HI @dylan_stoddard,
I installed Sierra on my Macbook Pro and then ran a SaveAs PDF in AutoCAD 2014 and 2016 and was able to duplicate what you are seeing with your image files printing as black boxes.
Currently Sierra is not a supported platform so I don't have any workarounds but will work to see if I can find something that will make this work for you.
Thanks for your patience on this issue.
John Vellek
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