

Directly installing latest patche proved to be unfeasible, the WUSA will check and then report 'Patch Not Applicable', however as to my knowledge, 'Patch Not Applicable' has only 3 reasons:

  • system architecture mismatch (not the case, easily checked)

  • newer patch which integrated previous patch was installed. (not the case, not patched since 2015)

  • patch pre-requisite not satisfied.

How do I determine the exact pre-requisite patches (a chain of patches)? (preferably from querying WSUS server programmatically? )

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That sounds super annoying. Setup a WSUS box, connect it to the internet and update it, then bring it to the isolated network and query against that? That's what I would do. Anything else would be so time consuming it's not worth the trouble. Plus you wouldn't really know if you missed something.

  • problem is, when you query the WSUS server, it would only return the currently needed patch for querying machine, no patch route to target patch is explicitly given. – Sajuuk Apr 29 at 5:13
  • I was more so referring to this scenario as a means to run all the updates on a specific OS without actually have internet. WSUS would allow you to download the updates giving the machine/VM running WSUS internet connectivity and then pre-downloading the updates. Once you query the WSUS server then your 'offline' server could be brought up to date using that data. You would not need to do it onesy-twosy. That seems like a waste of time to me. – thelanranger May 2 at 21:32
  • that's neat, however the core of this problem lies in determining the minimum viable patch path. not how to upgrade a machine to its newest state. – Sajuuk May 5 at 1:56
  • Ah, so you're just trying to find the 1 or 2 patches you can install to get an application to run, not get the system patched up to current? That could prove an insanely complex task. Your application could have libraries that need to be installed, those libraries could have prerequisites, those prerequisites could have prerequisites, etc. Generally why apps use installers to deploy or give you their prerequisite list of "Server 2008 R2 SP1 + .NET 4.0" or something. – thelanranger May 5 at 21:10
  • well I'm talking about security patch here, so that I could install one security patch to defend against some vulnerability without install all the other unnecessary patches. – Sajuuk May 6 at 1:52

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