Exporting a Layered PSD and Overprint Fill

Hi guys.
I'm trying to export a layered PSD of my AI file and I keep having problems with it merging the layers because of the overprint settings.
I've been trying to go through and turn off the overprint in my objects, but I have a photo that's cropped by a rectangle shape, and the Overprint Fill option under Attributes is greyed out. What must I do?

Well, when I release the clipping mask, both the image and the selection mask do not have the overprint checked or greyed. But when I apply the mask, it turns grey again (with a "-").
The clipping mask:
The Image:
Masked:

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