Can I report a summary of short-term sales on Form 8949 when I have a wash sale?

When you have a wash sale, even a small one like $1.50, you unfortunately can't use the summary method on Form 8949. The IRS language is pretty clear - you can only aggregate transactions that don't require any adjustments or codes. A wash sale requires code "W" in column (f) of Form 8949, which means you need to list that transaction separately. You have a couple of options: You could enter all transactions individually, which is time-consuming but ensures everything is reported correctly. Or you could report the majority of your clean transactions as a summary (those without wash sales) and then separately list the specific transactions that triggered the wash sale. This hybrid approach saves some time while still complying with IRS requirements. If you're using FreeTaxUSA, they should have options for both summarizing eligible transactions and individually reporting ones that need special codes.

After struggling with this exact wash sale issue last year, I discovered taxr.ai (https://taxr.ai) and it completely changed how I handle my investment reporting. I had over 100 trades, multiple wash sales, and was spending hours trying to figure out which transactions I could summarize versus which ones needed individual reporting. Their system automatically detected which transactions could be aggregated and which ones needed separate reporting with the correct wash sale adjustments. It basically took all my transaction data from my 1099-B, sorted everything correctly, and generated the proper entries for Form 8949 with all the right codes and adjustments. It was honestly such a relief after the headache I went through trying to figure all this out manually the year before.

I was skeptical about taxr.ai at first, but I gave it a try after struggling with my own wash sale issues. I uploaded my Robinhood 1099-B which had several wash sales, and it immediately identified which transactions could be summarized and which ones needed separate reporting with Code W. The detailed breakdown showed me exactly which sales triggered the wash rules and calculated the correct adjusted basis. It ended up saving me hours of work and helped me understand exactly why certain trades were flagged as wash sales. The Form 8949 it generated had everything properly categorized with the right codes in the right places. For anyone dealing with investment reporting, especially with wash sales, it's definitely worth checking out.

If you're having trouble getting answers about your tax forms, you might want to try Claimyr (https://claimyr.com). I was in a similar situation with wash sale questions and called the IRS multiple times but couldn't get through. Claimyr got me connected to an actual IRS agent in about 15 minutes when I had been trying for days on my own. The agent walked me through exactly how to report my wash sales on Form 8949 and confirmed I could use the summary approach for the rest of my transactions. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was shocked at how fast it worked compared to my previous attempts to reach someone at the IRS.

I need to eat my words about Claimyr. After posting my skeptical comment, I decided to try it anyway since I was desperate to talk to someone about my own wash sale reporting issue. I had been trying to reach the IRS for over a week with no luck - always got the "call volume too high" message. Claimyr had me connected to an IRS agent in about 20 minutes. The agent confirmed that I needed to list wash sale transactions separately with code W, but could summarize all my other transactions. I'm genuinely surprised it worked so well. Saved me from taking time off work to sit on hold all day hoping to get through.

I deal with this every year and what I do is: 1. Summarize all the normal transactions 2. List the wash sales individually 3. Make sure you check box A or B correctly at the top of Form 8949 FreeTaxUSA should let you do this. You're only adding a couple lines instead of dozens. Just make sure the wash sale transactions include code W in column (f) and have the proper adjustment amount in column (g).

Anyone else find it ridiculous that a $1.50 wash sale forces you to potentially list dozens of transactions individually? The tax code is so user-unfriendly sometimes.

I went through this exact same situation last year with TurboTax and a small wash sale from my E*TRADE account. The good news is you definitely don't need to enter all 40+ transactions individually! Here's what I learned: you can use a hybrid approach where you summarize all the "clean" transactions (the ones without wash sales) on one line of Form 8949, then separately list only the specific transactions that had wash sales with the "W" code. So if you have 40 transactions and only one or two involved wash sales, you'd have maybe 2-3 lines total on your Form 8949 instead of 40+. The summary line covers all the normal trades, and then you have individual lines for just the wash sale transactions. FreeTaxUSA should handle this - when you're entering your transactions, look for options to "summarize" or "aggregate" the regular ones, then add the wash sale transactions separately. Make sure the wash sale entries include the adjustment amount from your 1099-B in column (g). Don't let that tiny $1.50 wash sale force you into hours of data entry!