I am having the same issue. I have 23 contractors to send 1099's to but 11 show up when I attempt to process the 1099's. I viewed and tried several suggestions from the forum and tried to actually contact a human from Intuit by online with no luck.

-All of the contractors track 1099's boxes are checked

-All have been paid by check and meet the threshold

-The account used to pay them is selected in the dropdown for box 7: Non-employee compensation

-They appear and are checked in green on the vendor list when I select to add them

-None of the "HELP" links address anything other than the obvious above

-My account can't even figure it out and she has a degree in accounting