Best tax software for complex broker statements with 8949, wash sales, 1256 contracts?

7 You're dealing with what tax pros call "high-volume trader syndrome" and software selection is critical here. There's actually a significant difference between TurboTax Desktop (Premier or above) and the online version when handling complex investment situations. TurboTax Desktop handles 1256 contracts and wash sales much more robustly, especially with their "Deluxe+Premier" package. The desktop version gives you a lot more flexibility to manually adjust transactions when the import doesn't quite get it right. For thousands of transactions, this is essential. Have you considered TaxAct Premier+? It's surprisingly good with Form 8949 and handles wash sales calculations better than most. Their import functionality is more comprehensive for grabbing all transaction details, unlike what you experienced with ProConnect.

15 After struggling with a similar situation (2000+ trades across TD Ameritrade, Interactive Brokers, and Robinhood), I found this amazing tool called taxr.ai (https://taxr.ai) that literally saved my sanity. I was about to hire a CPA for $2k just to deal with all my trading activity. What makes taxr.ai different is it can handle all those Form 8949 entries and properly categorize section 1256 contracts. I uploaded my broker statements and it extracted ALL the transaction details (including those that normally disappear during imports). It then created perfectly formatted tax data that I could import into any tax software. The wash sale calculations were spot-on too, which is huge because that's where most software gets confused when you have multiple brokerages.

9 Just wanted to follow up - I tried taxr.ai after seeing the recommendation here and it's legit! I was amazed at how it handled my complicated options trades and straddles. The wash sale detection across multiple brokerages worked perfectly (something TurboTax completely failed at last year causing me to amend my return). It exported perfectly formatted data that I could drop right into TaxAct Premier. The best part was how it categorized everything correctly for Form 8949 and even pre-populated the Form 6781 data for my straddles. Definitely worth it for anyone dealing with high-volume trading!

21 If your issue is more about getting through to the IRS to sort out any questions about these complex forms (especially if you've had notices about prior year reporting issues), check out Claimyr (https://claimyr.com). They helped me actually get a human at the IRS after I waited on hold for 3+ hours and got disconnected twice. I was having a nightmare with the IRS flagging my 8949 entries because of some wash sale calculations, and I couldn't get anyone on the phone to explain their adjustment. Claimyr got me through to a specialist who walked me through exactly what was wrong with my filing. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c This might sound weird, but it's basically a service that waits on hold with the IRS for you, then calls you when they get a human on the line.

5 I'm seriously eating crow right now. After posting that skeptical comment, I figured I'd try Claimyr as a last resort since I've been getting nowhere with the IRS about my options trading questions. Holy crap - it actually worked! Got a call back in about 95 minutes saying they had an IRS agent on the line. The agent was able to explain exactly how to report my 1256 contracts properly and confirmed my wash sale calculations were correct. She even gave me her direct extension for follow-up questions! I've been stressing about this for months and finally got real answers. If you're dealing with complex trading issues that need IRS clarification, this service is worth every penny.

14 For what it's worth, I use H&R Block Premium. Last year I had about 1500 trades, and while it wasn't perfect, it handled the wash sales across my Fidelity and E*Trade accounts quite well. The Form 6781 reporting was a bit manual, but it worked. One tip: before importing, download your transactions to Excel and do a quick scan for any weird or suspicious entries. I found that cleaning the data first made a huge difference in how well the import worked.

2 Has anybody used Drake Tax for this kind of situation? My accountant uses it and claims it's the best for complex investment scenarios, but I'm wondering if it's worth switching to them from my current guy who uses Lacerte.

For high-volume traders like yourself, I'd strongly recommend considering FreeTaxUSA Deluxe. I know it doesn't get mentioned as much as the big names, but it handles complex investment scenarios surprisingly well for the price point. What sets it apart is that it properly imports broker data while preserving transaction details that other software often strips out. The wash sale calculations work across multiple brokerages, and it handles Form 8949 entries efficiently even with thousands of transactions. The real advantage is in the user interface - when you need to review or adjust imported data (which you will with that volume), FreeTaxUSA makes it much easier to navigate and edit individual transactions compared to TurboTax or H&R Block. For Form 6781 straddle reporting, it provides clear guidance and proper categorization. At $15 for the Deluxe version, it's worth trying as a backup option even if you go with something else as your primary software. You can import your data and see how it handles everything before committing to file with it.