I pay Upwork for work done by subcontractors. How do I classify those expenses since I am not paying the subs directly? Upwork's site says I don't need to send 1099s.

You can categorize this payment as Payment to contractors, even if you did not pay directly your sub-contractors. In fact, Upwork is your sub-contractor.

Hi,

I'm having the same question. I was categorizing them as "Contract Labor". I don't see a category called "Payment to contractors".

Do all the services I categorize as "Contract Labor" require that I generate1099s?

For example, I also have a virtual assistant that she charges me monthly via her company. Do I categorize her as "Contract Labor" or "Legal and Professional Services"?

If there is a specific category it fits into, e.g.  "Legal and Professional Services", use that. Otherwise use contract labor.  Another option is use "other expenses" where you can more specifically describe what you paid for in part V of Schedule C.