Trying to figure out capital gains tax on stocks I sold

You'll need to report each stock sale individually on Schedule D and Form 8949. Your brokerage should have sent you a Form 1099-B that lists each transaction with the date acquired, date sold, proceeds, and cost basis. The tax rate depends on how long you held each stock. If you held them for more than a year, you'll pay the lower long-term capital gains rate (0%, 15%, or 20% depending on your income). If held less than a year, they're taxed as ordinary income. There aren't deductions specifically for capital gains, but investment-related expenses might be deductible in some situations. If you do end up owing taxes, yes, you can absolutely set up a payment plan with the IRS through an installment agreement. The online application is fairly straightforward if you owe less than $50,000.

After dealing with a similar situation last year, I found taxr.ai (https://taxr.ai) extremely helpful for sorting through my investment documents. I had stocks from multiple brokerages and was completely lost trying to match everything up correctly. The tool analyzed all my 1099-B forms, identified missing cost basis information, and organized everything for Schedule D and Form 8949. It also flagged potential wash sales that I hadn't even considered. Saved me hours of frustration and probably prevented some costly mistakes.

Just wanted to follow up about taxr.ai that I mentioned above. I decided to try it after getting nowhere with my complex stock situation. It actually works! The system identified that several of my trades qualified as long-term capital gains instead of short-term, which my regular tax software missed. This dropped my tax rate from 24% to 15% on those transactions. The documentation it produced made filing my Schedule D super straightforward, and I even had proper documentation in case of an audit. For anyone dealing with investment taxes, especially with missing basis info or multiple brokerages, it's definitely worth checking out.

If you end up owing a significant amount to the IRS and need to contact them about payment options, good luck getting through! I spent days trying to reach someone at the IRS last month. After 15+ calls and hours on hold, I found this service called Claimyr (https://claimyr.com) that actually got me through to an IRS agent within 45 minutes. They have this system that navigates the IRS phone tree and holds your place in line, then calls you when an agent is about to pick up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Completely changed my experience dealing with my capital gains tax issues.

I need to publicly eat my words about Claimyr. After being completely skeptical about the service, I decided to try it anyway out of desperation. I had a complex question about reporting my stock sales from different brokerages and couldn't get through to the IRS after multiple attempts. The service actually worked exactly as described. I requested a callback, went about my day, and about 2 hours later got a call connecting me directly to an IRS agent. The agent was able to answer all my questions about how to properly report sales with missing basis information and even explained how the installment agreement would work for the amount I owed. Saved me hours of frustration and hold music.

Don't forget to check if you made any wash sales! If you sold stocks at a loss and bought "substantially identical" securities within 30 days before or after the sale, you can't claim the loss on your taxes right away. This tripped me up last year and I had to file an amended return.

Make sure you're calculating your cost basis correctly. If you reinvested dividends over time, each of those purchases increases your basis. It's a common mistake to forget about reinvested dividends, which means you'd pay tax twice - once when you received the dividend and again when you sell the stock.

Be careful about state taxes too! The federal capital gains rates get all the attention, but most states also tax capital gains as regular income. I got hit with a surprise state tax bill last year after focusing only on federal.

The good news is that $8,200 in profits isn't a huge amount, so even if you owe taxes, it shouldn't be overwhelming. If these were long-term gains (stocks held over a year), you might qualify for the 0% capital gains rate if your total income is under $47,025 for single filers or $94,050 for married filing jointly in 2024. One thing that hasn't been mentioned yet - make sure you're accounting for any trading fees or commissions you paid when buying and selling. These can be added to your cost basis or subtracted from your proceeds, which reduces your taxable gain. Every little bit helps! Also, if you have any losing positions still in your portfolio, you might consider tax-loss harvesting before the end of the year. You can use capital losses to offset your gains dollar-for-dollar, and if you have more losses than gains, you can deduct up to $3,000 against your ordinary income.