TurboTax marked box F instead of box E on form 8949 for my 1099-b transactions. How serious is this mistake?

Thanks for the explanation! But I'm still confused about one thing - if the IRS gets my 1099-B directly from my broker, won't they notice the discrepancy with the wrong box checked? Could this trigger some kind of matching issue in their system?

The IRS does receive your 1099-B information directly from your broker, but their matching system is primarily focused on the dollar amounts rather than which box is checked. Their main concern is whether you've reported all your sales proceeds. The box selection is more of an organizational element that helps with the preparation of the form. Since you've included all the correct transaction details and amounts, the likelihood of this triggering any issues is very low. The IRS reconciles the total proceeds reported, and as long as those match and you've calculated your gains correctly, you should be fine without an amendment.

Does taxr.ai actually check for form-specific errors like this? I have a similar situation but with a K-1 form where I think my tax preparer coded something wrong. Would it catch that kind of mistake too?

I'm a bit skeptical about these tax AI tools. How accurate is it really? Does it actually understand all the nuances of tax law or is it just making general recommendations? Just wondering if it's worth trying.

Yes, it definitely checks for form-specific errors! That's actually one of its strengths - it understands the relationships between different tax forms and can spot inconsistencies. It would definitely help with K-1 coding issues, as those are actually more significant than the box checking on 8949 in many cases. For your question about accuracy - I was skeptical too at first, but it's built on actual tax regulations and is constantly updated. It doesn't just make general recommendations - it provides specific citations to IRS publications and explains the reasoning behind its analysis. It's not just guessing or using general rules of thumb like a lot of advice you get online.

Wait, how does this actually work? The IRS phones are notoriously impossible to get through on. Are you saying this service somehow jumps the queue or something?

Sorry, but this sounds like BS to me. I highly doubt any service can magically get you through to the IRS faster. They're probably just keeping you on hold themselves and charging you for it. Has anyone else actually had success with this?

It doesn't jump the queue at all. What it does is use an automated system to wait in the IRS phone queue for you. Basically, it calls the IRS, navigates the menu options, and then waits on hold while you go about your day. When it detects that an agent is about to come on the line, it calls your phone and connects you directly to the IRS agent. No, they're definitely not keeping you on hold themselves - I was connected directly to an IRS agent who verified she worked for the IRS and answered my tax questions in detail. I was skeptical too until I tried it. The whole point is that you don't have to waste hours listening to the IRS hold music. I ended up waiting about 2.5 hours for my callback, but I was able to do other things instead of being stuck on the phone.

So would you recommend just leaving it as is? I'm in the same boat with H&R Block this year and trying to decide if it's worth the hassle of amending.

Based on my experience, I would leave it as is if all your actual numbers are correct. The amendment process is a hassle and can actually increase your chances of getting additional scrutiny. The IRS matching program primarily focuses on the dollar amounts reported, not which classification box is checked. If you correctly reported all your sales proceeds, cost basis, and calculated the proper gain/loss, that's what truly matters. I've gone through two tax seasons since my form had the wrong box checked, and it's never been an issue.

Which tax software do you find makes the fewest mistakes with these technical form details? I've tried several and they all seem to have these kinds of issues.

In my experience, TaxAct has been the most accurate with technical form details, especially for investment-related forms like 8949. It doesn't make as many assumptions as TurboTax or H&R Block, which forces you to be more deliberate about your choices. FreeTaxUSA is also surprisingly good with these details despite being less expensive. The interface isn't as polished, but it tends to ask more specific questions about form selections rather than making default choices. The downside is you have to be more knowledgeable about what the forms are asking, but the benefit is fewer automatic errors like the box E vs F situation.

This is really reassuring to hear from someone who went through the exact same situation! I'm definitely leaning towards not amending now. You make a great point about amendments potentially drawing more scrutiny - I hadn't thought about that aspect. Since you've had two years with no issues, that gives me a lot more confidence that this box error isn't worth the hassle of fixing. Thanks for sharing your experience!