https://community.squareup.com/t5/Staff-Payroll/Can-I-pay-a-contractor/m-p/666876#M1571 <P>you can... but you do need to wait some time (maybe 30 minute) or else the system will think it is a duplicate payment.&nbsp;</P> Tue, 20 Jun 2023 20:13:52 GMT DinaLRosenberg 2023-06-20T20:13:52Z https://community.squareup.com/t5/Staff-Payroll/Can-I-pay-a-contractor/m-p/666870#M1570 <P>Can you pay the same 1099 contractor twice in one day?</P> Sun, 21 Sep 2025 06:34:54 GMT https://community.squareup.com/t5/Staff-Payroll/Can-I-pay-a-contractor/m-p/666870#M1570 Pawtenders 2025-09-21T06:34:54Z https://community.squareup.com/t5/Staff-Payroll/Can-I-pay-a-contractor/m-p/666876#M1571 <P>you can... but you do need to wait some time (maybe 30 minute) or else the system will think it is a duplicate payment.&nbsp;</P> Tue, 20 Jun 2023 20:13:52 GMT https://community.squareup.com/t5/Staff-Payroll/Can-I-pay-a-contractor/m-p/666876#M1571 DinaLRosenberg 2023-06-20T20:13:52Z