Me: "No, you have to press the button with your left pinky."
Coworker: "What? Why would that matter."
I've always wanted to do something like that, fortunately it was a lot funnier than me retelling it here. It always is...
Now before you get too nasty, I did help him. He was actually doing everything right. The problem: he set the scaling to fit in 1 page high by 1 page wide. This negates any page breaks you've set. In this case he changed the setting to 2 pages wide and then adjusted where the page break fell in page break preview mode.
Most of the time I find my sheets are longer than they are wide. When I don't know how many pages my printed file will be I will set it to 1 page wide, but delete the pages high entry. This will automatically set the printout to fit one page wide and however many sheets it needs to print.