Can't swivel an image

When I go to swivel an image more than ~40-50 degrees in PP, it turns the whole graphic black, in both the preview pane and when I export it.
Please tell me I'm doing something wrong, and that it isn't an issue with PP. It will make a project I'm doing so much harder if I can't swivel images as I'll have to turn each one into a one-frame video clip and then re-import it and apply the effects that way. Tedious, especially when you've got several dozen (or more) images.
FWIW/FYI I can swivel video clips and text just fine, but any image file (PSD, PNG, JPG) glitches and turns into a black rectangle when it rotates more than a certain number of degrees. The glitch occurs on both a newer Mac and newer PC, and in both CS6 and CC.

I did some more testing, and it seems I am able to get some PNG files (with transparency) to swivel correctly, but not others. I also figured out that my 300 x 300 pixel red dot that wasn't working works just fine if I resize it up to 3000 x 3000. Weird.
In case you want to test, below are two files: the first swivels correctly, while the second turns black about halfway into the 90 degree swivel. The only difference between the two images is that I cropped the sides of the second. I have no idea why this is.

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