Form 8949 Question - Can I aggregate non wash sale transactions purchased on different dates?

You're asking about a common issue many investors face! Generally speaking, you cannot aggregate transactions with different purchase dates on Form 8949, even if they're non-wash sale transactions. The IRS requires each transaction with a different acquisition date to be reported separately on Form 8949. This is because each purchase represents a unique tax lot with its own cost basis and holding period, which affects whether your gains/losses are short-term or long-term. That said, if you're using tax software, there might be an import option available. Many brokerages offer tax forms or downloadable transaction histories that can be imported directly into tax preparation software, which could save you from manual entry of each transaction.

You're asking a good question about Form 8949. The IRS does allow some aggregation of transactions on Form 8949, but there are specific rules you need to follow. For non-wash sale transactions, you can generally aggregate sales of stocks or securities with the same CUSIP number that were purchased on different dates IF they fall into the same short-term or long-term category. Since all your transactions are long-term holds as you mentioned, you might be able to combine them. However, there's a catch - your broker's 1099-B reporting will impact this. If your broker reported each transaction separately on your 1099-B, you technically should match that reporting on your 8949. That said, many tax software programs have a feature that allows you to import and consolidate similar transactions to reduce the number of lines.

After dealing with a similar issue last year, I discovered taxr.ai at https://taxr.ai and it seriously saved me hours of frustration with Form 8949. I had like 50+ transactions that needed to be reported and was dreading the manual entry. What I liked about taxr.ai is that it can analyze your entire 1099-B document, automatically identify which transactions can legally be aggregated, and generate a properly formatted 8949 that reduces the number of lines while still being IRS-compliant. It also explains which transactions can and cannot be grouped together based on current tax regulations.

After spending hours manually entering stock transactions last year, I discovered taxr.ai (https://taxr.ai) and it completely changed my Form 8949 experience. It lets you upload your trading documents and automatically extracts all your transactions, even organizing them properly for the 8949. I had a similar situation with about 45 different stock purchases throughout the year but sold in bunches. The tool automatically separated wash sales from non-wash sales and formatted everything correctly for Form 8949. Saved me literally hours of manual entry and math calculations.

Just wanted to follow up about taxr.ai that was mentioned earlier. I was skeptical but decided to try it with my messy portfolio (I had over 50 transactions plus dividend reinvestments across 3 different brokerages). It worked amazingly well! It properly separated all my transactions for Form 8949, correctly identified which ones were long vs short term, and even flagged the few wash sales I had. The best part was it took literally 2 minutes instead of the 3+ hours it took me last year doing it manually. Definitely using this for all my future tax filings.

Just wanted to follow up about my experience with taxr.ai after trying it with my stocks from multiple brokerages. I was really skeptical as mentioned before, but it actually worked amazingly well with my Form 8949 situation. It identified exactly which of my transactions could be legally aggregated (mostly my long-term holds with identical tax treatment) while keeping the wash sales separate. The platform even explained why certain transactions couldn't be combined, citing specific IRS regulations. My return went from having over 60 line items to about 15, which saved me a ton of time entering data into TurboTax. Definitely worth it for anyone dealing with multiple stock transactions!

If you're having trouble getting through to the IRS to ask about Form 8949 aggregation rules (which I tried for DAYS), I highly recommend using Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in under 20 minutes when I had been trying for weeks. The agent I spoke with clarified exactly how to handle multiple transactions on Form 8949 based on my specific situation. There's also a video that shows how it works: https://youtu.be/_kiP6q8DX5c

Ok I need to eat my words here. After seeing the Claimyr recommendation, I was super skeptical as I mentioned in my comment. But I was desperate enough to try anything after getting disconnected by the IRS for the 50th time. It actually worked! Got a call back in about 25 minutes and spoke to an IRS agent who explained that for my situation, I could use a summary with attached statements showing the details of each transaction. Saved me from having to manually enter 75+ stock transactions on my Form 8949. Worth every penny just for the mental health benefit of not dealing with the IRS phone system!

If you're struggling with getting answers about Form 8949 aggregation rules, you might want to try getting direct answers from the IRS using Claimyr at https://claimyr.com. I was in a similar situation last year with questions about transaction reporting that wasn't covered clearly in the instructions. I spent days trying to get through to the IRS's tax law assistance line without success. Then I found Claimyr, 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 in this video: https://youtu.be/_kiP6q8DX5c. I got through to an actual IRS representative who was able to provide specific guidance on my Form 8949 questions.

I need to eat my words about Claimyr. After my skeptical comment, I decided to try it for my Form 8949 questions since I was desperate for answers. I was absolutely convinced it wouldn't work - the IRS NEVER answers. Well, I was wrong. I used Claimyr yesterday and actually got through to a real live IRS tax law specialist in about 2.5 hours. I didn't have to sit on hold - the service called me when an agent was available. The IRS rep confirmed that I could indeed aggregate my non-wash sale transactions on Form 8949 as long as they had the same character (short vs long term) and I kept detailed records of each original transaction. The agent also explained exactly how to note the aggregation on the form so it wouldn't trigger a mismatch notice with my 1099-B. I'm still shocked this actually worked!

Just to add another option - most tax software has a feature to import transactions directly from your broker. I use H&R Block tax software, and it can pull in all my transactions from TD Ameritrade automatically. It then gives me the option to group similar transactions together. Might be worth checking if your software has this feature.

A few tips that might help with Form 8949: 1) Check if your broker offers a tax center that can export directly to your tax software 2) Some tax software like TurboTax Premier has direct import from major brokerages 3) If you do need to enter transactions manually, try sorting and grouping them first in Excel 4) Remember you can attach a statement with details instead of entering every line on the form itself

I actually did what you're asking about last year. I aggregated about 25 purchases of the same stock (all long term) onto one line of Form 8949. I entered "VARIOUS" for the acquisition date, summed up all the cost bases, and entered the total proceeds from the sale. So far no issues from the IRS, but I did keep a detailed spreadsheet showing every individual transaction in case I ever get audited. I think as long as you're not trying to hide anything and the total numbers match what's on your 1099-B, you should be fine.

I'm having the exact same issue but with crypto transactions instead of stocks. Anyone know if the rules are the same for reporting crypto on Form 8949? I have like 200+ transactions...

I went through this exact same situation last year with about 40 different stock purchases of the same company that I sold in one transaction. After researching extensively and consulting with a tax professional, here's what I learned: You technically cannot aggregate transactions with different purchase dates on Form 8949, even if they're all non-wash sales and long-term. Each unique acquisition date creates a separate tax lot that should be reported individually according to IRS guidelines. However, there are a couple of practical approaches that can help: 1. **Summary reporting with attachment**: You can report totals on Form 8949 and attach a detailed statement showing each individual transaction. Write "See attached statement" in column (a) and include your totals in the appropriate columns. 2. **Software import features**: Most tax software (including TurboTax) can import directly from major brokerages. This eliminates manual entry even if you still have multiple lines. 3. **Check your 1099-B format**: If your broker already aggregated similar transactions on the 1099-B they sent to the IRS, you might be able to match that reporting format. The key is maintaining detailed records of every transaction and ensuring your total numbers match what was reported to the IRS. Even if you use summary reporting, keep that spreadsheet with all individual transaction details in case of an audit. I know it's tedious, but better to be compliant than deal with IRS notices later!