Windows 7, KB4474419 & failed update - Tutorial

Updated: November 27, 2019

The end of support for Windows 7 might be just around the corner. That does not prevent me from having my first ever failed Windows Update on this spectacular operating system - not sure if this is a sign of things to come. Indeed, I have an old laptop that I've not used in about a year, and I decided to run Windows Update on it. The first thing it needed were the new cryptographic signature patches, to be able to install future rollups.

I got the prompt for KB4474419 via Windows Update, ran it, seemingly all way fine. But then, at about 70% mark, I saw a message that said: Failure configuring updates, reverting changes. Something along those lines. Never before have I seen this happen, so I set about troubleshooting and fixing the issue. Follow me.

Problem in more detail

As Microsoft says, since roughly mid-2019, you need two patches to be able to install new Windows Updates. These two are KB4474419, which was updated a few times this year, and KB4490628. Both are available either through Windows Update or the Catalog online.

I had no issue configuring the latter, but the first one just kept failing. I tried multiple methods to get it installed, and it simply wouldn't, no matter what. To save you two days worth of trial & error, let me walk you quickly through what I did, so you won't have to.

Installing update

Installation Failure: Windows failed to install the following update with error 0x80004005: 2019-03 Security Update for Windows 7 for x64-based Systems (KB4474419).

Troubleshooter, errors fixed

Solution

I decided to read a little more on the update itself, and then something stood out - the second or third iteration of this update had a boot manager fix included, which seems kind of weird. And then, I thought, this laptop is actually a dual-boot system, running in this case Manjaro Illyria Plasma. Maybe the update failure stems from the bootloader update. Windows wants and expects its own bootloader to be there, but it's actually GRUB that does it, and so the update fails.

To verify this hypothesis, I un-did my dual-boot setup. I restored Windows MBR with the mbr tool, and then changed the partition boot flag using Gparted in a Linux live session. After reboot, I only had Windows available, and ran the update again. This time, it was successful. The end result is, my testing shows, if you have dual-boot, you might face problems with the later revisions of KB4474419. The original March version one didn't touch the MBR and works fine. In fact, you're good all the way up to July or August with this update.

Updates done

Conclusion

What I wrote in this article will probably not be applicable to everyone, but it definitely makes sense, when you think about it. However, never before have I had any issues with Windows assuming its primacy when it comes to the bootloader, and it's sad to see this transpire 10 years into the Windows 7 life, and so close to the end of support date. With Windows 10 updates not having such a stellar quality record overall, open quotation marks understatement close quotation marks, and now this, I'm not so sure what lies ahead when it comes to update reliability.

The error message is also not very helpful, and the whole thing feels rushed. I mean, the update had four revisions in about six months, and that's a bit ... hectic. I hope you will find this little tutorial useful, if anything as a gentle warning that you should be careful with updates, keep a system image, and if push comes to shove, not cave into pressure. A stable, functioning system always trumps the security drama card. So there we are, and if this tribulation helps you a little or something, then feel free to buy me a virtual beer in some virtual pub somewhere.

Cheers.

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