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My understanding is if you are expecting to owe more than 2k in taxes you are supposed to pay quarterly estimate taxes.

If you don't you might pay a penalty interest rate on the taxes owed to the IRS (Not sure how much that interest rate is...)

If you make a significant capital gain after the last quarter estimate payment due date do you still get that penalty? Since it is gained after the cutoff date for submitting estimated taxes I would think not but want to be sure.

I'm also not really sure how or where to go to e-file estimated taxes to begin with... I was trying to find it on the IRS website but could only find an explanation of when you have to pay estimated taxes.

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    If this gain is one-time and you have withholding on your regular income at least equal to last year and not over $150k, you probably have a safe harbor from the penalty even if you wait until next April (but not later!) to pay. Mostly dupe money.stackexchange.com/questions/95767/… and more linked there and maybe money.stackexchange.com/questions/131736/… and money.stackexchange.com/questions/140351/… Sep 1 at 1:24
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    The interest rate for 2210 penalty is set per (calendar) quarter based on the Treasury market plus 3%; given current economic conditions for this year it is unlikely to be much more than 3% rate and it's applied separately for each (tax) 'quarter' so if you wait until April (worst case) it is about 2% of the tax amount not timely paid. Sep 1 at 1:28
  • Thanks @dave_thompson_085 combined those linked questions, your comment, and the answer below helped me with all my unknowns
    – hellyale
    Sep 1 at 16:04
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The last quarter estimated payment due date is Jan/15 - of the next year. You can’t make any gains for the past year after being already 15 days into the next year.
The same is true for every quarter - the due dates are on the 15th of the month following the quarter.

There are many ways to pay, the simplest is direct from your checking account (https://directpay.irs.gov/directpay/payment?execution=e1s1)

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