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Upgrading Windows 10 via WSUS

Windows 10 is supposedly the “last” consumer Windows edition Microsoft will release. While the version will stay as 10, over time the whole OS will mature, grow and mutate into something that will look and feel very different from the original release of July 2015. One side effect of this is that in a corporate environment using WSUS, it becomes possible for new versions of Windows 10 to be deployed as an in place fully automatic upgrade, the same way any other patch or service pack is installed. I was curious to see how this worked, so I approved the Anniversary Update (also known as version 1607) for installation at work and let my PC download the update.

Sure enough, the process was the same as what my home PC went through when it upgraded to the 1607 update. A couple of update screens and quite some time later, I was back at my desktop, duly upgraded. Everything was still in place, bar the RSAT pack which had to be updated to a version compatible with v1607. Overall, an extremely smooth and hands free process, just time consuming. I imagine it would easily take twice or thrice as long if the machine runs on a mechanical HD and not a SSD.

That being said, there was one major problem with the 1607 update – checking for updates from WSUS broke due to a bug in 1607. Windows 10 1607 would start to search for updates from the configured WSUS server, only to have multiple services in the background crash repeatedly, with no indication to the user. To the end user, it simply looks like the search is stuck at 1% and never moves from there. Apparently, if one leaves the process running long enough, updates will eventually download. This is obviously an unacceptable bug and Microsoft were made aware of it. They promised a fix in one of the monthly update roll ups, which was subsequently delivered and verified as having fixed the problem. Now you have a chicken and egg situation: deploy the 1607 update via WSUS, but then struggle after that, since you need the Cumulative Update to fix the problem.

You could manually install the update, but this becomes unwieldy in a large organisation. If deploying Windows 10 via deployment tools, you could make sure that the base image has the update injected already, which prevents the issue from cropping up in the first place. Sadly, the 1607 update is delivered from WSUS as an encrypted ESD file. While it is possible to decrypt this and inject the update, I don’t know if it’s possible to convert that back in to an ESD file. Even if you could, the checksum wouldn’t be valid and WSUS would probably fail to work with the modified file.

There’s always a possibility Microsoft could revise the 1607 update in WSUS so that the ESD file comes with the last Cumulative Update installed so that it works correctly out the box. I recall something like this happening with the November 1511 update, which I declined as it was another 3-4 GB download. Unfortunately, one doesn’t know when or even if this will happen. It’s also possible the problem will never be fixed. With the Creators Update due out early 2017 (March?) it’s possible that Microsoft uses that as the new baseline. If I’m correct, once the Creators Update is approved in the WSUS console, it will supersede the Anniversary Update, so the problem should be solved by bypassing the 1607 update.

I look forward to eventually rolling out Windows versions like this, though I think it will be beneficial if every computer had a SSD inside it first. Mechanical hard drives really do slow things down these days. A nice side effect of this is that Windows shouldn’t end up suffering from “Windows rot” as the Windows directory is replaced with each major upgrade. This should keep performance up compared to something like Windows 7 that gets bogged down after years worth of updates. Interesting times ahead…

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