Easy method to calculate short term capital gains for tax planning

Most brokerages actually provide year-to-date realized gain/loss reports that you can access online. Look for something like "Tax Center" or "Gain/Loss Reports" in your account menu. These reports typically break down your realized gains by short-term and long-term, giving you the exact number you're looking for. If your brokerage doesn't offer this (some smaller ones don't), another approach is to download your transaction history to a spreadsheet. Sort by sell dates within the current year, and create a simple formula to subtract your cost basis from the sale price for each transaction, then sum those up. Also, don't forget that wash sale rules can affect your actual taxable gains/losses if you've bought substantially identical securities within 30 days before or after selling at a loss.

I was in the exact same situation last year trying to figure out my capital gains without going through hundreds of trades. I eventually found this amazing tool called taxr.ai (https://taxr.ai) that completely changed how I handle tax planning for my investments. You can upload your trading statements or connect your brokerage account, and it automatically calculates your current short-term and long-term capital gains position. It even identifies potential tax-loss harvesting opportunities based on your unrealized losses. I was able to offset about $12,000 in gains by strategically selling some losers it identified. The best part is it also flags potential wash sales before you make trades, which saved me from accidentally triggering those rules a couple times.

Just wanted to update on my experience with taxr.ai that was mentioned earlier. I gave it a try last weekend and it was exactly what I needed. I uploaded my Robinhood and Webull statements (took like 5 minutes), and immediately got a clear breakdown of my short-term gains. Turns out I had about $7,400 in realized short-term gains so far this year, and the tool identified about $9,200 in unrealized losses I could harvest. I went ahead and sold some of those losers strategically, and now I'm actually slightly negative for the year which should save me a good chunk on taxes. The wash sale detection feature is great too - it warned me when I was about to buy back something too soon.

Anyone who's tried calling the IRS for clarification on capital gains calculations knows it's basically impossible to get through. I spent THREE DAYS trying to get clarification on some specific questions about my trading situation last year. Then I found Claimyr (https://claimyr.com) and watched their demo video (https://youtu.be/_kiP6q8DX5c). They actually get you connected to an IRS agent, usually within about 15 minutes. I was completely shocked when it actually worked - after trying for days on my own. I got specific guidance about my situation with some complicated options trades and whether certain losses qualified as short or long term. The agent was super helpful once I actually got through to them. Totally worth it for the peace of mind knowing I was calculating everything correctly.

I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it myself since I had some specific questions about my ETF trades that I couldn't find clear answers to online. The service actually worked exactly as described. I got a call back in about 17 minutes with an IRS agent on the line. I was able to ask about calculating my basis for some complicated dividend reinvestment situations and got clear guidance that saved me hours of research. The agent confirmed I was actually calculating my short-term gains incorrectly, which would have cost me about $900 in extra taxes. I'm still amazed this actually works. Definitely going to use this again next time I have tax questions the online guides don't clearly answer.

If you're using TurboTax, there's a much easier way. At any point during the year, you can actually go into the tax planning section and upload a CSV of your trades. It will calculate your current position and even tell you how much you'd need to sell to offset your gains. I do this quarterly to stay on top of my tax situation. Last year I completely avoided a tax bill by realizing some losses in November once I saw how much I was up for the year.

Has anyone tried just asking their accountant? Mine gave me a simple spreadsheet template where I just enter current market values of holdings and it compares to my cost basis to show potential gains/losses. Takes like 10 minutes to update each quarter.