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

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.

Per the third footnote at IRS web page

Need an extension? If you pay part ($1 minimum) or all of the tax you estimate you will owe using a debit/credit card, you will not need to file an extension form, such as Form 4868. Your payment will act as the extension.

I believe Congress told IRS to modernize their systems, including having a customer portal where people can sign in and see their tax status, make payments, etc. This biggest issue is that Congress doesn’t give enough funding to IRS to update their infrastructure, train its employees, and run operations. The IRS is barely functional on day to day operations, sucks at training and doesn’t even know where to start regarding technology. So basically, we have to deal with current system and mail a hard copy, file extension through third party, or pay a minimum amount using EFTPS.

And you know all of these things to be facts?

Do you know the IRS spent at least $815,000,000 in just the last three years on IT modernization? Nearly a billion dollars!

Does that seem high to you? They’re still working on moving away from a system they’ve had since they existed. Updating hardware alone likely costs hundreds of millions of dollars. Not to mention having to fix all these bugs in the transition from the IMF system, but no one who knows the IMF system well enough is around anymore.

Based on my limited knowledge of IT, where companies aren’t willing to shell out a lot at the front-end to get things fixed/updated, they end up spending significantly more trying to upgrade here and there - because the system never ends up working correctly together if it isn’t implemented with all aspects in mind. And the IRS (or any IT department) can’t implement a plan with all parts as part of the plan, unless they know they will have the money to continue with the implementation.

Whether it seems high (whatever that means), it’s nearly a billion dollars. Over three years. What has the IRS done with that money? And the tens of billions it’s had over the years to “modernize” its systems. Why did the system(s) crash?

You stated “Congress doesn’t give enough funding to [the] IRS to update their (sic) infrastructure…”

How much is enough? I have no idea; do you?

Most of us deal with the IRS once a year. Does it always have to be on the same day? For all of us? No wonder it crashed.

Is it better for us to fund NASA to send rockets to do whatever or better for us to fix the IRS? Either way, we are a trillion dollars farther in the hole every year, no?

I didn’t know which side you were coming from - whether they haven’t spent enough, or whether they spent too much. What I’m saying, again, based on relatively little IT knowledge, is that given the age of the current system, size of the system, security necessary, the necessity to only have data inaccessible for a very limited period of time, and the inability to simply temporarily move data to other servers while transitioning to a new system (see security), $1bn in 3 years for upgrades is not that unusual. But hopefully there’s someone here with IT experience in global conglomerates who may be able to chime in with a better opinion.

Don’t know. It’s possible they paid it out in questionable agreements that didn’t go through the appropriate government processes (which they’ve done before). All I’m saying is that $1bn to modernize the entire system isn’t that outrageous. Where are you getting this number? Perhaps that could shed some light into what they’re doing with it…

Don’t know, but the system issue (presumably you’re referring to the 4/17 problem) was with the e-filing system only (or so we’ve been told). It’s not uncommon for sites/systems to go down when overloaded. Could be many reasons (not enough bandwidth, bottlenecks at some point, etc.) Often times they don’t know it will crash until it does, but this happens all the time when there’s a one-time event that causes unusual overload. Companies will usually try to buy extra bandwidth to cover that, but it’s not always bandwidth that causes the issue and it can be hard to scale up other resources. And they won’t know what the issue is until they’ve gone through and determined what resource limits were hit.

No I didn’t. I also don’t know why you put “(sic)” after “their” given that that’s the proper spelling and use of the word.

No it doesn’t. You can e-file on any day from like March - April 15ish. You can also receive an automatic extension so you can e-file on any day from March - October 15ish. You can e-file on more days of the year than you can’t e-file on.

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Yes, you did. Go re-read your own post.