Digital Light & Color

Usage scenario :
When making a rotated cropping rectangle, I usually adjust the rotation angle by aligning the edges of the cropping rectangle with some image feature. Doing so may result in slightly setting the cropping rectangle out of image boundary. The usual next step is to click the crop box toolbar button for auto-shrink and shift the rotated crop. I may repeat this sequence for fine tuning the cropping rectangle angle or position.

Issue
The user has to click the auto-shrink after any adjustment ; moreover, if the user does not inspect all edges, a small out-of-boundary condition may go unnoticed.

Would it be possible to keep enabled the "auto shrink and shift", in addition to having it usable on-demand. When "auto shrink and shift" is persistent, the shrink and shift would be executed once after releasing the mouse button.
Having "auto shrink and shift" persistently enabled after any cropping adjustment would (1) make the user interface more efficient and (2) avoid unnoticed out-of-boundary conditions.

I don't think this would work very well. What I recommend instead is using the Level transformation first to rotate and crop the edges. Then use Crop with the normal rectangle.