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Since using version 11.8 when I print from Drawing Layout Template using Adobe Pro I can not longer print multiple pages and get an error message "Could not start print job" after generating the first page. I've talked with 2020 and they just shrugged their shoulders. I've tried using other pdf printers and I can print multiple pages but if I set to landscape printing only the 1st page prints landscape with additional pages resetting to portrait.
If you do a physical print, does it work OK? If yes then it is the PDF printer you are using. If no then it is 2020 at fault.
I use the free PrimoPDF as a VERY simple and effective Print to PDF function. Our group also uses the free Bullzip PDF but for anything complex, we use PDF Xchange which is completely awesome in every way (but not free).