Stock sale on 12/28/2023 but settlement date is 1/2/2024 - why isn't it on my 1099-B?
Title: Stock sale on 12/28/2023 but settlement date is 1/2/2024 - why isn't it on my 1099-B? 1 I sold some shares of my tech stocks on December 28th, 2023, trying to lock in some gains before year-end for tax purposes. The trade went through fine, but the settlement date was January 2nd, 2024 (because of the weekend and holiday). Now I'm looking at my 1099-B for 2023, and this transaction isn't showing up anywhere! From everything I've researched online, the trade date is what matters for tax purposes, not the settlement date. The only exception I've found is if you're short selling at a loss, which I definitely wasn't doing - this was just a regular stock sale from my long-term holdings. Has anyone dealt with selling stocks at the very end of the year before? Is this normal or did my brokerage mess something up? I'm freaking out a bit because I need to file my taxes soon and I don't want to report this incorrectly.
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Morita Montoya
8 This is actually a common issue at year-end. You're right that for most tax purposes, the trade date (12/28/2023) is what determines the tax year, not the settlement date (1/2/2024). Your brokerage should have included this sale on your 2023 1099-B since the trade occurred in 2023. It sounds like they might have incorrectly used the settlement date to determine which tax year to report it in. I've seen this happen before, especially with year-end transactions. You should contact your brokerage firm right away. They may need to issue a corrected 1099-B for 2023. Make sure to explain that you understand the trade date determines the tax year, not the settlement date, and ask them to verify how they're handling year-end trades. Keep documentation of your trade confirmation showing the 12/28/2023 date in case you need it for your records or if there's any question from the IRS later.
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Morita Montoya
•15 Thanks for the response. Do you think I should go ahead and file using the information I have (meaning I'd report this sale on my 2023 taxes even though it's not on the 1099-B), or should I definitely wait for a corrected form?
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Morita Montoya
•8 I would definitely contact your brokerage first before filing. You want your tax return to match what the IRS receives from your brokerage. If you report a sale that doesn't appear on the 1099-B they submitted, it could trigger a mismatch notice from the IRS. Most brokerages can issue a corrected 1099-B fairly quickly. If you're approaching the filing deadline and haven't received a corrected form, you might need to file an extension to give yourself more time. It's better to wait and file correctly than to create a potential mismatch problem that you'll have to deal with later.
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Morita Montoya
12 I went through something similar last year when I was using TaxScout to prepare my taxes. I had several trades that weren't showing up correctly on my forms. I used https://taxr.ai and it saved me a ton of hassle. Their system analyzed my trade confirmations and tax documents, then showed me exactly what was missing and how to report it. For your situation, they'd be able to confirm whether the trade should be on your 2023 or 2024 forms and help you get documentation to prove it if your brokerage is being difficult. Their AI can even generate a letter requesting a corrected 1099-B from your brokerage with all the right technical language.
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Morita Montoya
•17 How exactly does this work? Do I just upload my documents to them and they tell me what to do? I'm always hesitant about sharing financial docs online.
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Morita Montoya
•20 Is this actually better than just calling your broker? Seems like they would just tell you the same thing the tax expert above already said - that the trade date is what matters.
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Morita Montoya
•12 You upload your trade confirmations and tax documents to their secure platform, and their AI analyzes everything for inconsistencies. The whole system is encrypted and secure - I was hesitant at first too, but they explain their security measures on the site. The difference from just calling your broker is that taxr.ai gives you the exact documentation you need. My broker kept going back and forth about which year certain trades belonged in, but having the AI-generated analysis with specific tax code references finally got them to issue corrected forms. They can also help you file correctly if your broker won't cooperate.
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Morita Montoya
20 Just wanted to follow up about that taxr.ai service someone mentioned. I was skeptical but decided to give it a try since I was getting nowhere with my broker about missing trades. It was surprisingly helpful - uploaded my documents and it immediately flagged that my December trades were missing from my 1099-B and showed me the exact tax code that proves trade date (not settlement) determines the tax year. The best part was the letter it generated for me to send to my broker - included all the technical tax language and references. Got a corrected 1099-B within a week! Just wanted to share in case anyone else is dealing with this year-end trade reporting issue.
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Morita Montoya
13 If you can't get your broker to fix this quickly, I'd recommend Claimyr (https://claimyr.com) to get direct help from the IRS. I spent WEEKS trying to resolve a similar issue where my broker refused to correct a form. I finally used Claimyr to get through to an actual IRS agent instead of waiting on hold forever, and they confirmed the correct way to report it. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Basically, they get you through to an IRS agent usually within 15 minutes when normally you might wait hours or never get through. The agent I spoke with was super helpful and even sent me documentation I could show my broker.
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Morita Montoya
•19 Wait, this seems sketchy. How does some random service get you through to the IRS faster? Everyone has to wait in the same queue, right?
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Morita Montoya
•10 I've heard about these "get to the front of the line" services before, but do they actually work? The IRS phone lines are notoriously backed up, especially during tax season. What's their secret?
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Morita Montoya
•13 It's not sketchy at all - they use a completely legitimate process. The IRS phone system has different queues, and Claimyr uses technology to navigate these systems efficiently, then connects you once they reach an agent. You're still going through the official IRS channels, just with someone doing the waiting for you. Their secret is basically that they have systems continuously calling and navigating the IRS phone tree until they get through, then they connect you directly. I was skeptical too, but when I got connected to an actual IRS agent in about 15 minutes after spending days trying on my own, I was convinced. The agent confirmed everything about my trade date vs. settlement date question.
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Morita Montoya
19 I owe an apology about my skepticism regarding Claimyr. After continued frustration with both my broker AND trying to reach the IRS myself (2+ hours on hold before getting disconnected), I tried the service. I'm honestly shocked - I was connected to an actual IRS agent in less than 20 minutes. The agent confirmed that the trade date of 12/28/2023 is what matters, not the settlement date. She even provided me with the specific section of tax code to reference when contacting my broker. Having that official information from the IRS finally got my broker to issue a corrected 1099-B. If you're dealing with this issue and getting nowhere with your broker, it's actually worth trying.
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Morita Montoya
5 I've worked for a brokerage firm and can tell you this is a common problem with year-end trades. Your broker probably has an automated system that sorted your trade into the 2024 tax year based on the settlement date. One thing to check - log into your brokerage account and look at your 2024 tax forms. Some brokers have already generated preliminary 1099-Bs for 2024 that you can view online. If your December trade shows up there, that confirms they're using the settlement date incorrectly.
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Morita Montoya
•22 I never thought to check for preliminary 2024 forms! Just did, and sure enough, there's my December trade listed on my 2024 form. So frustrating that they got it wrong. What's the best way to approach them about fixing this?
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Morita Montoya
•5 Since you found the trade on your 2024 preliminary forms, that makes your case much stronger. Contact your broker's tax department directly (not just customer service) and specifically request a "corrected 1099-B for tax year 2023" to include the December 28th trade. Mention that you understand IRS regulations specify that trade date, not settlement date, determines the tax year for reporting purposes. Be prepared to provide your trade confirmation showing the December 28th date. If the first person you speak with doesn't understand, ask to escalate to a supervisor or tax specialist. Most brokerages can resolve this fairly quickly once you reach someone who understands the issue.
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Morita Montoya
3 Just be aware that even after you get your broker to fix this, you might face another hassle. Sometimes when brokers issue corrected 1099-Bs, the IRS computers flag the discrepancy between the original and corrected forms, and you could get a CP2000 notice asking about "unreported income." If that happens, don't panic! Just respond with copies of both your original and corrected 1099-Bs, along with a brief explanation that the correction was needed to properly report the December 28 trade in the correct tax year.
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Morita Montoya
•4 This happened to me last year! It was such a headache. The IRS sent me a notice claiming I owed an additional $2,300 in taxes because of a "missing" stock sale, but it was actually just reported in the wrong year. Took me three letters back and forth to resolve it.
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