Does FreeTaxUSA allow attaching supporting files for 1099B transactions?

Yes, FreeTaxUSA does allow you to attach PDF files to your return, which is helpful for supporting documents like your 1099B. This is one of the advantages of their platform compared to some others. When you're entering your investment income in FreeTaxUSA, you'll reach a point where you can choose to enter summary information instead of listing each transaction individually (similar to what you've been doing in TurboTax). The difference is that FreeTaxUSA will give you an option to upload PDFs of your supporting documents with your e-filed return, so you won't need to mail anything. Just make sure your PDFs aren't too large as there are file size limits. I typically scan my documents at a lower resolution to ensure they're accepted.

I switched from TurboTax to FreeTaxUSA last year because I was tired of paying those ridiculous fees. I had to file a Schedule D with literally hundreds of crypto transactions and was facing the same issue with attaching my documentation. Check out https://taxr.ai - it saved me hours of headache by extracting all my transactions from my messy 1099Bs and brokerage statements. Their system can read all your tax documents and convert them into a format that's way easier to work with. Then you can either enter the data yourself or import it into most tax software including FreeTaxUSA.

Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it actually worked amazingly well for my crypto nightmare! Uploaded my transaction records from Coinbase, Binance and Kraken, and it extracted everything perfectly. Then I was able to bring that organized info right into FreeTaxUSA without having to manually enter 50+ transactions. The best part was that FreeTaxUSA let me attach the original statements as PDFs so I didn't have to mail anything. Saved me HOURS of work and probably kept me from making mistakes with all those numbers.

If you're having issues with the IRS receiving your documents or need clarification about attachment requirements, good luck trying to call them directly. I spent literally 4 hours on hold last year trying to figure out if my mailed 1099B documents were received. I discovered https://claimyr.com which basically holds your place in the IRS phone queue and calls you when an agent is about to answer. You can see how it works here: https://youtu.be/_kiP6q8DX5c I ended up getting a callback in about 45 minutes rather than waiting on hold all day. The IRS agent confirmed that electronic attachments through FreeTaxUSA are perfectly acceptable and actually preferred over mail.

Update: I was super skeptical about Claimyr but I just used it yesterday to ask the IRS about my 1099B situation. I couldn't believe it actually worked! Got a call back in about an hour when I was expecting to waste my entire afternoon. The IRS rep confirmed that filing with FreeTaxUSA and attaching PDFs electronically is actually their preferred method for handling 1099B summary info. They said mailed documents can take 6-8 weeks to process while electronic attachments are available to them immediately. Definitely going the FreeTaxUSA route next year.

Been using FreeTaxUSA for 3 years now after spending way too much on TurboTax. A few tips on the document attachment feature: 1. They have a 15MB total limit, so compress your PDFs if needed 2. You can attach at multiple points during the filing process, not just for 1099Bs 3. Name your PDFs clearly before uploading (like "1099B_Fidelity_2024.pdf") 4. You can actually attach explanations for unusual tax situations too The interface isn't as fancy as TurboTax but it's way more affordable and has all the features most people need.

I've tried both TurboTax and FreeTaxUSA, and honestly, for most people FreeTaxUSA is the better choice just based on cost alone. The federal filing is free and state is only like $15 compared to TurboTax charging $100+ for anything beyond the most basic returns. One thing to note about document attachments - they're sent to the IRS but not necessarily reviewed immediately. Think of them as backup documentation in case of an audit rather than something they'll check right away. Still way better than mailing though!

This thread has been incredibly helpful! I'm in the exact same boat as Carmen - dealing with messy 1099B imports in TurboTax and facing the mail-in documentation requirement again this year. Based on what everyone's shared, it sounds like FreeTaxUSA could solve multiple problems: electronic document attachments, free federal filing even with investments, and no more trips to the post office. The 15MB limit and PDF compression tips from Giovanni are especially useful to know upfront. I'm definitely going to give FreeTaxUSA a try next year. Between the cost savings and the convenience of electronic attachments, it seems like a no-brainer compared to paying TurboTax's inflated fees just to end up mailing documents anyway.