OK to pay estimated taxes all at once?

You can do it that way if you want. You may be parting with a lot of cash before you have to, but it sounds like you already recognize that.

Last year I sent about 90% of what I expected to pay over the summer all at once. Ended up getting a little back from federal and owed a little too state. No "late fee" once I filled either.

quote:

---

I'd rather not deal with sending the IRS a new check every quarter

---

i'd rather not send any at all but sending all at once doesn't really make any financial sense.

You can absolutely send all four quarters up front.

It's when you pay in arrears (later in the year / at the deadline) when you are subject to underpayment penalties.

This of it this way. You owe the quarterlies on 4/15, 6/15, 9/15, and 1/15. If you pay them after this date, then you could be penalized. But if you pay them before this date, then they are still paid by the due date.

Even if you just send in a single check for all four quarters with your Q1 voucher, the "overpayment" from Q1 will just flow to the other quarters in consecutive order.