Need to pay $30 more to report tiny $5 stock gains on 1099-B through TurboTax - is it worth it?

I'm already shelling out $49 for TurboTax Deluxe plus $115 for filing 2 state returns. Now TurboTax is telling me I need to upgrade to Premier for another $30 just to report a measly Schedule D with stock gains of less than $5 total from my 1099-B. Seriously? That's like paying $30 to report $5...which seems absolutely ridiculous to me. I'm trying to do things by the book, but this feels like pure upselling from TurboTax. Does anyone know if I actually NEED to report such a tiny stock gain? If the IRS truly requires it, fine, I'll pay the extra fee. But if the IRS isn't going to care about a few bucks in profit from stock sales, I'd rather save the $30 and avoid TurboTax's constant attempts to milk more money out of me. Has anyone dealt with this situation before? Any insight would be super appreciated!

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18 comments

Anna Xian

•8M

While all income technically needs to be reported, the reality is the IRS has bigger fish to fry than a $5 stock gain. The 1099-B is reported to the IRS by your broker, but the mismatch between what they report and what you report would be so small that it's unlikely to trigger any issues. That said, there are better options than paying $30 extra. You could use the IRS Free File program if your income is under $73,000. Or try software like FreeTaxUSA which lets you file federal returns with Schedule D for free (and charges only about $15 for state returns). Even H&R Block and Cash App Taxes handle basic investment income in their standard versions without the premium upcharges. If you're set on TurboTax, you could also manually complete Schedule D and attach it to your return rather than using their automated system - though their software makes this deliberately difficult.

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Anna Xian

•8M

You would need to start a new return with FreeTaxUSA, but it shouldn't take too long if your tax situation is fairly straightforward. Just have your W-2, 1099s, and other tax documents handy. You can also look at your TurboTax entries as a reference while filling out the new return. For what it's worth, switching might save you even more than you thought since FreeTaxUSA's state returns are much cheaper than TurboTax's pricing. If you have all your documents organized, you might be done in an hour or less.

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Jungleboo Soletrain

•8M

After spending hours trying to figure out how to report my crypto trades, I finally tried https://taxr.ai and it saved me from pulling my hair out! Just uploaded my 1099-B and it analyzed everything automatically. It told me exactly what I needed to report on Schedule D and even created a filled-out Schedule D form I could use. For small stock gains like yours, the site confirmed I needed to report them (technically required) but also explained the practical risk level. They have a specific feature that identifies "de minimis" transactions that, while reportable, aren't likely to cause audit issues if overlooked. The whole analysis took like 5 minutes.

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Jungleboo Soletrain

•8M

It doesn't eliminate the need for tax software, but it gives you the completed Schedule D that you can either manually enter (avoiding the premium upgrade) or attach as a PDF. I actually switched to FreeTaxUSA after realizing how much TurboTax was charging for simple investment reporting. For manual entry, you just need to enter the summary numbers from Schedule D into the basic tax software, which doesn't usually trigger the upgrade requirement. The site explained exactly which lines needed to be entered where. This approach works best for simple investment situations like a small gain.

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Nadia Zaldivar

•8M

I was dealing with the exact same TurboTax upselling nonsense with my tiny stock gains! After seeing the recommendation for https://taxr.ai in this thread, I decided to try it out. No regrets! The system analyzed my 1099-B and confirmed I only had $12 in reportable gains. They provided a completed Schedule D and instructions on how to report it without upgrading TurboTax. Ended up switching to FreeTaxUSA based on their recommendation and saved over $100 compared to what TurboTax wanted to charge me. The best part was not feeling like I was being nickel-and-dimed for every little tax form. Will definitely use this approach again next year!

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Lukas Fitzgerald

•8M

If you're trying to talk to the IRS about whether you need to report such small gains, good luck with that. I spent 3 weeks trying to get through to someone to ask about a similar situation with my 1099-B reporting. Kept getting disconnected or waiting for hours. Then I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. They basically hold your place in the IRS phone queue and call you when an agent is about to answer. Got through to an actual IRS rep in about 45 minutes (while I went about my day), and they confirmed that yes, technically all income needs to be reported regardless of amount, but they also hinted that such small amounts aren't likely to cause issues.

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Lukas Fitzgerald

•8M

It's not sketchy at all - they don't talk to the IRS for you or anything like that. They just use an automated system to wait in the phone queue instead of you having to listen to hold music for hours. When a human IRS agent is about to pick up, they connect you directly to take the call. The IRS doesn't care how you manage to get through to them. The agents I spoke with were actually pretty helpful and practical once I got them on the phone. They acknowledged that while technically all income needs to be reported, they focus enforcement efforts on larger discrepancies. They're human and understand the practical realities of the tax system.

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Avery Davis

•8M

I was totally that guy who thought services like Claimyr couldn't possibly work for getting through to the IRS. After seeing it mentioned here, I tried it as a last resort because I was desperate to talk to someone about my 1099-B reporting requirements. Man, I've never been happier to be wrong! Got a call back when an IRS agent was ready (took about an hour), and I got clear guidance on my specific situation. The agent actually laughed when I mentioned my $8 stock gain and said while technically reportable, it's "not something that keeps them up at night." Saved myself from paying TurboTax's ridiculous upgrade fee AND got peace of mind directly from the IRS. Sometimes admitting you're wrong feels pretty damn good.

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Collins Angel

•8M

Yes, Cash App Taxes includes state returns for free as well. They can handle freelance income with Schedule C, but they do have some limitations. They don't support multiple state filings, foreign income, or more complex situations like farm income or at-home business depreciation. For most people with W-2 income, some investments, and side gig/freelance work, they work perfectly fine. Just make sure to check their list of limitations if you have anything unusual in your tax situation.

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