After numerous tests to make this work, I've finally come here to ask for help. A vendor that we use for some of our printing is now requiring us to send them PDFs for all 2 sided jobs that, no matter what the orientation, will print head-to-head. Previous to this change, I would create all PDFs with customized Press Quality job options to retain the highest resolution possible. But when using 'press quality' job options, any landscape jobs would automatically rotate to portrait. What this means to us now is that, for example, a 2 sided, landscape business card would result in a portrait PDF that when sent to this particular vendor would end up having the second side printed upside down. I've spent hours tweaking job options for Acrobat clicking and unclicking anything I thought might give me a correct PDF and just when I think I have it right and am producing a press quality landscape PDF, their system rotates the artwork and gets bounced. I've contacted them about this issue and they are laying the responsibility solely on my shoulders and I am out of ways to make this work. They've told me to open my PDFs in illustrator and that is supposed to show me whether a PDF is truly landscape or portrait but no matter what orientation PDF I end up with, in illustrator it opens as a portrait page. I've sent them several test files, which they returned with a lengthy multiple step process of how they managed to get my files to work, (open in acrobat, save as PS files, open in distiller to create new PDFs.) I've tried this on my files and still have not had success. I've tried this from two different applications (CorelDraw and InDesign CS4) with the exact same result. I've tried printing to PS files first and distilling to PDFs. Same result. I've tried printing to PS files through my rip and then distilling to PDFs. Same result. What can I possibly be missing? Source.