Can I send multiple 1099s to vendors with different DBA names, but having the same owner company? Each DBA company has a different amount.

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No, you should not issue separate 1099s to each DBA; you should issue one 1099 to the owner. The IRS will match the tax ID number (TIN) to the legal name, not to a DBA; though you can issue checks to DBAs, reporting must be to the legal name of the organization and its matching TIN.

IRS Information Agent Ms. Tennett (ID#1001307512) says that you should aggregate all payments made to a single legal name/tax ID on a single 1099 with the legal name on line 1.

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