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

**URL:** <https://community.clark.com/t/how-do-you-know-when-you-have-to-pay-estimated-taxes/7767>\
**Category:** Uncategorized\
**Created:** [June 3, 2025, 4:57am UTC](https://community.clark.com/t/how-do-you-know-when-you-have-to-pay-estimated-taxes/7767 "2025-06-03T04:57:51Z")\
**Posts on this page:** 3\
**Page:** 1

<div class="post-metadata">

**Author:** ![AustinBonds](https://avatars.discourse-cdn.com/v4/letter/a/6bbea6/32.png) [@AustinBonds](https://community.clark.com/u/AustinBonds)\
**Post date:** [June 3, 2025, 4:57am UTC](https://community.clark.com/t/how-do-you-know-when-you-have-to-pay-estimated-taxes/7767/1 "2025-06-03T04:57:52Z")

</div>

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?

---

<div class="post-metadata">

**Author:** ![H200h](https://avatars.discourse-cdn.com/v4/letter/h/e79b87/32.png) [@H200h](https://community.clark.com/u/H200h)\
**Post date:** [June 7, 2025, 4:31pm UTC](https://community.clark.com/t/how-do-you-know-when-you-have-to-pay-estimated-taxes/7767/2 "2025-06-07T16:31:46Z")

</div>

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.

> **[Estimated taxes | Internal Revenue Service](https://www.irs.gov/businesses/small-businesses-self-employed/estimated-taxes)**
>
> Who must pay estimated taxes, how much to pay and when to pay them.

---

<div class="post-metadata">

**Author:** ![AustinBonds](https://avatars.discourse-cdn.com/v4/letter/a/6bbea6/32.png) [@AustinBonds](https://community.clark.com/u/AustinBonds)\
**Post date:** [June 8, 2025, 3:55am UTC](https://community.clark.com/t/how-do-you-know-when-you-have-to-pay-estimated-taxes/7767/3 "2025-06-08T03:55:47Z")

</div>

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.