I was on one of our client servers yesterday and after receiving an error due to IE being out of date, looked for an update for it through manually checking Windows Update on our Small Business Server 2011. I noticed only after checking Microsoft Update, I was informed the Windows Update Agent was out of date and that there was a new version (7600.320) -- from August 2014. After about 5 minutes, it returned with a slew of (surprise!) updates that had never been downloaded on the older Agent and were deemed important and recommended.
My question is why hasn't this been brought to my attention prior even by way of a taskbar notification. Yes, we do manually choose what to update but it seems like something like this is critical for receiving updates (especially at the server level). To partially answer my own question, this seems important but also seems optional or not terribly urgent by Microsoft's standards to receive this which left me asking if I should be doing this for all 30+ of our client servers.
I co-manage other servers and only some have the option to manually update the Agent, some still on older versions with no suggested option to update.
This convoluted MS business-as-usual dance reminds me of Inception: update within updates!