How to Summarize Multiple Wash Sales on Schedule D and Form 8949

Thanks for the response. My brokerage (Fidelity) does provide adjusted basis for covered securities, but not for the RSUs since they're non-covered. And the problem is that the wash sales chain between both types of securities, so I don't think I can rely on their reporting for even the covered portion. Is there any IRS guidance specifically about summarizing wash sales when they get this complex? I'm worried about an audit if the numbers don't precisely match what the brokerage reports to the IRS.

You're right to be cautious about the interaction between covered and non-covered securities. When wash sales chain between the two types, it creates a situation where the broker's reporting is incomplete. The IRS doesn't provide specific guidance for summarizing complex wash sale situations like yours. The safest approach is to report each transaction with its appropriate adjustments. However, if you're confident in your calculations and all positions are closed, you could consider reporting summary lines for each type (covered vs. non-covered) with a statement attached to your return explaining the wash sale calculations in detail. If you choose to summarize, make sure your total gain/loss equals what it would be if reported individually. Keep detailed workpapers showing how you arrived at your numbers in case of questions from the IRS. The key requirement is that your final reporting accurately reflects all appropriate basis adjustments from the wash sales.

Does it work if I've already sold everything? My concern is that I've got so many transactions across different months, and I'm not even sure I have all the confirmation slips anymore.

I'm skeptical about this. How does it handle the distinction between covered and non-covered securities? My broker (E*Trade) doesn't even provide the correct basis for my RSUs because of how they calculate the tax withholding at vest.

Yes, it actually works better if you've already sold everything since the complete chain of wash sales can be identified. You don't need individual confirmation slips - it can work with your brokerage statements or transaction history exports. As long as you have the complete list of buys and sells for the year with dates, prices and quantities, it can reconstruct the chains. For covered vs non-covered securities, you just identify which transactions fall into each category, and the system handles them separately for Form 8949 purposes. It's specifically designed to handle RSUs where the broker reporting is incomplete. It can also account for the tax withholding calculations at vest, which is one of the trickiest parts with employee stock plans.

How does this actually work? It seems weird that a third-party service could somehow get you to the front of the IRS phone line when millions of people can't get through.

I call BS on this. I've been dealing with IRS issues for years and there's no magic way to jump the phone queue. Even tax professionals have to wait. The IRS barely has enough staff to answer a fraction of calls, so I highly doubt this works as claimed.

It actually uses the IRS's own callback system, but with automated technology to handle the waiting and queuing. You don't "jump the line" - it basically just waits in the phone queue for you and then connects you when an agent becomes available. They explain the technology on their site, but basically it keeps redialing and navigating the IRS phone tree until it succeeds in getting into the callback queue. Once you're in that queue, the IRS system calls you back when it's your turn to speak with an agent. It's completely legitimate and uses the IRS's own systems. I was skeptical too, but when you're trying to get technical tax questions answered about things like wash sale reporting across covered and non-covered securities, sometimes you really need to speak directly with the IRS. This just makes that possible without the frustration of spending days on hold.

I've used TurboTax Premier in the past, but it struggled with the chaining between covered and non-covered securities. Did you have to manually identify the wash sale chains, or did the software somehow figure that out automatically?

The software wasn't able to automatically identify chains between covered and non-covered securities. I had to manually review the transactions and make adjustments where the wash sales crossed between the two types. What worked for me was first importing everything from my brokerage. Then I reviewed each transaction with a loss to see if there were any purchases within the 30-day window before or after. For those that triggered wash sales between different security types, I manually adjusted the basis. It's definitely not perfect, but it saved me from having to create the forms from scratch. The key is understanding which transactions the software might miss so you can focus your manual review efforts there. In my case, I found it helpful to create a simple timeline of all transactions and mark the wash sale periods to visually identify potential issues.

Did your return get accepted without issues? I'm wondering if this triggers any automated flags in the IRS systems since the numbers won't match exactly what the broker reported.

This is exactly what I was hoping to find! My situation is almost identical - I'm looking at around 50+ lines and the complexity is getting overwhelming. A few follow-up questions if you don't mind: 1. How detailed was the explanatory statement? Did it include every single transaction or just the key wash sale chains? 2. When you say the totals matched what would have been reported line-by-line, did you verify this by actually calculating it both ways? 3. Any issues during processing or correspondence from the IRS afterward? I'm really tempted to go this route since manually entering 50+ lines seems like a recipe for errors, and the summarized approach sounds much more manageable while still being compliant.

Great questions! Here are the details from my experience: 1. The explanatory statement was quite comprehensive - it included every transaction with dates, quantities, and prices, plus a clear table showing how each wash sale was calculated and which transactions were involved in each chain. My CPA said the IRS wants to see that you understand the rules and applied them correctly. 2. Yes, we absolutely verified by calculating both ways. I actually started doing it line-by-line first, got overwhelmed, and then my CPA suggested the summary approach. We double-checked that the total gain/loss and basis adjustments were identical between the two methods. 3. No issues at all during processing, and it's been over a year with no correspondence. The key was making sure everything was properly documented and that our summary accurately reflected all the wash sale adjustments. One tip: make sure your explanatory statement clearly identifies which transactions are covered vs. non-covered, and show the wash sale chains separately for each type. This helps demonstrate that you properly handled the distinction that causes so many issues with broker reporting. The peace of mind from having clean, organized forms was worth it, especially since the alternative was 70+ lines with high potential for data entry errors.