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I don't make estimated payments normally. So having to make one was "not anticipated". I think only once or twice in 25 years have I had an issue with this. This year could make three times, and this year the amount is significant (in the past I think I owed penalties less than $50 on the rare occasions I hit it).

Base on this answer, and the answer that you increased your 401(k) contribution this year, so you might have less tax withheld this year than last, it sounds like you're still working and having taxes withheld from your paycheck.

If that's the case, I would suggest that the simplest answer would probably be sure that you will have enough withheld from your paycheck to meet the safe harbor of withholding at least 100% of your 2018 tax liability (110% if your AGI is more than $150k). You can get your 2018 tax liability from line 15 of your 2018 Form 1040. Then, assuming your last paystub wasn't for a bonus or other irregular payment, check it for the amount withheld YTD, and the amount withheld from this paycheck. If the taxes that were withheld from that check are continued at the same rate for the rest of your paychecks, will you meet the safe harbor? If, so then you don't need to make any estimated tax payments - but you should be sure to have the money to pay the taxes in April.

If you won't meet the safe harbor, then you can fill out a new W-4 to have enough additional taxes to meet the safe harbor withheld.

Note: If you typically get a refund, then you are likely to already have enough being withheld to meet the safe harbor - but with all of the changes to tax laws the last couple of years, it's best to check if you are concerned you're going to going to be owe a lot of taxes for this year.

I'm not familiar with the "annualized method", so I will have to do some research.

The beauty of doing the withholding through your paycheck is that there are no timing issues with withholding - it's considered to have come in 'in sync' with your income, even if you have extra taxes withheld only a few months of the year.

The 'annualized method' is only required if you've made unequal estimated tax payments throughout the year. If you only make one estimated tax payment in a year, then, by definition, the payments throughout the year are unequal. You can read about the 'annualized method' in the instructions for form 2210.

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