Do landlords need to issue 1099s to contractors?
Generally yes, past a certain threshold — and it's a common blind spot because most landlords aren't tracking it as the year goes.
Every landlord who's had a handyman fix something, hired a landscaper, or paid a contractor for a repair has probably crossed this threshold without thinking about it. It's not a complicated rule — it's just an easy one to lose track of when payments happen throughout the year instead of all at once.
The general rule
If you paid an unincorporated contractor or service provider $600 or more total during the year for work on your rental property, you generally need to issue them a Form 1099-NEC. Payments to most corporations are typically exempt, though there are exceptions. This is general guidance, not tax advice specific to your situation — confirm the details with your CPA.
Why it becomes a scramble
Nobody tracks this in the moment — a handyman gets paid $200 in March, another $250 in July, and by December you've crossed $600 without anyone noticing until your CPA asks who you paid this year. The practical fix is simple but easy to skip: collect a W-9 before the first payment, and track contractor payments as they happen instead of reconstructing them from bank statements in January.
Nobody notices they crossed $600. That's exactly why it needs tracking, not memory.
This is part of what proper monthly bookkeeping catches automatically — see real estate investor bookkeeping, or if a contractor works on your own business rather than your rental, contractor bookkeeping covers the other side of this.
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