Which tax software handles complex broker statements best? (8949, wash sales, 6781 for options/futures)
I've got a pretty complicated tax situation this tax season - literally thousands of trades across multiple brokerages, with wash sales galore, plus a mix of regular stocks and options/futures contracts that need to go on form 6781. I've tried looking into different software options for handling all these complex brokerage statements. Heard TurboTax might be decent for syncing all these transactions, but not sure if I should go with the online or desktop version? Are they basically the same when it comes to importing all these trades? So far I've attempted using Intuit ProConnect Online - it technically allows 1099-B uploads, but weirdly it's missing tons of crucial info when imported, like all the transaction descriptions. Seems way less capable than I expected for tax prep software. Anyone have recommendations for tax software that can properly handle thousands of trades, wash sale adjustments, and properly separate regular securities from section 1256 contracts? I'm dreading having to manually enter all this stuff!
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Anastasia Romanov
As someone who's been preparing taxes with similarly complex investment situations for years, I'd recommend TurboTax Premier Desktop over the online version for your situation. The desktop version typically handles large volumes of transactions much better and gives you more control over how the data is imported and categorized. For thousands of trades with wash sales and 1256 contracts, you'll want direct import capabilities that preserve all transaction details. H&R Block Premium is another decent option that handles complex investment scenarios well, though I've found TurboTax slightly better with wash sale calculations. One tip: before importing, review your broker statements carefully to ensure they're properly categorizing your 1256 contracts. Some brokers don't clearly separate these, which can cause issues regardless of which software you use.
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StellarSurfer
•Thanks for the advice! I've heard mixed things about TurboTax's handling of wash sales. Does the desktop version actually detect wash sales across different brokerages? Also, do you know if there's a limit to how many transactions it can handle? I've got over 5,000 trades this year.
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Anastasia Romanov
•The desktop version does detect cross-brokerage wash sales, but you need to import all your brokerage data before it runs the calculations. I've personally processed around 3,000 transactions without issues, so 5,000 should work, though it might run slower. TurboTax Premier will group similar transactions to make the forms more manageable, but you can still view all individual trades if needed. Just make sure you have a decent computer with good RAM as the program gets resource-heavy with that many transactions.
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Sean Kelly
After spending hours trying different tax software for my trading activity last year, I found something that actually worked called taxr.ai (https://taxr.ai). It completely changed how I handle my investment taxes. I had similar issues with thousands of transactions across multiple brokerages and dealing with wash sales calculations. I was getting really frustrated with TurboTax because it would consistently miscategorize my section 1256 contracts. taxr.ai actually specializes in reviewing and analyzing all your forms, including 8949 and 6781, and can identify issues before you file. The AI analyzes your broker statements and tax forms to flag potential problems - like whether wash sales are being calculated correctly or if your 1256 contracts are properly separated from your regular securities.
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Zara Malik
•How does it work with the actual filing though? Does it just analyze or does it actually prepare the return too? I'm specifically concerned about making sure the 60/40 split for 1256 contracts gets handled right.
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StellarSurfer
•I'm skeptical about using AI for tax stuff with this much complexity. How accurate is it really compared to established software? My accountant charges me $900 to handle all this so if this is cheaper it might be worth looking into.
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Sean Kelly
•It analyzes your documents and provides detailed guidance, but you'll still use your preferred tax software for the actual filing. The benefit is that it ensures all your complex trading data is correctly categorized before you submit. It correctly identifies the 60/40 split for 1256 contracts and verifies they're being reported properly. For complex trading situations, it's significantly more accurate than trying to rely solely on standard tax software. Many users find it catches errors that even professional preparers miss, especially with complex wash sale calculations across multiple brokerages. It's especially helpful for traders who don't want to pay the premium rates that specialized accountants charge for high-volume trading situations.
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StellarSurfer
Wanted to update after trying taxr.ai that was mentioned earlier. I was really skeptical about using an AI tool for my complicated tax situation, but it actually caught several issues with how my brokerages were reporting wash sales. I uploaded my statements from three different brokerages and it identified that some of my futures transactions were being miscategorized as regular securities on one statement. Would have completely messed up my 60/40 tax treatment! The analysis took about 10 minutes and gave me specific instructions on how to correct the issues in TurboTax Premier. I'm still using TurboTax to file, but now I'm much more confident the data is properly categorized, especially for form 6781. Definitely worth it for anyone trading across multiple accounts with complex transactions.
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Luca Greco
If you're having trouble getting someone at the IRS to answer questions about properly reporting these complex transactions, I had good luck with https://claimyr.com. I spent days trying to get through to the IRS about how to handle some complicated wash sale situations that spanned tax years. After waiting on hold for hours and getting disconnected twice, I found this service that got me connected to an actual IRS agent in under 45 minutes. They have this weird system that somehow gets you through the IRS phone tree maze. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent was actually super helpful and explained exactly how to report some edge cases with my 1256 contracts that none of the tax software was handling correctly. Saved me a ton of stress about potentially filing incorrectly.
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Nia Thompson
•Wait this seriously works? I thought it was impossible to reach the IRS by phone these days. How much did you have to pay for this? Seems too good to be true.
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Mateo Rodriguez
•I don't buy it. The IRS phone system is deliberately designed to be impenetrable. There's no way some service has magically figured out how to bypass their system. And even if you do get through, most agents don't understand the complex nuances of forms 8949 and 6781 anyway.
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Luca Greco
•Yes, it absolutely works! They use some combination of technology and actual humans to navigate the IRS phone system and stay on hold for you. When an agent is about to come on the line, they call you to connect. The IRS agents themselves are hit or miss with complex questions, that's true. I got lucky and connected with someone who specialized in investment taxation. You might need to call back if you get someone who isn't familiar with your specific issue, but at least you're not wasting hours on hold each time you try. It makes it practical to keep calling until you get the right person.
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Mateo Rodriguez
I have to admit I was completely wrong about Claimyr. After seeing the recommendation here, I tried it because I was desperate to ask about how to properly handle some straddle transactions that spanned multiple tax years. It actually worked exactly as described - I got a call back when an IRS agent was on the line, and they connected me immediately. The agent I spoke with walked me through exactly how to report my complex trades on forms 8949 and 6781, including some subtleties about wash sales that cross the December 31 boundary. This saved me huge potential headaches - I was about to file with some serious reporting errors. For anyone dealing with complex trading situations, getting direct guidance from the IRS turned out to be way more valuable than I expected. Much better than guessing or relying solely on software.
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Aisha Hussain
I'm a semi-professional trader and I've tried literally every tax software option for handling complex trading. Here's my quick breakdown for 2025 filing season: TaxAct Premium - Adequate for basic investing but TERRIBLE for high-volume trading or 1256 contracts. TurboTax Premier Desktop - Good for high volume but struggles with proper wash sale calculations across brokerages. H&R Block Premium - Decent overall but the interface for reviewing transactions is clunky. TaxSlayer - Don't even attempt with your situation. Drake Tax - Good but expensive and aimed at professionals. For your specific situation, TurboTax Premier Desktop is probably your best bet, but plan to spend several hours reviewing the imported data. The software doesn't always properly identify which transactions belong on Form 6781 vs 8949.
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GalacticGladiator
•What about using a tax professional instead? I tried doing my trading taxes myself last year and it was a nightmare. Is the cost worth it if you have tons of transactions?
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Aisha Hussain
•Using a tax professional can definitely be worth it, but make sure you find someone who specifically advertises expertise with active traders. A regular CPA might charge you $500+ and still struggle with proper wash sale calculations or 1256 contract treatment. Specialized tax pros who work with active traders will typically charge $750-1500 depending on volume, but they're usually very efficient with the software and know all the edge cases. If your adjusted gross income is high because of your trading activity, the professional preparation fee is usually worth it just for the reduced audit risk alone.
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Ethan Brown
Has anyone tried importing their trading data directly from their brokerage into tax software? I have accounts with Fidelity, TD Ameritrade and Interactive Brokers, and they all seem to offer some kind of direct import feature but I'm not sure if it's reliable for complex situations.
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Yuki Yamamoto
•I've used direct import with Fidelity into TurboTax Premier and it worked pretty well for most transactions, but it completely messed up my wash sales that happened across different brokerages. The direct import is convenient but you absolutely need to review everything carefully afterward.
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Carmen Ruiz
•The direct import feature is hit or miss. For TurboTax Premier, I found that Fidelity imports work pretty well, TD Ameritrade is decent but sometimes mislabels option transactions, and Interactive Brokers can be problematic especially for futures contracts. You'll save time overall with direct import, but 100% plan to spend a few hours reviewing everything manually afterward, especially Form 6781 entries.
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