A trucking vendor has sold their invoices to a factoring company, which we are to pay directly. To whom do we issue the 1099, the vendor or the factoring company we actually paid?

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The 1099 goes to your vendor, not the factor. The vendor is still the beneficial owner of the income.  You might want to set up the factor as the “remit to” in the vendor’s record. The factor is not your vendor, but a vendor of your vendor!

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