Possible bug, ver 0.12.3.1
On day 52, the scene for punishing Debbie, I had her remove clothing including skirt, Miss Newman search her, then I photographed her in front of the whiteboad, then had her bend over the desk to be spanked and paddled. Then I had her lay over Miss Newman's lap and select the "massage" action.
At this point, her pain is 4 of 4, humiliation is 3 of 4 and pleasure 0 of 4.
I then selected the "massage" action. The game then said "This time around I need to make sure Debbie is in pain and humiliated before beginning to provide her with pleasure. As a minimum she should be stripped of her skirt, paddled and body searched before I take this action."
I did all of the above. Though if humiliation needs to be 4 of 4, I see no way to achieve that.
I did back up to ordering her over Miss Newman's lap, then had her spanked (second spanking as she had already been spanked over the desk), then massage, but same messages.