Paying estimated taxes

Given how low the time value of money is right now though, it might be easier just to do an estimate for the year and make quarterly payments.
That's what I've done. I'm making even quarterly payments based on what I owed last year. I'm converting my Roth to the same threshold as last year, so I should be close. If I have a little more dividends or CGs I'll owe a bit more but no penalty due to safe harbor. If I have less, I'll get a small refund. Since I did most of my conversion early in the year, it works out well to do it this way rather than estimate what's really owed each quarter.

To whoever missed the 1Q payment, I would pay it ASAP and make the regular payments on the other quarters. You'll pay less interest that way. If you do it in thirds the rest of the way, you'll still be behind until that final payment so you'll own more in interest as the interest will accrue on the amount you are short.

Using that EFTPS system is very smooth. You can set it up for all year, you can view your payment history and upcoming payments, you can set reminders to tell you that a payment is coming to make sure you have money in your account it's being drawn from, and you can easily change payments if you situation calls for it. No worries of forgetting, check being lost in the mail, payment somehow credited to the wrong account, wondering if they really got it, etc.
 
We just have taxes withheld from our IRA withdrawal. So don't deal with q payments.
 
Yes, it is a bit of a chore, especially since the periods are not true calendar quarters as someone previously mentioned. Luckily, I can do some Quicken reports and get most of the info for each period. Even though I cuss to myself what a PITA it is to do, the reality is that it takes me less than an hour.

Given how low the time value of money is right now though, it might be easier just to do an estimate for the year and make quarterly payments.

The regular tax tables are easy enough. But the capital gains calculations have gotten pretty hairy over the past couple of years, and the AMT estimates aren't that easy either. I have to estimate all of these things to come up with a reasonable of all these taxes plus NIIT.

Fidelity actually gives excellent YTD tax information on their website, and the other stuff is just interest which I get from Quicken. So collecting the info is the easiest. Crunching it annualized is the tough part.

Right now I'm doing the safe harbor method because even though I don't own most of the tax until the end of the year, the total tax is still in the ballpark if not a little under what I end up owing. If I have a significant drop in taxable income one year, I'll switch to annualized.

Actually - I evaluate in January. And if I determine that I have already covered 90% of the prior year's taxes, I'll lower or skip my Jan 15 estimated payment. It's easier that way, because I have very close to all the numbers.
 
We just have taxes withheld from our IRA withdrawal. So don't deal with q payments.

Upping Federal tax-deferred withholding to also cover taxable withdrawals would work for Federal, but we don't currently access tax deferred accounts due to ACA income manipulation (retired early - will look at Roth conversions after reaching 65 in three years. Vanguard doesn't offer withholding on taxable accounts and also doesn't withhold for state on either taxable or tax deferred AFAIK.
 

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