How do I claim capital gains losses from previous years on my 2025 tax return?

But what if the filing deadline has passed for those years? Would OP need to file amended returns instead? And is there a limit to how much of the carryover loss they can use each year against regular income?

You don't file amended returns if you never filed in the first place - you'd just file regular returns for those previous years, even though they're late. The IRS generally allows you to file returns and claim refunds for up to three years after the original due date, so 2021 and 2022 are still within that window. For your second question, there is a limit on how much capital loss you can claim against ordinary income in a single year - it's $3,000 ($1,500 if married filing separately). Any excess beyond that amount gets carried forward to future years. However, capital losses can offset capital gains without this limitation.

Wait, how does this service work with capital loss carryovers? Does it actually help you file the previous years' returns or just calculate the numbers for you? I have a similar situation with some failed investments from 2021-2023.

I'm curious - does taxr.ai handle crypto losses too? I've got a complete mess of transactions across multiple platforms and I've been putting off dealing with it for years because it seems so complicated.

The service analyzes all your investment documents and generates the completed tax forms you need for each tax year, showing exactly what your capital losses were. They don't file the returns for you, but they prepare all the documents so you can easily file them yourself. It saved me a ton of time figuring out basis calculations. Yes, they absolutely handle crypto transactions! That's actually where they really shine. You can connect your exchanges or upload transaction records, and their system sorts through everything, handles all the complex basis calculations, and prepares the right tax forms. It saved me from the nightmare of manually tracking hundreds of crypto trades.

How does this actually work? The IRS phone lines are notoriously impossible to get through. Are you saying this service somehow gets you to the front of the queue?

This sounds like BS honestly. No way some third-party service can magically get through IRS phone lines when millions of people can't. They probably just keep autodialing until they get through and charge you a fortune for it.

It actually works by using an automated system that navigates the IRS phone tree and waits on hold for you. When an agent picks up, you get a call back connecting you directly to them. No line cutting - they're just doing the waiting for you. It's definitely not BS. I was skeptical too but it legitimately works. They use technology to handle the hold queue so you don't have to waste hours with your phone pressed to your ear. The service costs less than what I was losing in productivity trying to call the IRS myself repeatedly.

Do you know if there's a dollar threshold where getting professional help makes more sense? My losses were around $8,500 total across those two years. Not sure if that's enough to justify paying for professional help or if I should just attempt to handle it myself with tax software.

There's no specific dollar threshold that makes professional help necessary - it really depends on the complexity of your situation more than the amount. For $8,500 in straightforward capital losses from typical investments or crypto trading, tax software should handle it fine. The time you'd want professional help is when you have unusual situations like crypto mining equipment (which might be Section 179 property rather than capital assets), business investments, or complicated basis calculations. If you're just dealing with losses from buying and selling investments, the standard tax software options should guide you through it correctly.

Any recommendations for good ways to organize tax documents? I'm terrible at keeping track of paperwork and now I'm worried about this exact scenario.

I use a simple digital filing system - scan or photograph all tax documents and store them in folders by year (like "2021 Tax Docs", "2022 Tax Docs", etc.). I keep both the originals in a physical file and digital copies in cloud storage like Google Drive or Dropbox. For capital losses specifically, I also maintain a separate spreadsheet tracking my carryforward amounts year by year so I don't have to dig through old returns to remember what I'm carrying forward. Takes about 10 minutes after I file each year but saves hours if the IRS ever comes asking questions.