When you go to File > Print, are you sure you have the paper size, type, and orientation exactly matching the bypass tray and have it exactly match what the device says is loaded?
I am trying to print an envelope from Word 10 and am doing everything as it says... inserting the envelope as seen on the screen, and yet the envelope comes out with the address printing in the wrong direction (vertical). No, I do not have the clockwise rotation on. I can't seem to get this to work! What is going on? Before the software upgrade I had no problems printing envelopes.