estimated tax question

I recently sold a bunch of I-Bonds that has generated a substantial income for the year.
Should I be paying estimated taxes on this? If so, what is the best way to go about doing this?
I used turbo tax for my 2017 return. Can I use that to generate a form to pay estimated taxes?
I was thinking of sending in a single lump sum of 50% of the income which should be enough to cover most of my investment income taxes for the year (not just what was generated from the sale of I-Bonds).
Thanks.
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This probably seems awfully retro but you can just fill out the form, print it, and mail it in with a check.
https://www.irs.gov/pub/irs-pdf/f1040es.pdf
If you have an EFTPS account you can log in and pay it all online.

The form 1040-ES PDF includes a worksheet to figure out how much to pay. Generally speaking you have to make timely payments of the lesser of 90% of what you owe or 100% of what you owed last year.
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On Wednesday, May 9, 2018 at 2:35:59 PM UTC-7, John Levine wrote:

I think this is good.

I don't have this.

This is really tough because between investment income and variable pay at work, there are huge changes year to year.
I think I will just print out voucher #2 from above and send in a fairly conservative payment that should cover my tax liability for the year (based on what I have been owing in past years and adjusting for current interest rates and redemption of I-Bonds). That should hopefully prevent any penalties from being levied and if any are levied, it would be small.
Looking at last year's return I paid $17.00 in penalty. Am I overthinking this? I am concerned that the penalty this year could end up being in the hundreds or more.
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Yes, you are definitely overthinking it. You can avoid all penalties for 2018 by making sure that all your withholdings and estimated taxes add up to at least 100% of the tax shown on your 2017 return (110% if your gross income is over $150,000, or $75,000 for a married individual filing separately). It doesn't matter how much you will actually owe for 2018.
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On 5/10/2018 10:13, anoop wrote:

You can pay electronically without EFTPS account.
https://www.irs.gov/payments/direct-pay
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Without our knowing your other income and deductions for the current year and how much tax you will have paid in without the estimated tax that you're considering, and knowing how much tax you were liable for in the prior year, it's not possible for us to advise whether or not it's a good idea for you to be sending in estimated taxes because of the taxable profit on whatever it was that you sold.
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On Thursday, May 10, 2018 at 11:13:37 AM UTC-4, anoop wrote:

Personally I don't pay any estimated taxes and wind up paying a few hundred every year; I used to make quarterly payments, but it was too much trouble. But it is just interest; there really isn't a penalty.
But sure, send in a payment if you feel better that way. You can either estimate how much you will owe, or pay 100% of last years as others said. If you pay too much, you will just get a refund.
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On Thursday, May 10, 2018 at 8:13:37 AM UTC-7, anoop wrote:

...

The above is what I ended up doing. However, I was surprised there was no acknowledgment from the IRS about the payment. The only proof that I have is the cancelled check. I unfortunately neglected to make a copy of the form before sending it in.
2 questions: - How can I find out if the IRS received and processed the payment correctly? - What is the correct way to report this on my tax return? In TurboTax, can I just add an entry for 2nd quarter tax payment with the date of the cancelled check?
Thanks.
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You can view your tax account online at the following link. It will show your payments for the last 24 months.
https://www.irs.gov/payments/view-your-tax-account

Yes, that's what you do. In the Find box enter "estimated tax payments" (without the quotes), then click the link that says "Jump to estimated tax payments." That will take you to the "Estimates and Other Income Taxes Paid" screen. Click the Start or Update button for "Federal estimated taxes for 2018 (Form 1040ES)."
The date of the payment is the date you mailed the check.
Bob Sandler
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You can get an online transcript of your IRS account here. The initial signup is a pain (as it should be), but once you're in, it's straightforward.
https://www.irs.gov/individuals/get-transcript

On the redesigned 2018 form, estimated tax payments go on line 66 on schedule 5, and are included in line 17 on the front page.
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Thanks Bob and John.
On Thursday, January 17, 2019 at 10:58:47 PM UTC-8, John Levine wrote:

I requested an account transcript for 2018 by mail. That way I didn't have to create an account. I should get it in 5-10 days.

It looks like TurboTax has done just that.
Thanks.
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You WANT to create an account, because that means nobody else can do so and pretend to be you.
There's a huge refund fraud problem due to crooks guessing enough info to get the victim's online transcript, then filing a fake return and sending the refund into the crook's account.
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On Sat, 19 Jan 2019 01:14:22 EST, John Levine wrote:

John, I followed your advice and created an account. I know that worked, because I could log off and then log in successfully, and it showed the site phrase and image I had selected.
But I can't get a transcript. On the page headed "Get transcript", I selected "Other" as the reason I want a transcript, and left Customer File Number blank since I'm not doing this for a lender. In the list of transcripts and years available, any year I click on does nothing -- no error message, nothing. I know there are active links, because if I hover on any of them a tool tip pops up, such as "2017 Record of Account Transcript".
Can you think of any reason why I wouldn't be able to get my transcript, after creating an account successfully?
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It could be that the site is broken, and there's nobody there to fix it because of the shutdown. I think I've seen some posts elsewhere saying that the transcript site isn't working. But this is just a guess.
Bob Sandler
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Beats me. I just logged in and the 2018 account transcript shows the three estimated payments I made in 2018. I presume after a while it will show the fourth payment I made last week.
The transcript is a PDF that opens in a separate browser window. Any chance your browser is helpfully blocking it as an unwanted pop-up?
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