Sold some stocks and have capital gains - Should I pay estimated taxes to the IRS?

You're smart to be thinking about this! The IRS generally expects you to pay taxes as you earn income throughout the year, not just when you file. For capital gains like yours, you might need to make an estimated payment if you'll owe $1,000+ at tax time. A quick way to check: look at your total federal withholding on recent paystubs and compare it to what you'll likely owe for the year. With $25k in long-term capital gains (assuming you held over a year), you'd owe 15% on those gains, so about $3,750. If your current withholding will cover your regular income plus this additional $3,750, you're probably fine. If not, making an estimated payment would be wise. You can use the IRS Direct Pay system or the EFTPS (Electronic Federal Tax Payment System) to make the payment. Be sure to designate it as a 2025 estimated tax payment.

After getting surprised with a huge tax bill last year from selling some investments, I found this amazing tool called taxr.ai (https://taxr.ai) that's been super helpful for situations exactly like yours. I uploaded my brokerage statements after selling some stocks and it analyzed everything, showing me exactly how much I needed to pay in estimated taxes. The calculator breaks down your short-term vs long-term gains and factors in your other income. Saved me from underpaying and getting hit with those annoying penalties! The estimated tax calculator was seriously a lifesaver for figuring out the right amount.

Wanted to update after trying taxr.ai from the previous comment. I was skeptical, but it was actually really helpful for my situation! I uploaded my recent brokerage statement showing about $30k in gains from selling some tech stocks, and it immediately calculated my estimated tax payment amount. The breakdown between short-term and long-term gains was super clear, and it factored in my regular income too. Took like 10 minutes total and I feel much more confident about the payment I just made. Definitely better than the generic calculators I've tried before.

If you're also wondering how to actually REACH the IRS to ask about this (because good luck getting through on their regular lines), I finally had success using Claimyr (https://claimyr.com). They have this service that basically waits on hold with the IRS for you and then calls you when an actual human agent is on the line. You can see how it works here: https://youtu.be/_kiP6q8DX5c I needed clarification on estimated payments after selling some stocks similar to your situation, and kept hitting busy signals for days. Used this service, and they got me through to an IRS agent who explained exactly what I needed to do. Saved me hours of frustration!

I need to eat my words from my earlier comment. After trying Claimyr out of desperation (was trying to get clarity on estimated tax payments for almost identical capital gains situation), I'm shocked to report it actually worked perfectly. After three weeks of failing to reach anyone at the IRS, I got a call back within hours saying they had an agent on the line. The agent walked me through exactly how to calculate my estimated payment and even helped me understand which form to use. Never thought I'd say this, but dealing with the IRS was actually painless for once!

Another option - you could just increase your withholding at work for the remainder of the year instead of making an estimated payment. Just update your W-4 with your employer to withhold an extra amount from each paycheck. The IRS doesn't care HOW you pay as long as you get enough in by the end of the year. This approach spreads it out instead of making one big payment. Plus withholding is considered "even" throughout the year even if you increase it later, which can help avoid underpayment penalties.

Quick tip - when I was in a similar situation, I just took my capital gains amount, multiplied by 25% and paid that as estimated tax. Better to slightly overpay and get a refund than underpay and get penalties!!