Thank you for reporting the issue. We have added the issue to our backlog.
With Best Regards,
An error occurred while saving the commentrlowers commented
As of June 2019, this shadow rotation issue has not been fixed in Illustrator CC. I also work in packaging and need to rotate logos for various side panels. In the past, you created a symbol of the logo plus shadow and it rotated perfectly 180 or 90 degrees. Today I had to flip a logo 180 degrees and manually correct the shadow.