Do I need to report each stock sale on my 1099-B separately or can I combine them?

I just got my 1099 consolidated statement from Fidelity and I'm totally confused about how to handle my stock sales on my tax return. The 1099-B shows I sold 2 different stocks this year with a combined loss of about $0.26 (yeah, not exactly a big trader lol). I'm using Sprintax for my tax filing this year, and I'm not sure if I need to enter each stock sale as a separate transaction or if I can just combine them into one entry with the total loss. The form seems to want individual entries, but that seems excessive for such a small amount. Does anyone know the proper way to report these stock sales? Should I be listing each transaction separately on different 1099-B entries even though the loss is so minimal? Or is there a simpler way to handle this for small amounts?

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20 comments

Ravi Choudhury

•8M

When it comes to reporting stock sales from your 1099-B, you technically should report each sale separately. This is because the IRS wants to match what your broker (Fidelity) reports to them with what you report on your tax return. The good news is that most tax software, including Sprintax, should allow you to import your 1099-B information directly from Fidelity, which will automatically separate each transaction. If you're entering manually, yes, you should enter each stock sale separately with the correct acquisition date, sale date, proceeds, and cost basis for each. Even though the loss is tiny (only $0.26 total), the proper reporting method remains the same. You'll report these on Form 8949 and then transfer the totals to Schedule D.

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Ravi Choudhury

•8M

For taxpayers with numerous stock transactions, there are a few options that can save time. If all your transactions are properly reported to the IRS (covered transactions with basis reported), you can use the summary method where you can report totals for short-term and long-term transactions rather than listing each one separately. Many tax software programs also have direct import features that can automatically pull in all your transactions, even hundreds of them, without manual entry. Check if Sprintax offers this feature for Fidelity accounts, as it can save hours of data entry.

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Freya Johansen

•8M

I had a similar situation and discovered taxr.ai (https://taxr.ai) which saved me tons of time with my investment reporting. I had way more transactions than you (about 25 sales) and was getting frustrated manually entering each one. Their system can analyze your 1099-B and automatically identify and categorize all your transactions correctly. You just upload your tax documents and it extracts all the data you need. For stock sales specifically, it properly separates short-term and long-term gains/losses and makes sure everything matches what the broker reported to the IRS, which helps avoid those dreaded mismatch notices.

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Freya Johansen

•8M

Yes, it definitely works with crypto transactions too. The system is designed to handle all types of investment reporting including stocks, bonds, options, and cryptocurrencies. It can process the various forms that report crypto transactions. Regarding security concerns, I was cautious about that too initially. They use bank-level encryption for all document uploads and processing. The time savings compared to direct imports depends on your situation - if your broker offers perfect direct imports to your tax software, there might be less benefit. But in my experience, those direct imports often have errors or missing information that still requires manual fixes.

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Chloe Wilson

•8M

Just wanted to follow up about taxr.ai that I mentioned earlier - I decided to try it after all for my complicated mix of stock and ETF sales. Honestly, it worked way better than I expected! I uploaded my Fidelity 1099-B with 30+ transactions and it extracted everything perfectly, even identifying wash sales that I wouldn't have caught. The time savings was significant - took maybe 10 minutes versus the 2+ hours I spent last year doing manual entry. The best part was that it organized all my transactions into the right categories for the 8949 form, so I felt confident everything matched what Fidelity reported to the IRS.

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Diego Mendoza

•8M

If you're having trouble reaching the IRS to ask questions about your 1099-B reporting, try Claimyr (https://claimyr.com). I used it after waiting on hold for over 2 hours trying to get clarification about reporting multiple stock sales. Their service got me connected to an IRS agent in about 15 minutes instead of the usual endless wait. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with confirmed that yes, technically each sale should be reported separately, but also explained some shortcuts for reporting multiple similar transactions that saved me a ton of time.

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Diego Mendoza

•8M

It uses a callback system that monitors the IRS phone lines and calls you when an agent is about to be available. They don't jump the queue - they just hold your place in line so you don't have to stay on the phone yourself for hours. The service really does work as advertised. They use technology to navigate the IRS phone tree automatically and then monitor your place in the queue. When you're getting close to speaking with an agent, you get a call connecting you directly. No more listening to the same hold music for hours while attempting to multitask.

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StellarSurfer

•8M

Well, I have to eat my words about Claimyr. After my skeptical comment, I decided to test it myself since I needed to ask about stock reporting requirements anyway. I was absolutely convinced it wouldn't work and was ready to demand a refund. To my complete shock, I got connected to an IRS agent in about 20 minutes. The agent confirmed I need to report each stock sale separately but said for very small amounts (like your $0.26 loss), the IRS isn't going to come after you if you consolidate similar transactions. She also walked me through some shortcuts for reporting multiple transactions that my tax software wasn't making clear. Saved me hours of research and uncertainty. Sometimes being proven wrong is actually a good thing!

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Sean Kelly

•8M

No, I'm not a tax professional, just someone with experience filing my own taxes with investments for many years. You're right that the automated matching system exists, but in my experience, small discrepancies often don't trigger notices, especially when the net result (total losses or gains) matches. That said, if you want to be 100% compliant and avoid any possibility of automated notices, then yes, report each transaction separately. For two transactions, it's not much extra work anyway. I was thinking more of situations with dozens of small trades where the work multiplies significantly.

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Theodore Nelson

•2M

For your specific situation with just 2 stock sales and a $0.26 loss, I'd recommend entering them separately to be completely compliant. Since it's only 2 transactions, the extra work is minimal compared to the peace of mind. However, I want to address something important that others touched on - Sprintax is generally designed for non-resident tax filing and may not be the best choice if you're a U.S. resident with investment income. Most major tax software like TurboTax, FreeTaxUSA, or H&R Block have much better investment reporting features including direct imports from Fidelity. If you're stuck with Sprintax for other reasons, you'll likely need to enter each transaction manually with the sale date, purchase date, proceeds, and cost basis for each stock. Make sure the total matches exactly what's on your 1099-B to avoid any automated matching issues with the IRS. The $0.26 loss will carry forward to future years if you can't use it this year, so it's worth reporting correctly even though the amount is small.

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Ethan Anderson

•2M

This is really helpful advice, especially about Sprintax potentially not being the best choice for investment reporting. I'm actually a U.S. resident but chose Sprintax because it was cheaper - now I'm wondering if I should switch to something like FreeTaxUSA for better investment features. One quick question - when you mention the $0.26 loss carrying forward, does that actually make any practical difference? Like, will I ever realistically be able to use such a tiny capital loss against future gains?

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