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basics of CUPS troubleshooting

Having upgraded to Stretch, a file that I need to print no longer prints properly. (It did before.)

I am sure the difficulty is so idiosyncratic no one here will have experienced it. So I'm not asking how to fix it specifically.  Rather I'm looking for advice how to isolate the difficulty, generally speaking.

The file to print is a pdf file and the printer is a Zebra label printer. The file is sent to the printer via command line, lpr. The printer is configured via CUPS web interface. The driver is provided by CUPS (Zebra ZPL label printer) and no external ppd file is required. The file prints without indication of error in the cups error log.

The problem is that the orientation of the file can no longer be changed. (Under Jessie & Wheezy, the orientation would change automatically to accommodate the label dimensions).  Now, even when calling the "orientation-requested" option, the orientation cannot be changed 90 degrees, instead it just flips 180 degrees.

So I'm wondering what changed? Can I somehow isolate the change to a file? Is there documentation what changes might have been made to the file somewhere?

Thanks for reading.

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