I've heard that I do not need to send a 1099-MISC to a contractor if I paid them through PayPal, even if they made more than $600. Is this correct?
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Yes, you are correct that you do not need to send Form 1099-MISC.
According to the IRS Instructions for Form 1099-MISC, "Payments made with a credit card or payment card and certain other types of payments, including third-party network transactions, must be reported on Form 1099-K by the payment settlement entity under section 6050W and are not subject to reporting on Form 1099-MISC. See the separate Instructions for Form 1099-K."
In short, PayPal will issue Form 1099-K to your contractor. So you do not need to send Form 1099-MISC.
There are two choices in sending money: to a friend, to pay for services. Is the answer the same? I believe I have sent money via friend by mistake (the new dashboard no longer offers a clear choice). So far its only a $300 but could go over the $600.
A second question - if i pay someone $1000, then how does PayPal not sending anything until its over $20k remove me of the obligation to file a 1099?
Your question was posted to a an old thread that has a real mish-mosh of questions about PayPal, 1099"s etc. that may or may not be relevant to your own issue. It would be better for you to re-post your question as a brand new fresh thread --in which you are more specific about your situation. You do not say here why you paid your friend. You did not say if you have a business yourself or if you just paid a buddy for helping you do something around your home, etc. We need more information.
How about payment via Zelle$?
@wiseman Please read the reply directly above your own post.
What about the fees I incurred when sending funds via Family and Family option on PayPaL? Can I include the fees on the 1099 sent to the contractor? He requested that I use this method to pay him. The fees were for his benefit, can I pass the amt on to the contractor?
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