u/BullCallBrawler

▲ 2 r/tax

Hey friends, sorry for any confusion, but this is the backstory:

I got pretty lucky with my investments and made approximately ~$750k total gains last year as I sold some long held stock investments and some speculative Call Options and reconsolidated into more conservative investments (50% S&P 500, 20% Bonds, 20% Gold, 5-10% speculative investments).

I did not know that I could pay the upcoming tax year (FY25) in advance so I ended up owing ~$300k in taxes in State and Federal. This was paid in full since I had set it aside planning for Tax Day - but the issue is coming from this years 1040-ES payments.

Since the amounts were so large, I went with a licensed CPA to handle it, and they set-up a 1040-ES payment plan for this year of quarterly payments of ~$65k. I explained to them that several things lined up that allowed for this amount and that I don't anticipate returns like this in the near future and for my current portfolio allocation I might have about $5k in dividend income (and this amount is close enough that my W2 job tax allocation may cover or I can tax loss harvest the speculative investments). My CPA said that this plan sounds good, and that the 1040-ES payments are optional and that I don't have to pay them but that if things change in the future to do it to avoid penalties in the later quarters - which I plan to do going forward (I had no clue you could pay in advance til a month ago oops).

The issue, is that one of these 1040ES payments were placed on the Tax Day 04/15/2026 deadline - after I was told not to pay it. The funds were not there since I was told not to pay, and today I received a letter in the mail for the payment voucher and I'm still not sure if this is still optional or not as I have been calling the IRS call center every other day since Tax Day but cannot get an single representative to pick up.

Does anyone have any recommendations on what I should do?

Thanks!

**FWIW: There does not appear to be a balance on my account yet, but also my taxes are still being processed for this current year

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u/BullCallBrawler — 17 days ago