Will I be charged capital gains tax on Bitcoin I sold and rebought on Cash App?

Thanks for the answer but that really sucks. So even though I never actually took any money out of the app, I'll still owe taxes? How do I calculate what I'll owe? My total investment was around 40k and now it shows I made all these "profits" that I never actually realized.

Each sale is a separate taxable event, regardless of whether you withdrew the funds or not. What matters is your cost basis (what you originally paid) versus what you sold it for. To calculate what you'll owe, you'll need to determine your gain on each sale. For example, if you bought Bitcoin at $30k and sold at $80k, that's a $50k gain. The tax rate depends on your holding period and income bracket - anywhere from 0-20% for long-term gains or your ordinary income rate for short-term gains. Cash App should provide you with a tax document (Form 1099-B) showing your transactions, which will help with your calculations.

Does it work with Cash App specifically? I've got a similar situation but with like 40+ trades and I'm freaking out about tax season.

I'm skeptical of these crypto tax services. How do they handle the basis calculation when you've bought at different price points? My situation is messy with Bitcoin purchased across 3 platforms at various times.

Yes, it works with Cash App and most other major platforms. It can either connect directly or you can upload your transaction history. With 40+ trades it would definitely save you a lot of manual calculation headaches. Regarding basis calculations across multiple platforms, that's actually where it really shines. It uses FIFO (First In, First Out) by default, but you can switch to other accounting methods like LIFO or specific identification if that works better for your situation. I had Bitcoin spread across Coinbase, Cash App and a hardware wallet, and it consolidated everything correctly to determine my true cost basis for each sale.

How does this actually work? The IRS phone system is literally designed to keep you on hold forever. Is this legit or just another scam?

No way this actually works. I've tried calling the IRS three times this month and couldn't get through. If they actually had some magical way to skip the queue, the IRS would shut it down immediately. Sounds like a waste of money to me.

It's not a queue-skipping service in the way you might think. They use an automated system that navigates the IRS phone tree and waits on hold for you. When an agent actually picks up, you get a call back to connect with them. It's completely legitimate - they're just doing the waiting for you. I was skeptical too, but it absolutely worked. I spent weeks trying to get through on my own with no luck. With Claimyr, I had an IRS agent on the phone discussing my crypto tax situation within about 15 minutes of starting the process. No magic involved - just technology handling the frustrating hold times.

Do wash sale rules apply to crypto? I thought I read somewhere that they don't, which would mean you could sell at a loss and rebuy immediately to harvest the tax loss?

As of the 2025 tax year, crypto is still not subject to wash sale rules that apply to stocks and securities. This means you can indeed sell crypto at a loss and immediately rebuy it to harvest the tax loss, unlike with stocks where you'd have to wait 30 days. However, always be careful with tax strategies like this and consider consulting a tax professional. The IRS has been increasing their focus on crypto compliance, and rules can change. Make sure you're documenting everything carefully in case of questions later.

I used TurboTax last year for my crypto and it was ok for basic stuff, but got REALLY confusing with multiple platforms. Had to manually enter a ton of transactions. If you have more than like 10-15 trades, I'd recommend a specialized crypto tax software instead.

Thanks for sharing your experience! That's really helpful to know. I probably have about 25-30 transactions so I think I'll look into one of the specialized options mentioned in this thread instead of struggling with manual entry.

Thanks for the heads up. I definitely want to report everything correctly. Better to pay what I owe than deal with an audit. Seems like I need to get organized with all my transactions before filing.

No problem! And yeah, being organized is key. Since you used Cash App, you should be able to download your full transaction history as a CSV file. Save this along with any tax forms they provide. If they don't give you detailed enough info, you can always request your account history directly. Remember that crypto exchanges are increasingly reporting to the IRS directly, so your transactions are likely already on their radar. Being proactive and thorough in your reporting is definitely the way to go.