I had encountered this problem on a number of occasions as well, but kept putting off investigating it further. I also thought maybe I had just clicked incorrectly - which would be odd after being a Mac tech for 25 years…but it's possible.
I will give this "feature" more attention & testing because I too use that feature a fair bit - not as extensively as the OP, but as a long-time subscriber, it's one of the features that was making me reconsider my renewal.