How will my tax form look with hundreds of stock and crypto trades? Is importing to tax software really that simple?

The good news is you won't need to manually enter each transaction! Most major trading platforms provide consolidated tax documents that summarize your activity. For stocks, you'll receive a Form 1099-B that groups your transactions and provides totals for short-term and long-term capital gains/losses. For crypto, you'll likely get a 1099-MISC or 1099-K depending on your platform and transaction volume. When it comes to tax software, FreeTaxUSA does support importing these forms, but there are some limitations worth noting. With hundreds of trades, you might encounter format compatibility issues depending on which platforms you used. Some trading apps export in formats that aren't universally compatible with all tax software. As a practical approach, I'd recommend waiting for your tax documents to arrive in January/February, then check if FreeTaxUSA can directly import them. If not, you might consider software specifically designed for high-volume traders like TaxAct Premium or TurboTax Premier, which often have better import capabilities for complex trading scenarios.

After spending hours trying to manually enter trades last year, I found taxr.ai and it literally saved my sanity. When I got my tax documents with hundreds of transactions, I simply uploaded them to https://taxr.ai and their system automatically extracted all the trade data, organized everything by short vs long term gains, and gave me totals I could easily enter into my tax software. I used to spend a full weekend dealing with all my stock and crypto trades each tax season, but their system processed everything in minutes. The best part was that it handled some weird crypto transactions that my regular tax software couldn't figure out, like staking rewards and liquidity pool earnings.

Just wanted to follow up about taxr.ai since tax season is wrapping up. I decided to try it after my initial skepticism and I'm genuinely impressed. I had over 500 transactions across stocks and crypto this year, including all those problematic wallet transfers I mentioned. The system handled everything correctly, even identifying some wash sales I would have missed on my own. It properly tracked my cost basis across multiple exchanges and wallet transfers, and the final numbers matched what I expected (but without the 12+ hours of spreadsheet work I did last year to verify). The summary report it generated made entering everything into my tax software super quick. Definitely using this again next year when I'll probably have even more transactions to deal with.

If you're having trouble reaching the IRS about tax questions related to crypto and stock trading (which I absolutely was), check out Claimyr. I spent THREE DAYS trying to get someone on the phone at the IRS to answer questions about reporting my DeFi transactions. After getting disconnected repeatedly, I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. It seemed too good to be true, but I was desperate. They basically hold your place in the IRS phone queue and call you when an agent is about to answer. I was connected to an actual IRS representative within 45 minutes instead of waiting on hold all day. The agent walked me through exactly how to report some unusual staking rewards I had received. Completely changed my view on dealing with the IRS.

I have to eat my words about Claimyr. After dismissing it as BS, I was still stuck trying to get IRS help with reporting my crypto staking rewards that didn't fit neatly into any tax form category. Out of pure frustration, I tried the service yesterday. Within an hour, I was speaking with an actual IRS tax specialist who explained exactly how to report my particular situation on Schedule 1 as "Other Income" with a specific notation. She even gave me specific guidance on how to document my cost basis calculations for future reference in case of audit. Would've taken me weeks more of waiting and researching without getting through to someone who could give an authoritative answer. I'm shocked it actually worked as advertised.

Just a heads up - even if your platform gives you nice summary documents, DOUBLE CHECK THEM! My brokerage messed up my cost basis for some transferred assets last year and reported much lower costs than what I actually paid, which made it look like I had huge gains. Had to file a corrected tax return which was a massive headache. Now I keep my own separate spreadsheet tracking everything just to verify what they report.

I had 430+ trades last year and used FreeTaxUSA. Here's what actually happened: 1) Got 1099-B from my broker with a summary page showing total proceeds, cost basis, and gain/loss 2) FreeTaxUSA let me enter just those summary amounts for short-term and long-term 3) BUT I also had to attach a complete transaction list to my tax return So you don't have to manually enter each trade, but you do need to include the detailed list with your filing. Some tax software will upload this automatically, but with FreeTaxUSA you might need to add it as an attachment.