After paying a significant bill for many years as a tiny freelance company, I'm finding that I can't even rely on Quickbooks to file 1099's on time, or at all. None of the 10 contractors I've paid this year have received a single document related to 1099. Nor have I been informed of any issues with sending them. You are left completely in the dark as a subscriber to Quickbooks Online. There's no status indication of any contractor paperwork.