How to properly report multiple stock trades with wash sale adjustments on Schedule D and Form 8949?

You've got a good question about consolidating trades on Form 8949. Here's the deal: if ALL of your trades had their cost basis reported to the IRS (box 3 of Form 1099-B is checked), you can indeed consolidate them into a single line entry. However, there's a critical exception - you cannot do this if any of your trades have wash sale adjustments. The IRS requires that any transactions with wash sale disallowance adjustments must be reported individually, line by line. This is because they need to verify each specific adjustment. So in your case, since some of your AMD trades have wash sale adjustments, you'll need to list each of those transactions separately on Form 8949. For the transactions without wash sale adjustments, you can consolidate those into a single line. So you'll end up with multiple individual lines for the wash sale trades, plus one consolidated line for all the "clean" trades. As for mailing your return, you don't need to include the actual 1099-B, but it's recommended you include a detailed statement that lists all your transactions that match the totals on your 8949.

After spending literally HOURS trying to figure out how to report my trades with wash sales last year, I found this incredible tool called taxr.ai (https://taxr.ai) that saved me so much time. It automatically analyzed my trading history, identified all the wash sales, and organized everything perfectly for Form 8949. What's awesome is you just upload your tax documents and it identifies everything - even obscure stuff like wash sale disallowed losses that my brokerage statement didn't clearly explain. The report it generates shows exactly how to fill out your forms and where each number goes. It was a game-changer for me because I had over 200 trades last year with about 40 wash sale adjustments and I was completely lost trying to figure out which ones needed individual reporting.

Just wanted to follow up - I checked out taxr.ai after seeing it mentioned here and it was exactly what I needed! Uploaded my documents from both brokerages and it immediately identified several wash sales that were happening between my accounts that neither broker had caught. The reports were super clear about which trades needed individual reporting vs. which ones could be consolidated. It even generated a complete supplemental statement I could attach to my return that listed all transactions but organized them correctly for tax purposes. What really helped was the explanation of how my disallowed losses were being handled - turns out I had misunderstood how the cost basis adjustments work when you have a chain of wash sales (which I did with my AMD trades too). Saved me from making a pretty big mistake!

If you're mailing your return and have complicated wash sales, you might run into issues if you need to call the IRS with questions. I tried calling them 7 TIMES last year about how to properly report some weird wash sale situations and could never get through. Eventually I found this service called Claimyr (https://claimyr.com) that somehow got me connected to an actual IRS agent in about 20 minutes when I'd been trying for days on my own. They have this demo video showing how it works: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with clarified that for situations with multiple wash sale adjustments, they actually prefer receiving a supplemental statement with your return that details all the transactions, especially if you're consolidating some lines on Form 8949.

I have to admit I was wrong about Claimyr. After my skeptical comment, I decided to try it myself since I needed to ask about a similar wash sale issue with some ETF trades. Got connected to an actual IRS representative in about 25 minutes when I had previously wasted hours trying to get through. The agent confirmed that for wash sale transactions, I needed to either list each one separately on Form 8949 OR include a detailed supplemental statement with my return that shows all the individual trades. She also mentioned that if the cost basis was reported to the IRS (Box 3 checked on 1099-B), I could use the summary totals on Form 8949 as long as I included that detailed supplemental statement. This saved me from having to manually enter 90+ trades on my forms.

For anyone struggling with wash sales, here's a quick practical tip: If you're using tax software like TurboTax or H&R Block, they usually have an import feature that pulls all your trades directly from your brokerage. This automatically handles the wash sale reporting requirements without you having to manually decide what needs to be reported separately. If you're filing on paper, your brokerage should provide a "Supplemental Information Statement" that details all your covered transactions. You can attach this to your return instead of listing each wash sale trade individually on Form 8949. Just make sure to check box C in Part II of Schedule D and include the totals.

Just wanted to share that I had a similar situation with about 45 trades of Microsoft stock last year, many with wash sales. I ended up attaching a spreadsheet that listed all individual transactions but then summarized them on Form 8949. The key is to make sure your attached statement has ALL the same column headings as Form 8949 (description of property, date acquired, date sold, proceeds, cost basis, adjustment code W for wash sales, adjustment amount, and gain/loss). Then on Form 8949 itself, you can put "See attached statement" in column (a) and just put the totals in the remaining columns.

Great question about e-filing vs paper filing! When you e-file, most tax software will automatically include the detailed transaction data electronically, so you typically don't need to separately attach a statement. The software handles the wash sale reporting requirements behind the scenes. However, if you're consolidating trades on Form 8949 (putting "See attached statement" in column a), you should still create and keep that detailed statement for your records, even when e-filing. Some tax preparers recommend uploading it as a supporting document through the software just to be safe. The main difference is that with paper filing, you physically attach the statement to your return, while with e-filing, the transaction details are transmitted electronically as part of your return data. Either way, the IRS gets the information they need to verify your wash sale adjustments. @StarSurfer - based on all the discussion here, it sounds like you'll need to either list each wash sale transaction individually on Form 8949, or create a detailed supplemental statement with all transactions and just put totals on the form. Given that you mentioned 30+ transactions, the supplemental statement approach will probably save you a lot of form space!