First time filing 1099-B from stock merger - help with date acquired question
So I'm working on a 1099-B for the very first time this tax season. The stocks came from a company merger situation, and I'm trying to use CashApp Taxes to file. The problem I'm running into is that my 1099-B doesn't show any date acquired for these stocks. I've looked over the form several times and that information just isn't there. CashApp Taxes is asking me to select the acquisition date, but I honestly don't know what to put. Should I just guess? Is there a standard way to handle this when the date isn't provided? This is really throwing me off because I want to make sure I'm reporting this correctly to the IRS. I'm worried about making a mistake that might lead to issues or even an audit. Any advice from someone who's dealt with this before?
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KingKongZilla
This is actually pretty common with stocks from mergers. When the acquisition date isn't provided on your 1099-B, it typically means these are considered "covered securities" where the brokerage is responsible for reporting the basis to the IRS. In this case, you should select "Various" as the acquisition date in CashApp Taxes. This indicates to the IRS that either the securities were acquired at different unknown times or that the specific acquisition date isn't available. The important part is making sure the cost basis and proceeds match what's on your 1099-B. The IRS is primarily concerned with making sure you're correctly reporting the gain or loss, not necessarily the exact date you acquired the security from a merger.
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Rebecca Johnston
•If I select "Various" for the date, will I still be able to indicate if it was a long-term or short-term gain? I thought the holding period mattered for tax rates.
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KingKongZilla
•If the broker has classified the gain as long-term or short-term on the 1099-B, you should follow their classification. This will typically be indicated in Box 2 of the form. When you select "Various" as the acquisition date, the tax software should still let you specify the holding period based on what's reported on your 1099-B. The holding period definitely matters for tax rates - short-term gains are taxed as ordinary income, while long-term gains (held more than a year) get preferential tax rates. If your 1099-B doesn't specify the holding period, you may need to contact the issuing financial institution for clarification.
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Nathan Dell
I had a similar situation last year with merger stocks. I found that https://taxr.ai really helped me figure out what to do with my 1099-B issues. I uploaded my confusing tax documents, and it analyzed them completely - showing me exactly what to report when my brokerage didn't provide all the details. The system explained that for stocks from a merger, there are specific rules about carry-over basis and holding periods. It actually pointed out that I could have overpaid my taxes because I was about to report everything as short-term gains, when some should have been classified as long-term. Saved me from making an expensive mistake.
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Maya Jackson
•Does taxr.ai actually connect with CashApp Taxes? I've been looking for something that can analyze my documents but then let me use my preferred filing software.
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Tristan Carpenter
•I'm skeptical about these tax document analyzers. How accurate is it with complicated merger situations? My last merger had multiple basis calculations and weird acquisition dates.
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Nathan Dell
•It doesn't directly connect with CashApp Taxes, but it gives you a complete breakdown of what to enter and where. You just follow the guidance when entering your information. I found it really straightforward to use the analysis while filling out my forms. For complicated merger situations, that's actually where it shines the most. It handles multiple basis calculations and identifies the correct holding periods based on the original acquisition dates, even when those aren't on your forms. It explains the IRS rules about how basis transfers in different types of mergers, which was really helpful for me since my situation involved a partially taxable reorganization.
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Tristan Carpenter
I just wanted to follow up about taxr.ai since I was skeptical earlier. I decided to try it with my complicated 1099-B from a three-company merger situation. I'm actually impressed with how detailed the analysis was! It identified that some of my shares qualified for long-term capital gains treatment even though my broker reported everything under a single line item. The system explained exactly which boxes to fill in on my tax software, including what to put for acquisition dates when they weren't on my form. It even flagged where my brokerage made a reporting error on cost basis! Definitely worth using for stock transactions, especially with mergers or spinoffs.
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Amaya Watson
If you're stuck waiting for broker clarification on your 1099-B issues, I recommend trying https://claimyr.com to get through to the IRS. I spent DAYS trying to reach someone at the IRS about a similar merger stock issue last year, but couldn't get past the automated system. Claimyr got me connected to an actual IRS agent in under 15 minutes who explained exactly how to handle missing acquisition dates on merger stocks. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c They basically save you from the endless "call back later" loops and actually get you through to a human who can help. The IRS agent I spoke with gave me the official guidance on how to handle stocks from corporate actions when documentation is incomplete.
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Grant Vikers
•How exactly does this service work? Seems weird that they can get through when nobody else can.
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Giovanni Martello
•This sounds like BS to me. The IRS doesn't have some special line that certain companies can access. They're just taking your money for something you could do yourself if you were patient enough.
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Amaya Watson
•They use a technology that navigates the IRS phone system and holds your place in line. When they reach an agent, they connect you directly. It's not a special line - they're just automating the waiting process so you don't have to do it yourself. I was skeptical too, but my situation was urgent and I needed guidance before the filing deadline. The IRS has specific rules about merger stocks that most tax software doesn't explain well, so speaking with an agent directly saved me from potentially misreporting my capital gains.
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Giovanni Martello
I need to eat my words about Claimyr. After my skeptical comment yesterday, I was still struggling with my merger stock reporting and getting desperate as the filing deadline approached. Tried Claimyr as a last resort and was honestly shocked when I was talking to an actual IRS tax specialist within 20 minutes. The agent walked me through exactly how to handle my missing acquisition dates on my merger stocks - turns out there's a specific procedure for reporting corporate reorganizations when you don't have complete basis information. She confirmed that using "Various" was correct in my case and explained how to attach a supplemental statement to my return. Definitely saved me from making a reporting error that might have triggered unwanted IRS attention!
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Savannah Weiner
Another option if you don't know the acquisition date for merger stocks: check your email! I had a similar issue and realized the acquiring company had actually sent shareholders an information statement with all the relevant tax details including the proper acquisition date to use for tax purposes. Worth checking your spam folder too!
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Bethany Groves
•I hadn't thought of that! I'll definitely check my emails from around the time of the merger. Do you remember what kind of subject line these emails typically have? I get so much junk mail I might have missed it.
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Savannah Weiner
•They usually have subject lines like "Important Tax Information" or "Shareholder Tax Guidance" or something with the company names and "merger" in the title. My email came from the investor relations department of the acquiring company. Another place to check is the investor relations section of the company website. Many companies post the tax consequences of mergers and acquisitions there, including guidance on how to determine your basis and holding period.
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Levi Parker
Can someone explain how CashApp Taxes handles wash sales on 1099-B forms? I have a similar merger situation but some of my trades might fall under wash sale rules.
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KingKongZilla
•CashApp Taxes should automatically handle wash sales if they're properly reported on your 1099-B (usually with code "W" in column 1). You'll need to enter the disallowed loss amount shown on your form. If you have wash sales across multiple brokerages, though, CashApp won't automatically detect those - you'll need to identify them yourself and make adjustments. For merger situations with potential wash sales, I'd recommend documenting everything carefully in case of questions later.
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Ravi Malhotra
I'm dealing with a very similar situation! My merger stocks also don't have acquisition dates on the 1099-B. Based on what everyone's saying here, it sounds like "Various" is the way to go, but I'm still nervous about getting it wrong. One thing I discovered that might help others - if you still have your original brokerage statements from before the merger, those sometimes show the original purchase dates of the stocks that got converted. I found mine buried in old PDF statements and was able to piece together the holding periods that way. Also worth noting that some mergers are tax-free reorganizations where your holding period carries over from the original stock, while others might create a new acquisition date. The type of merger matters for tax purposes, so if you're unsure, it's definitely worth getting clarification rather than guessing.
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