How to properly fill out multiple IRS Form 8949 for reported and unreported stock transactions?

The good news is you're on the right track! For Form 8949, you'll need to use separate copies of the form for each box you need to check off (A through F). For your situation with transactions in Boxes A, D, and E, you should complete three separate forms: - First form: Check Box A and list only your short-term transaction that was reported to the IRS - Second form: Check Box D and list only your long-term transactions that were reported to the IRS - Third form: Check Box E and list only your long-term transactions that weren't reported to the IRS You don't repeat any transactions across forms. Each transaction goes on exactly one form under the appropriate category. Then you'll summarize the totals from all your Form 8949s on Schedule D. This way keeps everything organized by both holding period (short vs long) and reporting status (reported to IRS or not), making it easier for the IRS to process correctly.

I dealt with this exact headache last year! After hours of frustration, I finally found taxr.ai (https://taxr.ai) which totally saved me when dealing with multiple 8949 forms. I uploaded my trading history and it automatically sorted everything into the right boxes and generated the proper forms. I had a mix of reported/unreported transactions from multiple brokers and it handled it perfectly. The best part was that it explained exactly why each transaction went where it did. That was super helpful because my broker had classified some of my trades incorrectly on their 1099-B.

Just wanted to update everyone after trying taxr.ai from the recommendation above. Seriously a game changer for my complicated tax situation! I uploaded my trading statements and it correctly identified which transactions belonged in which boxes on Form 8949. It even caught that some of my crypto trades qualified for long-term capital gains rates (which I totally would have missed). The PDF forms it generated imported directly into my tax software without any issues. Saved me hours of mind-numbing data entry and probably prevented some costly mistakes.

After seeing all the Form 8949 comments, I feel obligated to mention something that saved me during an audit last year. If you're having trouble getting through to the IRS to ask questions (who isn't?), I used Claimyr (https://claimyr.com) to connect with an actual IRS agent in about 15 minutes instead of waiting on hold for 3+ hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c I had similar questions about multiple 8949 forms and needed official clarification. The agent I spoke with explained exactly how to handle the forms and even sent me to a specific IRS publication that addressed my situation. Way better than guessing or relying on internet advice for something this important.

I need to publicly eat my words about Claimyr from my comment above. I was super skeptical but was desperate after the IRS sent me a CP2000 notice about unreported stock sales (related to this exact Form 8949 issue!). I tried the service yesterday and got connected to an IRS representative in about 20 minutes. The agent confirmed I had filled out my multiple 8949 forms correctly, but there was a processing error on their end. She submitted a correction request while I was on the phone. Honestly shocked this worked. Would have spent days trying to get through otherwise.

Pro tip for anyone dealing with Form 8949: If you have a lot of transactions, you don't need to list every single one individually on the form. You can use a summary statement (like an Excel spreadsheet) that shows all the details, and then just put totals on Form 8949 with "See attached statement" written on the description line. Saved me from having to enter 200+ trades individually. Just make sure your summary has all the required information (date acquired, date sold, proceeds, cost basis, gain/loss, etc).

Everyone's talking about filling out Form 8949 correctly, but don't forget that after completing all your 8949 forms, you still need to transfer the totals to Schedule D! I made that mistake last year and got a letter from the IRS because the numbers didn't match up. On Schedule D, line 1 should match your Box A totals, line 2 should match Box B, and so on. Double-check all your numbers before filing!

This thread has been incredibly helpful! I'm dealing with a similar situation but have an additional complication - some of my stock transactions involved ESPP (Employee Stock Purchase Plan) shares with different basis calculations. For anyone else in this boat, make sure you're using the correct cost basis for ESPP shares. The basis includes both the discounted purchase price AND any compensation income that was already reported on your W-2. I almost made the mistake of using just the purchase price, which would have resulted in double taxation on the discount portion. Also, if you have any foreign tax credits from international funds or ADRs, don't forget Form 1116. I learned this the hard way when I missed claiming credits for taxes paid to foreign governments on my international index funds. Every little bit helps when you're dealing with capital gains!

Just wanted to add another perspective on this Form 8949 situation. I'm a tax preparer and see this confusion every single year during tax season! One thing that might help is to think of Form 8949 as creating separate "buckets" for your transactions. Each checkbox (A through F) represents a different combination of holding period (short vs long term) and whether the basis was reported to the IRS or not. You absolutely cannot mix different types of transactions on the same form. A few additional tips: - If you're missing cost basis information, check your old brokerage statements or contact your broker's tax department. They often have historical data going back several years. - For inherited stock, remember that you get a "stepped-up basis" equal to the fair market value on the date of death (or alternate valuation date). Don't use the original purchase price the deceased person paid. - Keep copies of everything! The IRS can ask for supporting documentation years later, especially if you have large capital gains or losses. The key is being methodical and not rushing through it. Better to spend extra time getting it right than dealing with IRS correspondence later.