
and

I was unable to locate any event log entries related to this issue and I didn't see anything out of the ordinary in setuperr.log. Further, automatic updates was reporting that two IE7 hotfixes needed to be downloaded and installed. When I did that the two dialog boxes above no longer appeared at logon.
Through a lot of testing and some basic process of elimination it seems that one of two things is happening. Either the recompress plugin is doing something wrong with NR's IE7 addon or there is something about that addon which needs to be coded differently in order for the recompress plugin to work with it.
What I ended up doing was completely forgoing the recompression of not only all addons, but the update pack as well. I wish I could give some more concrete answers and solutions here, but after dedicating two days to this, I really need to catch up on the ever growing list tasks I have to do at work.
Some further information I can provide is that I have been using the cache driver.cab and optimize files features in all scenarios, so I don't think there's an issue with those.