Thanks everyone for the additional info! It definitely sounds like Health Check is linked. I've never set up, or used Health Check, so it is one of those features that wasn't suspicious to me originally. One feature that I thought might be related was that CCleaner, at some point, added CCleaner cookies to the excluded list of cookies by default, but when I removed that entry from the list this problem continued.
This has been a recent bug. I'm not sure what version in which it began because it has persisted through several versions. It occurs on all sections in both the 'Windows' tab as well as the 'Applications' tab. The weirdest part is that the bug does not always occur. I can exit, reopen, and it persists, or I can exit, reopen, and it doesn't persist - it is very random. I have attached a sample screenshot.