How do you know when you have to pay estimated taxes?

1

I may sell some holdings in the late autumn and realize long term capital gains from it. If my tax liabilities between my regular employment income and selling this asset are below $1000 when I file before next April 15, then I should not pay estimated taxes upfront thus?

2

An easy way to avoid tax payment penalties is to make sure you have withheld and/or prepaid 110% of the prior years tax bill, it’s called the “safe harbor rule.”

If you are talking about big numbers (over $500k) then you should see a tax advisor or be real good at deciphering the IRS rules.

3

Thanks. I am looking at late 2025 to do the transaction if I do it at all. Gives me until January 15 to pay estimated taxes. If I overpay, just have to wait maybe 2.5 months to get a refund.