I found posts on reddit where a cashapp rep was telling people they would receive a 1099-b if they transferred the coin off the wallet also. That being said, I have been unable to confirm that fact through their support or with anyone who has gotten a tax form from them this tax season.  I'd rather not fool with taxes at all at this point since they don't show the cash basis on their app at all.

This all I could get out of them when asking about their handling of bitcoin taxes.  I am guessing they don't send anything unless you sell on their app, but I have yet to get any concrete information on this.

Im Benjamin, and I'm with Cash Support; thanks for taking the time to reach out to us about the potential tax documents you may receive as part of using our investing tools. Let me explain what you can expect!

Cash App will provide an annual 1099-B to Cash App customers who have made a sale of bitcoin during the calendar year. To learn more about the 1099-B tax reporting and bitcoin, visit our Support Center.

In order to calculate your taxable gains and losses, please refer to your account activity history in Cash App. Cash App does not report a cost basis for your Bitcoin sales to the IRS.

Cash App does not provide tax advice. If you have questions about your particular tax situation you should consult a tax advisor. This is not tax advice.

How would they list proceeds on a 1099 if you just transfer the coins to another wallet?  Seems like they would not have enough information to generate a form.  Their support is non existent, so I am pretty much regretting using them.  They do make it relatively easy to get bitcoin though and don't have massive fees.  As least coinbase makes it pretty clear how they handle reporting with 1099k being sent only to those meeting certain thresholds.

Happen to be anyone on this site who has used CashApp for Bitcoin purchases and can shed some light on the process they use to generate 1099-b forms?   There site says they will issue a 1099-b for anyone who "sells" coin on their app, but I have also seen they generate a form for anyone who just buys it and then transfers it to another wallet. Seems very confusing to me, so any help would be appreciated.