Rotated Objects Are Measuring Shorter Or only Measuring Top Shape?

Working on a file provided by a client. I can't find anything wrong in the settings but Illustrator keeps saying the same objects are shorter when rotated veritcally. I've tried ungrouping and copying the items, same result. once ungrouped it only seems to meaures the top object's height. I have never had this come up before. Any suggestions? 

*forum keeps removing the file due to "The attachment's file.ai content type (application/postscript) does not match its file extension and has been removed." - maybe this is part of the problem? It's acting like a normal AI file.