Yes. I just received my 1099-B for 2023 from CashApp. Every time I sold BTC, CashApp considered the amount you sold in BTC as capital gains. So yes, you will owe federal taxes each and every time you sell BTC for USD because they recognize this as income.
It kind of sucks because they are taxing me on the entire amount of BTC I sold in 2023. (I’m just going to use round numbers to explain the 1099-B form CashApp sent me.)
In 2023, I sold $5,000 worth of Bitcoin through CashApp to receive 5,000 USD to deposit into my Chase checking account. CashApp then sent me a 1099-B form for the year of 2023. They are considering the entire $5,000 worth of BTC that was sold as “capital gains,” regardless of where the BTC originated from or how you obtained it. To make a long story short, you will have to pay federal taxes on ANY Bitcoin you sell through CashApp.
JJ