Consider the following two sentences.
Sentence 1: I always meet Tom at the mall.
Sentence 2: I'm always meeting Tom at the mall.
The first sentence sounds more like these regular meetings with Tom are planned whereas the latter implies the unplanned nature of such meetings.
This way of interpreting the two sentences seems rather intuitive to me, though I'm not entirely sure why. I have given this some thought, of course. The best explanation I could come up with is that progressive verb forms imply ongoing actions, so that when they're used in the context of Sentence 2, it sounds like the statement is made when the action itself is already ongoing—almost like the speaker only came to realize the action(s) they were performing when they are in the middle of performing the action (hence unplanned)
Does anyone have a better explanation?