I was having the same issue for quite some time. I reached out to customer service and they couldn't figure it out. 

After trying a couple of the suggestions here, I finally got this figured out. When you add an expense, you have to make sure that your category type (material, labor, insurance, etc) is actually categorized as "expense" and not "bank." This may or may not help, but it's worth a shot. Worked for me. Good luck!