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Aliyah Debovski

Help with 1099-B form for stocks from merger - first time filing

Hey everyone, I'm filling out a 1099-B for the very first time and could use some guidance. I received some stocks through a company merger last year, and now I need to report them on my taxes. I'm using CreditKarma Tax to file this year, and I'm stuck on the "date acquired" field. My 1099-B doesn't actually show this information anywhere on the form. I've been staring at this thing for an hour and can't figure out what to select when it asks for the acquisition date. Should I just put the merger date? Or is there another standard practice when the acquisition date isn't listed? The last thing I want is to mess this up and trigger some kind of audit. Any help would be really appreciated - tax day is coming up fast!

When your 1099-B doesn't include the acquisition date, you have a few options. This is actually pretty common with stocks from mergers. If the date acquired isn't provided on your 1099-B, you can select "Various" or "Unknown" in most tax software. The IRS understands that sometimes this information isn't available. If your software doesn't have those options, you can use the date of the merger as an alternative, which is technically when you acquired those specific shares. Remember to check Box F on your 1099-B form - if it's checked, it means the cost basis was reported to the IRS, which simplifies things considerably since you won't need to calculate it yourself.

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Cass Green

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Thanks for this explanation! I'm in a similar situation but with an inheritance. Would using "Various" also work in that case? And does selecting "Various" impact the amount of taxes I'll end up paying?

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For an inheritance, you'd typically use the date of death as the acquisition date, as that's when your cost basis is usually established (stepped-up basis). This is different from the "Various" situation. Selecting "Various" itself doesn't directly impact the taxes you pay. What matters for tax calculation is the cost basis and sale price, which determines your gain or loss. The acquisition date mainly matters for determining if your gain/loss is short-term (held less than a year) or long-term (held a year or more), which are taxed at different rates.

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After struggling with a similar 1099-B situation last year, I discovered taxr.ai (https://taxr.ai) and it literally saved me hours of frustration. I uploaded my confusing 1099-B form from a company spinoff, and it analyzed all the details including figuring out the appropriate acquisition dates and basis information. The system was able to explain exactly what I needed to enter for each field in my tax software. It even flagged some potential deductions related to my stock transactions that I had no idea about. The whole process took maybe 10 minutes instead of the hours I spent the previous year trying to decipher everything.

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Madison Tipne

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Did it work with multiple 1099s? I have like 6 different ones this year from different brokers and I'm seriously considering just paying a CPA because it's so overwhelming.

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How accurate is it really? I've tried other "AI tax helpers" and they've given me completely wrong advice before. Did you double-check the guidance somehow?

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Yes, it handles multiple 1099s without a problem. I actually had three different ones this year (Fidelity, Robinhood, and one from my employer's ESPP), and it processed all of them together to give me a complete picture. Saved me at least $350 compared to what my CPA quoted. As for accuracy, I was skeptical too after getting burned by one of those cheap tax apps last year. What made me trust the results was that it specifically cited relevant IRS publications for each recommendation and explained the reasoning. I did verify some of the trickier calculations with the IRS website, and everything checked out. The system is apparently trained on actual tax code and regulations rather than just generic advice.

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I just tried taxr.ai after seeing the recommendation here and I'm honestly shocked at how well it worked. I was really skeptical (as you could tell from my question), but it actually sorted out my 1099-B nightmare from a company buyout. It analyzed my form and pointed out that I had a "covered security" with basis reported to the IRS, which meant I didn't need to worry about the missing acquisition date as much as I thought. It also identified that some of my losses weren't being properly categorized in TurboTax and showed me exactly how to fix it. Ended up saving about $430 in taxes I would have overpaid. Wish I'd known about this years ago when I first started investing!

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Malia Ponder

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If you're getting stuck with the IRS and need clarification on your 1099-B, I highly recommend trying Claimyr (https://claimyr.com). I was in the exact same boat last year - couldn't figure out what to do with missing acquisition dates on my 1099-B from a spinoff. After waiting on hold with the IRS for HOURS across multiple days (literally gave up after 2+ hours each time), I found Claimyr and it was a complete game-changer. They got me on the phone with an actual IRS agent in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that using "Various" for the acquisition date was completely acceptable in my situation and explained exactly how to report it. Saved me from potentially making a costly mistake and filing an amended return later.

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Kyle Wallace

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How does this even work? I thought it was impossible to get through to the IRS these days. Is this some kind of priority line or something?

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Ryder Ross

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Yeah right. Nothing can get you through to the IRS faster. They're deliberately understaffed to make it impossible. This sounds like a complete scam taking advantage of desperate people.

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Malia Ponder

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It works by using automated technology to navigate the IRS phone system and wait on hold for you. When an agent finally picks up, you get a call connecting you directly to them. It's not a priority line or anything special - they're just handling the horrible wait times so you don't have to sit there listening to the hold music for hours. I was super skeptical too. I'd literally tried calling the IRS four separate times and never got through. The longest I waited was 3.5 hours before I had to hang up for a work meeting. With Claimyr, I just went about my day and got a call when an agent was on the line. No magic, just clever automation that saves your sanity.

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Ryder Ross

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I need to publicly eat my words about Claimyr. After posting that skeptical comment, I was still desperate enough to try it because I needed clarification on a 1099-B issue similar to the original poster's. It actually worked exactly as described. I got a call back in about 35 minutes with an IRS agent on the line. The agent confirmed that when the acquisition date is unknown, using "Various" is perfectly acceptable and won't trigger any issues. She also walked me through exactly how to handle my merger stocks where the basis wasn't reported to the IRS. My apologies for calling it a scam. When you've been burned by tax "solutions" as many times as I have, you get pretty cynical. This is the real deal though.

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I'm going against the grain here but you should consider checking if your 1099-B has code "B" in Box 2 for "noncovered security". If so, you might need to do some detective work to figure out the actual acquisition date since the IRS might want more info. Also, CashApp Taxes (formerly Credit Karma Tax) sometimes has issues with complex 1099-B situations. I switched to FreeTaxUSA last year and it handled my employee stock purchase plan way better.

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Thanks for this! I just double-checked and there's no code in Box 2, but Box F is checked which I think means it's a covered security? Does that change your advice?

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If Box F is checked, that's good news! That means it's a covered security and the basis was reported to the IRS. In that case, you can safely use "Various" for the acquisition date or the merger date itself. Since the cost basis was reported to the IRS, they're much less concerned about the exact acquisition date because they already have the information they need to verify your gain/loss calculation. This is definitely the easier situation to be in compared to noncovered securities.

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Henry Delgado

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Has anyone else had issues with CashApp Taxes not accepting "Various" as an option for acquisition date? I'm having the same merger stock issue but the software keeps forcing me to enter a specific date!

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Olivia Kay

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Try entering the date of the merger instead. That's what I did last year with a similar issue in TaxAct and it worked fine. For CashApp specifically, sometimes you need to select "I'll enter my own information" rather than using their guided walkthrough.

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Henry Delgado

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That worked! I had to switch to the manual entry mode and then it let me type "Various" in the field. Thanks for the tip!

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