I'm sure he did give it a good try, yes. There were communications back and forth where he initially found it difficult, said he had some things to try, then said those things didn't work and that he was worried about scratching the case back trying any more. I said that the watch already had a scratch on the case back (my fault) and that I'd like him to try further, but exercise his judgment if he thought it was impossible, and to stop if he felt he was going to do damage.
I will say that while I wouldn't have minded more frequent communication, I feel that he's been honest and straightforward with me the whole time, so I can't really complain about him. I'm just disappointed about how it worked out.