Wow, this is more troublesome than expected.
Goal: Let users upload images straight from a camera and manually select an area of the image that should be cropped.
Issue: nearly all modern cameras use EXIF information to tell an images orientation. Drupal image actions ignore this information and all images in landscape format resulting in flipped portrait images. Imagecache Actions module provides an action to rotate images based on EXIF data. But: this doesn't work if the image was resized to the maximum dimensions straight after the upload. And: it doesn't play nice with most image cropping modules.
I've been fighting this issue for some hours now and have something that seems to work for me. It's not extensively tested yet, though. Here's what I came up with: