Dave Davison wrote:I got a prompt last night that there were five updates available so clicked the accept tab and retired for the night. Just now I looked at my update History and see the one that persistently fails.
Not everything can be a "one-liner" post. In for example the Office sub forums we see loungers work on files or code, uploading and downloading every day, sometimes there is quite a bit of work put into those files, but the posts are often short. If I think it is needed, or to put something in context, I'll post it.
Background, general comments
You mention 5 updates, and that's fine, but I'm afraid we can all see a different number of updates for the OS and other software.
(At the moment I also see 5 updates on one Windows 7 machine: the monthly rollup; the September update to the SHA-2 code support; and three Office updates, but there is no sign of the updated servicing stack for September, KB4516655, it should be there since it was empty (no pending updates) before Patch Tuesday (10/9). This is a problem discussed at different places on the net, but I won't dwell on that in your thread unless someone else has comments about it.)
I'll try to put it as short as I can: if you are going to install September patches (some prefer to wait a couple of days), this would be the safe way:
First: KB4474419 (that's the latest SHA-2 code support, it's "good" to have when installing the other updates, read: requirement),
Second: KB4516655 (the Servicing Stack update, if offered),
And finally: September's monthly rollup, KB4516065.
If you have tried to install updates and find a failed update, I would bet it's because you are missing the SHA-2 code update, since the updates are signed using SHA-2, but could also be because of missing the Servicing Stack update (that has at least happened earlier).
Now, looking at your attached image; that is in some cases some quite old updates dropping down the tube.

I'll concentrate on the 16/9, but I notice that you successfully installed the Servicing Stack Update, KB4516655, yesterday 15/9.
It starts with the failed monthly update, KB4516065. The first successful today was KB2984976 from 2014, gosh.
(Just a small comment, no need to know/understand;

it's an update about Remote Desktop Protocol (RDP), I think there have been some recent vulnerabilities related to RDP, and it is possible that recent updates need this one to be installed, so if missed earlier it will pop-up, but I have not looked closer at it.)
After that follows three other old updates that also failed to install, KB3020388, KB2923545, and KB3075226, two important and one recommended, all three from 2014 and 2015 and related to Remote Desktop Protocol as the successful one mentioned above. That's 5 altogether.
Question
I cannot tell from your screenshots (both of them) if you have the latest version of KB4474419 SHA-2 code support (some call it v3). It would explain the failed monthly rollup, but not the other three (since, if I understand things correct, they would not rely on SHA-2, but what do I know).
To start with the most recent of the failed updates, the monthly rollup KB4516065, you will need to install the latest version of KB4474419 if it is not already installed. Either it is offered in your Windows Update or you will have to download it manually, install it and let the PC reboot. I could point you to the KB article
KB4474419, but the download link will point you to MSFT
Update Catalog for KB4474419, and there you will find plenty of different versions of the same update. It is easy to pick if one knows what to look for, but I appreciate that it can be a problem. I gather you are running Windows 7 64-bit, is that right?
Byelingual When you speak two languages but start losing vocabulary in both of them.