Any way to file an IRS extension online directly with the IRS?

The closest thing directly with the IRS online is probably paying $1 for 4868, which is applied to your tax anyway.

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FreeTaxUSA also offers free online extension

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There are three ways to request an automatic extension of time to
file a U.S. individual income tax return.

  1. You can pay all or part of your estimated income tax due and
    indicate that the payment is for an extension using Direct Pay,
    the Electronic Federal Tax Payment System, or using a credit
    or debit card. See How To Make a Payment, on page 3.

  2. You can file Form 4868 electronically by accessing IRS e-file
    using your home computer or by using a tax professional who
    uses e-file.

  3. You can file a paper Form 4868 and enclose payment of your
    estimate of tax due.

So you’re saying I could have paid a dollar and filed the extension electronically on EFTPS? Will have to remember that for next time.

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IRS says it will give US taxpayers an additional day to file returns after “system issues” Tuesday; new deadline to file is now Wednesday: “Taxpayers do not need to do anything to receive this extra time”

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One happy side effect of this is that you can still contribute to 2017 IRA’s today. Your custodian might need to do something manually. Schwab was able to manually backdate for me.

So pay1040 isn’t letting me use any additional cards to pay under the 4868 extension option. Any recommendations to get the additional funds in via Credit Card?

You’re bumping up against the limits from pay1040:
https://www.pay1040.com/Default/TaxPayerTools/FrequentlyAskedQuestions#question17

You’ll need to use another processor:

I need to file an extension, and pay taxes. Can I use Pay1040 and utilize multiple credit cards to pay the amount? I assume I can just keep sending payments attached to the social and the irs will see the multiple payments attached to my social?

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Might find info here:

Two things:

  1. no need to actually file an “extension” form if you make a payment.
  2. Credit card payments are supposed to be limited to two per processor (per payment reason, like regular 1040 or estimated payment, etc). In practice, the processor may not limit you to two payments. I’ve paid with 4x $500 debit card before with a single processor.

Additionally, wish me luck. Trying my first (larger) intentional overpayment. Overpaid by ~$9k

I did 2 payments towards the 4868 extension, but still need to send more money. Can I just use the 1040 option to get the rest in or recommendations - thanks bend3r

You’re bumping up against the limits from pay1040:
https://www.pay1040.com/Default/TaxPayerTools/FrequentlyAskedQuestions#question17

You’ll need to use another processor:

All good, went elsewhere and got it paid.

Anyways, tell me about what this extension does for me as I have never done one. Seems I have a few extra months to bring in a CPA and confirm numbers / tax strategies?

Also, is anyone that is an expert want to talk? Cheers

I’m skeptical about whether that’s allowed.

Don’t take my word for it, go to www.fidelity.com, they have a banner on the top of the page that shows “The IRS has extended the tax filing deadline. You have until 11:59 p.m. on Wednesday, April 18 to file and pay your taxes. Fidelity will accept your 2017 IRA contribution up until this deadline—please call 800-343-3548.”

Sorry, I didn’t mean to imply that you were incorrect that they offered it. I’m just saying that it may not be considered a 2017 contribution (regardless of whether the brokerage is willing to backdate it for you or not).

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I did some quick research before I took them up on it, seems pretty black & white so I went for it.