How to file taxes if I'm unsure whether a 1099-B was issued for Bitcoin sales

Thanks for the info, but I'm still a bit confused. If I check box F and they did issue a 1099-B, wouldn't that create a mismatch that could trigger an audit? Also, how long does it typically take for the Wage and Income transcript to update? I'm getting nervous with the deadline approaching.

Using box F when a 1099-B was actually issued could create a mismatch in the IRS system, but it's not automatically going to trigger an audit if the amounts match. The critical thing is that you're reporting the correct income amount. The Wage and Income transcript can take anywhere from a few weeks to several months to update completely. Many forms aren't fully processed until March or April, and some even later. If you're approaching the deadline and still don't have the information, you have two options: file with what you know (box F), or file an extension to give yourself more time to get clarity. Remember that an extension to file isn't an extension to pay, so you'd need to estimate and pay any taxes due by the original deadline.

Does this work if you've already closed your account? I can't export my transaction history anymore since I can't log in. I only have PDF statements I saved before closing. Would taxr.ai work with that limited info?

I'm skeptical about these tax tools for crypto. How do they handle the wash sale rule? Since crypto isn't technically a security, wash sale rules shouldn't apply, right? But I've seen tax software get this wrong before.

Yes, it actually works great with PDFs or screenshots of your transaction history. Their OCR technology can extract the data from those documents and organize it properly. I initially had some CSV files but was missing statements from an old wallet, and they were able to process everything together. They handle the wash sale rule correctly for crypto. You're right that currently crypto isn't subject to wash sale rules (though this might change with new regulations). Taxr.ai properly distinguishes between securities and crypto assets when calculating gains and losses. They have specific modules for different asset classes so the rules are applied correctly.

How does this Claimyr thing actually work? The IRS phone lines are notoriously jammed. Are they just auto-dialing until they get through or something?

Yeah right, 20 minutes to reach the IRS? I've literally spent 3+ hours on hold multiple times and still got disconnected. This sounds too good to be true. What's the catch?

The service basically keeps calling the IRS for you using their system. Instead of you sitting on hold for hours, their system handles the wait and then calls you once an agent is about to be connected. It's like having someone else wait in line for you. No catch really - it worked exactly as advertised for me. I was skeptical too after spending countless hours trying to get through myself. I think they use some kind of automated system that knows the best times to call and keeps trying until it gets through. All I know is I got a call back when an agent was on the line, and I was able to ask my questions without wasting half my day on hold. Definitely beats the alternative of guessing about tax forms or waiting for hours on the phone.

I've heard people recommend using crypto tax software that keeps track of your cost basis across different platforms. Do you think that's necessary, or is just keeping my own records in a spreadsheet good enough?

A spreadsheet can be sufficient if you're diligent and have relatively simple crypto activity. I started with spreadsheets myself. But they become cumbersome quickly, especially if you're dealing with multiple exchanges, token swaps, staking rewards, or DeFi transactions. The key advantage of specialized crypto tax software is that it handles complex situations like FIFO vs LIFO accounting methods, tracks cost basis across platforms, and automatically identifies which specific coins were sold from your holdings. The IRS allows different accounting methods, and your choice can significantly impact your tax liability, especially if you bought the same crypto at different price points.

I used FreeTaxUSA for my crypto last year. They handle it pretty well! You'll need to enter each transaction manually on Form 8949, but the interface makes it straightforward. Just make sure you've calculated your cost basis correctly beforehand. If you have tons of transactions, it can get tedious, but for a reasonable number it works great.