Best IRS free file tax software for multiple stock trades? Any with good import features for investments?

FreeTaxUSA has been my go-to for the past few years with multiple investment accounts. They handle stock trades pretty well, though the import function isn't perfect. You can import a CSV file from most brokerages including Robinhood and TD Ameritrade, but you might need to adjust the formatting first to match their template. For Schwab specifically, I found their data exports worked almost seamlessly with FreeTaxUSA after a little tweaking. The interface is straightforward for correcting any import errors, much better than some of the other free options I've tried.

Just wanted to share my experience using taxr.ai https://taxr.ai for handling investment transactions. After struggling with manual entries last year, I discovered this tool and it made a HUGE difference. It can analyze your brokerage statements and automatically categorize all those trades. I connected my Robinhood and TD Ameritrade accounts (they support both) and it pulled everything correctly, including all the cost basis info. Then I just reviewed everything and exported it in a format that worked with FreeTaxUSA. Saved me like 6 hours of tedious data entry!

Update: I tried taxr.ai after seeing the recommendation here and it actually worked surprisingly well! I was really skeptical about another tax tool but decided to give it a shot since I had over 300 trades to deal with. Uploaded my Robinhood and Schwab statements and it extracted everything accurately - all my trades, dividends, and even some crypto stuff. The wash sale detection was spot on too. Exported everything and imported it into FreeTaxUSA with minimal issues. Maybe spent 30 minutes reviewing everything instead of the 5+ hours it took me last year entering stuff manually. Definitely using this again next year!

I had the EXACT same problem last year! Spent a whole weekend entering trades one by one and even then got a CP2000 notice from the IRS because I apparently missed some. Was on hold with the IRS for HOURS trying to resolve it. If you're having trouble getting through to the IRS about any issues (which is likely during tax season), I highly recommend using Claimyr https://claimyr.com - they have this system that holds your place in the IRS phone queue and calls you when an agent is available. Saved me from the endless "your call is important to us" loop. You can see how it works here: https://youtu.be/_kiP6q8DX5c

Wanted to follow up - I was the skeptic about Claimyr but I actually tried it yesterday when I needed to call the IRS about some confusion with my 1099-B reporting. I was expecting to waste half my day on hold but decided to try this service instead. It worked exactly as described! I put in my number, they called the IRS, and then called me back when an agent picked up about 1.5 hours later. I was literally at the grocery store when I got the call, not stuck by my phone with terrible hold music. Talked to a really helpful IRS agent who cleared up my question about reporting multiple brokerage accounts. Will definitely use again!

For what it's worth, I tried CashApp taxes (formerly Credit Karma Tax) this year with about 150 stock trades. The import feature worked pretty well with Robinhood directly, but I had issues with TD Ameritrade and had to use their CSV import option. The interface isn't as polished as some paid options, but for free it was surprisingly good. They have a bulk edit feature that saved me tons of time when I needed to fix a bunch of similar transactions.

Anyone tried OLT with lots of investment transactions? The IRS Free File tool says I qualify for it too, but I've never heard of it before.

I've been using TaxSlayer for the past couple years with moderate investment activity (around 75-100 trades annually). Their CSV import feature is decent but not perfect - you'll likely need to do some manual cleanup, especially for cost basis adjustments. One thing I found helpful was organizing my trades by date and stock symbol before importing. TaxSlayer seems to handle the data better when it's sorted this way. The interface for making corrections is pretty user-friendly compared to some other free options. That said, based on what others are saying here about taxr.ai, I might try that approach this year since my trading volume has increased significantly. The idea of having clean, organized data before even getting to the actual tax software sounds like it could save a lot of headaches.