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This seems to be a fairly basic expectation and comes in very handy for Designers and Architects who pay a fortune for Acrobat Software and use Acrobat Pro DC to mark up complicated drawings. Yet there doesn't seem to be any way to recognize a shape as an object and rotate/flip/align.
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Hi Dyllon
Hope you are doing well and sorry for the trouble. As described you want to rotate the comment shape, rectangle in PDF.
This functionality is not yet present in Acrobat DC, you may submit your request with the engineering team using the link https://www.adobe.com/products/wishform.html
You may also look at the workaround shared in a similar discussion https://answers.acrobatusers.com/Rotate-Markups-q101520.aspx and see if that helps.
Regards
Amal