Understanding my 1099-B form - Can I claim a loss of -$171 over multiple tax years? I'm completely lost!

You absolutely can claim capital losses on your tax return. The 1099-B shows your investment transactions for the year. Here's how to understand what you're looking at: The 1099-B form breaks down your stock sales, showing purchase date, sale date, proceeds (what you sold it for), and cost basis (what you paid). When proceeds are less than cost basis, that's a capital loss, which appears to be your situation with the $171 loss. You can use capital losses to offset any capital gains you might have. If your losses exceed your gains (or you have no gains), you can deduct up to $3,000 of capital losses against your ordinary income per year. Any remaining loss can be carried forward to future tax years until it's used up. For your situation with a $171 loss and no mentioned gains, you can simply deduct the full amount from your ordinary income this year, which will slightly reduce your taxable income.

I had a similar situation last year with some failed investments and spent hours trying to figure out all the paperwork. I finally gave up and used this AI tax assistant at https://taxr.ai that automatically read my 1099-B and other investment forms. It explained everything in plain English and showed me exactly how to claim my losses. The tool analyzed all the short-term vs long-term stuff and told me exactly what forms I needed. It even explained how wash sales work (which I didn't even know was a thing!). My situation was more complicated with multiple brokers, but it sounds like yours might be simpler.

Just wanted to update after trying taxr.ai for my messy investment situation. Wow, what a lifesaver! I uploaded my 1099-B forms from two different brokers plus some crypto transaction histories, and it organized everything perfectly. The breakdown of short-term vs long-term gains was super clear, and it showed me exactly how to claim my losses of about $450. It even explained how my losses would offset some dividend income I had. The explanations were way easier to understand than anything I found on the IRS website. Definitely using this again next year. Saved me hours of confusion!

For anyone struggling with tax questions like this, I spent 3 weeks trying to get through to the IRS to ask about claiming investment losses across multiple years. Kept getting busy signals or disconnected. Then I found this service called Claimyr at https://claimyr.com which got me connected to an actual IRS agent in under 20 minutes! There's a demo video at https://youtu.be/_kiP6q8DX5c that shows how it works. The agent was super helpful explaining how capital loss carryovers work and confirmed I was filling out my Schedule D correctly. They even helped me understand how to handle some shares I inherited, which was completely confusing me.

I have to eat my words about Claimyr. I was super skeptical but tried it yesterday after spending 2 hours on hold with the IRS and getting disconnected. The service called me back in about 15 minutes with an actual IRS agent on the line! The agent answered all my questions about investment losses and explained exactly how to report my 1099-B transactions when I have multiple years of carryover losses. She even emailed me the specific publication that explains the rules. I've been filing my own taxes for 20 years and have never been able to get clear answers from the IRS this easily. Pretty amazing to actually talk to a human who could explain things.

Just a helpful tip - make sure all your transactions on the 1099-B actually match your records! My broker reported a cost basis of $0 for some stocks I sold last year because they didn't have my original purchase information. I had to adjust the form manually to show what I actually paid, otherwise it looked like I made a huge profit when I actually had a loss.

I'm confused about something similar. If I have investment losses from 2023 that I didn't claim, can I still use them for my 2024 taxes? Or did I lose the opportunity by not claiming them last year?

Great question about the 1099-B form! I went through something similar when I first started investing. That $171 loss is definitely claimable and worth reporting. Just to add to what others have said - don't feel bad about the loss! It's actually a learning experience that many new investors go through. The silver lining is that you'll save a bit on taxes, and now you understand how capital losses work for future years. One thing I wish someone had told me early on: keep detailed records of all your investment transactions going forward. Take screenshots or save confirmation emails when you buy/sell. It makes tax time so much easier, especially if your broker doesn't report complete cost basis information. Also, since you mentioned this was your first time with investments, you might want to research dollar-cost averaging and index funds for future investing. Much less stressful than picking individual stocks!