Do I need to mail Form 8453 with my stock trading Form 8949 and Schedule D?

You're right to double-check this! When you have a large number of stock transactions, you have two options: First, you can enter each transaction individually into TurboTax, which is tedious but means everything is submitted electronically. Second, you can send summaries of your transactions on Form 8949 and Schedule D electronically, but then you need to mail Form 8453 as a transmittal document along with your detailed trading records. This is because the IRS still wants to have your complete transaction history available if needed. And yes, the IRS does require you to mail Form 8453 with your supporting documents within 3 business days of your electronic return being accepted. However, if your e-file is accepted on April 17th and you mail Form 8453 by April 19th, you'll be fine! The important date is when you e-filed, not when the supporting documents are mailed. As long as you mail within that 3-day window, you've complied with the requirements.

I was in exactly your situation last year! I had over 200 stock trades and was totally overwhelmed trying to enter them all manually in TurboTax. After hours of frustration, I found this tool called taxr.ai (https://taxr.ai) that saved me so much time. It basically analyzes all your trading documents and helps organize everything properly. I just uploaded my brokerage statements and it sorted everything out - even identified which ones needed to be reported on 8949 and which could be summarized. It also gives clear instructions about which forms need to be mailed vs. e-filed. The best part was that it flagged a bunch of wash sales I would have missed on my own. Definitely made the whole process way less stressful!

I was initially skeptical about taxr.ai, but I decided to try it when I realized my brokerage statements weren't properly identifying wash sales across multiple accounts. Honestly, it was a game-changer! The tool flagged several issues my broker missed and saved me from a potential audit. The Form 8453 situation was actually explained perfectly - it showed exactly which forms needed to be mailed versus e-filed, and gave me a checklist to make sure I didn't miss anything. I was able to e-file the main return and mail just the required supporting documents with confidence. Would definitely recommend if you're dealing with multiple accounts or complex trading activity!

If you're struggling with getting your trading paperwork filed correctly, just wait until you try reaching the IRS with questions! I spent THREE DAYS trying to get through to a human at the IRS about a similar Form 8453 question last year. Busy signals, disconnects, and hours on hold. Finally found Claimyr (https://claimyr.com) which somehow got me through to an actual IRS agent in about 20 minutes. They have this whole system that navigates the IRS phone tree and holds your place in line, then calls you when an agent is available. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent confirmed that I just needed to mail the 8453 with my detailed transaction records within 3 days of e-file acceptance, and that the postmark date is what counts. Saved me so much stress!

I need to eat my words. After my skeptical comment, I was still stuck with a question about Form 8453 that no one could answer, so I reluctantly tried Claimyr. Within 35 minutes (while I was grocery shopping), I got a call connecting me directly to an IRS representative. The IRS agent clarified everything about my Form 8453 question and even helped me understand exactly which records needed to be attached. Turns out I was overthinking it - I just needed to include the summary statements from my brokerage, not every single transaction receipt. Still can't believe I wasted 4 hours on hold the week before when this service could have saved me all that time. Definitely using it again next time I have IRS questions.

Another option nobody mentioned - if you're using TurboTax, you can actually import your stock transactions directly from many brokerages. I have accounts with Fidelity and was able to import everything automatically. This way your return is fully electronic with no need to mail anything. You just need to connect TurboTax to your brokerage account through their secure connection. It pulls all the transactions and categorizes them properly. Saved me hours of data entry!

Quick tip from someone who's dealt with this exact situation for years: When you mail your Form 8453 package, write your Social Security number on EVERY page of the attached trading records. Also include a copy of your Form 8949 and Schedule D that you e-filed. The IRS processes these attachments separately from your electronic return, and having your SSN on each page helps ensure everything stays together and gets associated with your return correctly.