Ever since Creative Cloud 2020 (definitely the past few updates), I run into the following error:
1) Crop Tool; 2) Rotate the image with transparent parts being introduced; 3) Have Content-Aware checked (it's specifically there for this very reason, to fill in the now transparent parts); 4) Select any Tool; 5) Error
When I click the checkmark in the Crop Tool settings first, it works and processes just fine, but selecting any tool used to work just as well (if not better, given the advantage of already having the next tool at your disposal). Apparently it now absolutely requires to click the checkmark first, for it otherwise will throw the error without exception.
If one forgets to press the checkmark, they either need to start all over, or would need to click away the error, manually select the transparent parts and use Content-Aware separately. Both these scenarios add at the very least 5 extra steps to the process.
And given how overly technical and not user-friendly the error message is, I highly doubt it is supposed to be like this.