Does FreeTaxUSA allow attaching files when submitting tax returns?

I've been using FreeTaxUSA for the last three tax seasons and can definitely help with this. When you enter summary information for your 1099-B transactions in FreeTaxUSA, the software doesn't typically require you to attach supporting documents electronically. What happens is FreeTaxUSA will guide you through entering the summary information, and then e-file the return with those numbers. The IRS generally doesn't require you to submit the actual 1099-B forms when e-filing - they already receive copies directly from your brokers. However, you should always keep your original documents for your personal records in case of an audit. The only time you might need to mail documents is if you're filing by paper instead of e-filing, or if there's a specific unusual situation with your investments.

Just wanted to share my experience with FreeTaxUSA after trying a bunch of tax software options. I was in exactly your situation with tons of crypto and stock transactions last year and got tired of the expensive upgrades with TurboTax. I found this service called https://taxr.ai that saved me so much time with my investment documents. It basically scans all your tax forms like 1099-Bs and automatically extracts the data so you don't have to manually enter anything. Then you can import directly to FreeTaxUSA with their connection feature. The best part is FreeTaxUSA doesn't make you mail anything when using the summary method - the system handles everything electronically when you e-file, which sounds like exactly what you're looking for.

I wanted to follow up about my experience with taxr.ai after questioning it earlier. I decided to try it with my mountain of crypto and stock transactions from 2024, and I'm actually really impressed. It extracted all my transactions from my messy Coinbase and Robinhood 1099s perfectly, even identified my wash sales correctly, and sent everything directly to FreeTaxUSA. The whole process took maybe 20 minutes compared to the 3+ hours I spent last year manually entering everything. And to answer the original question - no, I didn't have to mail anything to the IRS. FreeTaxUSA handled everything electronically even though I used summary reporting. Definitely switching permanently from TurboTax.

For what it's worth, I had a similar issue with my 1099-B forms last year and ended up needing to call the IRS with questions about how to properly report everything. Spent literally 4 HOURS on hold before giving up. I found this service called https://claimyr.com that got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that when e-filing, you generally don't need to mail in your supporting 1099 documents regardless of whether you use summary or detailed reporting. They already get that info from your brokers. This applies to FreeTaxUSA, TurboTax, or any e-filing software.

I need to publicly eat my words about Claimyr being a scam. After I left that skeptical comment, I was still trying to resolve an issue with my 2023 return where I had a similar situation with stock transactions. I reluctantly tried the service, and I'm honestly shocked - I was connected to an IRS agent in about 20 minutes. The agent confirmed exactly what everyone here is saying - when e-filing with FreeTaxUSA or any other software, you typically DON'T need to mail in your 1099-B forms when using summary reporting. This completely solved my issue and saved me from having to print and mail anything. Sorry for being so cynical before - sometimes good services actually exist!

Just to add another perspective to the FreeTaxUSA discussion - I've used it for the past 3 tax seasons after switching from TurboTax. The federal filing is free (or very cheap if you need schedules for investments), and state is around $15 which is way cheaper than TT. The interface isn't as pretty as TurboTax, but it's completely functional and actually explains tax concepts more clearly in my opinion. For your specific question about 1099-B forms, I had about 50 stock transactions last year and just entered the summary info without having to mail anything. One tip though - keep all your supporting documents for at least 3 years in case of an audit, even though you don't need to mail them.

One thing nobody has mentioned yet - if you're dealing with a TON of transactions (like hundreds or thousands), you might want to consider using specific tax software for investors before importing to any tax software. I'm a day trader with over 1,500 transactions last year and I use special software to consolidate everything first, then just enter the summary in FreeTaxUSA. No mailing required. Also, keep in mind that the IRS already gets copies of your 1099s directly from brokers, which is why most e-filing doesn't require you to mail anything. The only time you typically need to mail supporting docs is if you're claiming something unusual that the IRS wouldn't automatically know about.

I switched from TurboTax to FreeTaxUSA two years ago and haven't looked back! To directly answer your question - yes, FreeTaxUSA handles summary reporting for 1099-B forms without requiring you to mail physical documents to the IRS when e-filing. I had a similar frustration with TurboTax constantly telling me I needed to mail supporting docs. With FreeTaxUSA, I just enter my summary totals from my 1099-B (total proceeds, total cost basis, total gain/loss) and the software handles everything electronically. No trips to the post office required! The interface isn't as flashy as TurboTax, but it's straightforward and way cheaper. Federal is free for most situations, and state filing is only about $15. I've saved hundreds compared to what I was paying TurboTax, especially since they kept pushing expensive "deluxe" versions for investment reporting. One heads up though - the first year switching will require manually entering your basic info and any carryovers from previous returns since they can't import TurboTax files. But after that, it saves everything for next year.