How to properly report capital gains/losses with hundreds of trades: Schedule D vs. Form 8949 vs. Form 1099-B

Thanks for the clear explanation! I'm using TurboTax Premier. Do you know if it can handle the summary method for the regular trades while still letting me individually list the wash sales? I tried importing my 1099-B, but it's flagging a bunch of issues I need to manually review, and I wasn't sure if I was supposed to be fixing each one or if there's a better way. Also, if I do have to list all the wash sales individually, do I need to include every detail about each trade, or just the adjusted basis amount?

TurboTax Premier should definitely handle this situation. When you import your 1099-B, it will identify the wash sales automatically. You'll need to review the flagged issues, but TurboTax will guide you through correcting them. The software will properly separate regular trades from wash sales and generate the appropriate forms. For wash sales, you do need to include all the transaction details - date acquired, date sold, proceeds, cost basis, and the adjustment amount. TurboTax will fill in these fields once you correct any import issues. The tax code requires complete information for wash sales because these adjustments affect your basis and holding period.

Does it work if you have multiple brokers? I trade through both Fidelity and Robinhood and consolidating everything is a nightmare. Also, how does it handle crypto trades vs stock trades? My tax situation is a mess this year.

I'm skeptical. My brokerage already provides a 1099-B with all my trades. Why would I need another service to process the same info? Does it actually save time compared to just importing directly into tax software?

It works great with multiple brokers. I used it with statements from Schwab and TD Ameritrade, and it consolidated everything perfectly. You just upload all your documents, and it organizes them by broker while ensuring nothing gets double-counted. It's especially helpful for finding wash sales that happen across different platforms, which brokers won't catch themselves. For crypto vs stocks, it handles both but categorizes them correctly. Crypto gets reported differently than securities, and the system applies the right tax rules to each type. It saved me from making several costly mistakes where I would have reported certain crypto transactions incorrectly.

Wait, so this service just calls the IRS for you? How does that even work? Couldn't I just keep calling myself until I get through? I have questions about how my broker reported some of my trades that might be wash sales but aren't marked as such.

This sounds too good to be true. I've tried calling the IRS multiple times and always gave up after 1-2 hours on hold. What's to stop them from just taking your money and not actually connecting you? And even if you do get through, are the IRS agents actually helpful with complex tax questions?

The service doesn't just call for you - it uses technology to stay in the hold queue so you don't have to. It monitors the IRS phone lines and only calls you when an actual agent is about to pick up. You could keep calling yourself, but you'd waste hours on hold each time, especially during tax season when wait times are 2+ hours. IRS agents can be incredibly helpful with reporting questions. While they won't give investment advice, they can clarify exactly how certain transactions should be reported. In my case, they explained precisely how to document wash sales that occurred across different accounts, which even my CPA wasn't 100% sure about. They can also provide guidance specific to your situation that you won't find in general IRS publications.

TaxAct handled my trades pretty well. It automatically flagged the wash sales and let me review just those while summarizing the rest. Much more efficient than when I tried using TurboTax the year before. Plus it was cheaper. Their deluxe version includes all the investment forms.

Thanks for sharing your experience with TaxAct. I might give it a try this year since H&R Block's process was so tedious. Did TaxAct let you import directly from your brokerage, or did you have to manually enter the information? I'm also curious if it handled any foreign investments correctly. I have a few Canadian stocks that always seem to cause issues with the reporting.

There's no maximum page limit for Form 8949. You can attach as many continuation sheets as needed to report all your transactions. Just make sure to number each page and include your name and social security number on each continuation sheet. I had over 200 pages one year and it processed fine. Just make sure you're transferring the totals correctly to Schedule D.

This is incredibly helpful, thank you! The Excel organization approach makes a lot of sense. I'm curious about the basis adjustments you mentioned - when a wash sale gets disallowed, does the software automatically add that loss amount to the basis of the replacement shares, or do I need to manually track and adjust that myself? I'm worried about missing these adjustments and either overpaying or underpaying my taxes. Also, what happens if I have wash sales that carry into 2023 - do those adjustments affect this year's filing or next year's?

Good tax software like TurboTax Premier should automatically handle the basis adjustments for wash sales, but you absolutely need to verify the calculations. The software will add the disallowed loss to the cost basis of the replacement shares, but sometimes it misses wash sales that occur across different accounts or different securities (like selling ABC stock at a loss and buying ABC call options within 30 days). For wash sales that carry into 2023 - if you sold the replacement shares in 2023, then yes, those basis adjustments will affect next year's filing when you report the sale of those replacement shares. If you're still holding the replacement shares, the adjusted basis just sits there waiting until you eventually sell them. I'd recommend creating a simple spreadsheet to track each wash sale: original sale date, loss amount disallowed, replacement purchase date, and new adjusted basis. This way you can double-check the software's work and have documentation if the IRS asks questions later. With hundreds of trades, even small errors in basis adjustments can add up to significant tax differences.