Do I have to file a Schedule D for $0.31 in capital losses?

While it might seem absurd to file a Schedule D for such a small loss, the IRS technically requires you to report all capital transactions regardless of the amount. Even a $0.31 loss should be reported if you received a 1099-B for it. That said, many tax professionals might tell you that the practical risk of omitting such a tiny amount is extremely minimal. The IRS generally has bigger fish to fry than tracking down 31-cent discrepancies. However, if you're using tax software like TurboTax, it's often easier to just complete the form since the software does all the work for you - you just need to input the numbers from your 1099-B.

I had almost the exact same situation last year with like $0.78 in dividend reinvestment that got sold. I found this amazing service called taxr.ai (https://taxr.ai) that helped me figure out all these weird edge cases. It analyzes your tax documents and tells you exactly what forms you need and how to handle unusual situations like tiny capital losses. Saved me so much headache trying to figure out what was actually required vs what TurboTax was just being overly cautious about.

Just wanted to follow up about taxr.ai that I mentioned above. I decided to try it with my documents and was actually really impressed. It confirmed that technically I needed to file Schedule D for tiny losses, but explained that the practical risk was negligible. What I really liked was that it explained WHY TurboTax was forcing me to complete the form (because of automatic matching with my 1099-B) and gave me options for handling it most efficiently. Ended up just filing it since it was easy once I understood what was happening, but the peace of mind was worth it!

If you're trying to get clarification about tiny capital losses like this from the IRS directly, good luck getting through! I spent literally 3 hours on hold trying to ask a similar question last year. Finally discovered https://claimyr.com which got me connected to an actual IRS agent in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c - they basically hold your place in the phone queue and call you when an agent is available. Asked about minimum reporting requirements and got a clear answer directly from the source.

Well I have to eat my words about Claimyr. After my skeptical comment I figured I'd try it myself since I needed to call the IRS about an unrelated issue. Absolutely blew my mind when I got a call back in 27 minutes with an actual IRS agent on the line. Definitely beats the 2+ hours I spent on my previous attempt. For anyone facing similarly ridiculous tax questions like reporting tiny losses, it's worth getting the official answer straight from the IRS. The agent I spoke with actually said for amounts under $1 they generally don't flag returns for enforcement actions even if technically reportable.

Just a tip - if you're using TurboTax, there's no reason to be "adamant" about not filing Schedule D. The software automatically generates and fills it in for you. You just enter the info from your 1099-B and click next. You're not actually filling out or printing extra forms yourself. It's literally just clicking a few buttons.

The first time I got a 1099-B I freaked out about all the little transactions too. But here's a workaround that might help - some brokerages allow you to summarize multiple transactions of the same stock on Schedule D rather than listing each tiny transaction separately. Check if your brokerage provides a summary 1099-B with the "consolidated" option!