Image Export "to selected boundary" - But not really?

Am I missing something? When I have an image loaded & export the image cropped to *any* boundary (I use amoebas, grids, etc.), the resultant image is rectangular when viewed in anything other than GM. I don't recall always having this issue.

A majority of my work in this regard is receiving anywhere from 5-100 miles of georeferenced corridor imagery. I then break it into more manageable image chunks (1 mile to 5 miles for instance) along the corridor. Resultant images are then loaded into Civil3d. I can't get those images to NOT be an absolute mess. If I bound the export to an aligned grid along the corridor, it makes a ridiculous overlap mess. Option B is cardinal aligned grid to export to, but then I end up with 3x the images necessary to cover the corridor.

Am I missing some crucial part of the workflow somehow? Also ~ side note...I can't get Civil3d to load any GM exported imagery with transparent background. Attempting to re-assign transparent pixels in C3D crashes the software.
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