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Not being able to find "crop" in the Help section drove me nuts. Here's my take on how to do this (step-by-step):

- How to CROP an image to a canvas or object
- Select the canvas or object
- Open Inspector
- Style
- Image
- The big rectangle at the top left is called the "Image Well"
- DRAG your image from your desktop or a Finder window right ONTO
the Image Well
- If you have problems doing this:
- Position both OmniGraffle and the Finder window on your
desktop so BOTH are completely visible, including
OmniGraffle's inspector
- Make SURE the graphic file is visible in Finder
- Make SURE the "focus" is on OmniGraffle and the Inspector
window
- Now click and drag the image file from the Finder window
right onto the Image Well
- DON'T WORRY that you are not first "selecting" the image in
the Finder window, or that it isn't "pre-highlighted"
(selected); this will work anyway
- Do NOT drag the image right onto the canvas or object
- That will only PREVENT you from cropping later on
- Now you can use the slider control directly below the Image Well
to shrink/enlarge the image until it correctly bleeds right to
the edge(s) of (fills) the canvas or object; and FYI whichever edges
(L/R or T/B) are going to get "cropped out" you won't have the benefit of
seeing; you'll only be able to monitor the "final outcrop" of your (this)
cropping operation