Trying to figure out capital gains taxes on stocks sold last year

You only pay taxes on the profit (capital gains), which is the difference between what you sold the stocks for and what you originally paid (your cost basis). And yes, the holding period definitely matters! If you held the stocks for more than a year before selling, those are long-term capital gains and are taxed at preferential rates (0%, 15%, or 20% depending on your income bracket). The stocks you held for just a few months would be considered short-term capital gains and are taxed at your ordinary income tax rates, which are typically higher. Your 1099-B should show both your proceeds (what you sold for) and your cost basis for each transaction. If the cost basis isn't reported to the IRS, you'll need to provide that information yourself on your tax return. You'll use Schedule D and Form 8949 to report all of this.

After struggling with capital gains reporting last year, I discovered this amazing tool called taxr.ai (https://taxr.ai) that saved me so much confusion. I was exactly in your position - sold a bunch of stocks, got a complicated 1099-B with pages of transactions, and had no idea how to properly report everything. The tool basically analyzed my tax documents, including that confusing 1099-B, and showed me exactly what to report where. It even helped me identify some wash sales I didn't know about that would have gotten me in trouble. The best part was it showed me which transactions qualified for long-term vs short-term treatment.

Update: I tried taxr.ai after seeing it mentioned here and wow - it was exactly what I needed! My situation with mixed investment types would have been a nightmare to sort through manually. The system automatically separated my long and short term gains, identified which transactions had missing basis information, and generated all the forms I needed. Saved me hours of frustration and probably prevented some expensive mistakes. Definitely recommend for anyone dealing with investment sales!

If you're struggling with capital gains questions and need to talk to someone at the IRS directly (which I highly recommend for complex situations), try using Claimyr (https://claimyr.com). I was banging my head against the wall trying to get through to the IRS about some cost basis issues with inherited stocks. Called for WEEKS and kept getting the "due to high call volume" message and disconnects. Claimyr got me through to an actual IRS agent in under 45 minutes when I'd been trying unsuccessfully for days. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone tree and wait on hold for you, then call you when an agent is ready. The IRS agent cleared up my capital gains questions immediately and saved me from making a costly mistake on my return.

I need to publicly eat my words! After dismissing Claimyr as likely bogus, I was desperate enough to try it yesterday with my capital gains reporting problem. Within 35 minutes I was talking to an actual IRS tax specialist who walked me through exactly how to handle my missing cost basis situation. She confirmed I was doing the right thing by estimating my basis and keeping my purchase records. Would have spent hours on hold (or more likely, getting disconnected repeatedly) without this service. Sometimes being proven wrong is a good thing!

Don't forget to check if any of your stock sales qualify for tax-loss harvesting! If some of your stocks sold at a loss, you can use those losses to offset your capital gains. You can offset up to $3,000 of ordinary income with remaining capital losses, and carry forward any additional losses to future tax years.

Has anyone used the cost basis feature in H&R Block? TurboTax was giving me errors when I tried to enter some of my stock transactions that had wash sales. Wondering if another software might handle it better.

Just wanted to chime in with some additional perspective on the software discussion. I've used both TurboTax and H&R Block for capital gains reporting over the years, and honestly both have their strengths and weaknesses. One thing I learned the hard way is to always double-check that your software is properly handling wash sale adjustments. I had a situation where I sold stock at a loss and bought similar shares within 30 days, creating a wash sale. The software I was using at the time didn't catch it automatically, and I ended up having to file an amended return when I realized the mistake. Also, if you're dealing with a lot of transactions, consider getting the physical forms (Schedule D and Form 8949) and doing a few by hand first to understand the process. It helped me catch errors in my tax software and gave me confidence that everything was being calculated correctly. The IRS website has good examples of how to fill these out properly.