Proper way to file a 2nd Tax Extension? (for pre-paying more $, not extending time)

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Background:
For those who like to invest in I-Bonds, there's a $10K annual maximum individuals can purchase each year (through TreasuryDirect.gov), but an additional $5K can be obtained via an individual's IRS tax refund (so long as you have a $5K refund), enabling an individual to purchase/obtain up to $15K/yr in I-Bonds.

When you calculate your taxes, even if you owe the IRS money (or have less than a $5K refund), an easy way to create that $5K tax refund is to file an IRS form 4868 (Application for Automatic Extension of Time), paying your estimated tax bill (if any) + an additional (up to) $5K on or before the IRS tax due date (which fell on April 18, 2017 for tax year 2016).  If you're due a refund but it's less than $5K, you can still file form 4868, paying the IRS the additional amount needed to make your refund $5K.

If you estimate that you owe $123 in taxes to the IRS for a particular tax year, you can file for an extension, paying $5,123 (i.e. $123 + $5K) by the annual tax due date (so that you don't incur any penalties or late fees). Thereafter, when you file your taxes, you list your estimated payment of $5,123 on your 1040, ending up with a $5K refund, which you can then request as I-Bonds.

Issue:
If you file your 4868 extension, prepaying an initial estimated taxes amount (plus $5K) but find out later that your initial estimate was off (where you now owe an additional $456), this lowers your overpaid refund amount by that $456 (so you'd get less than the full $5K back in I-Bonds). If you're nonetheless intent on getting the full $5K of I-Bonds, what is the suggested way to pre-pay that additional $456 to the IRS for the PRIOR TAX YEAR?

From the googling I've done, it seems that a 2nd tax file extension (form 4868) is no longer allowed (barring certain circumstances, like a natural disaster), but even when it is, the intent seems to be for people who can't file by the 6 month extension date (which is around Oct 15 of each year).

In this case the 2nd extension is not to ask the IRS for more time but to simply pre-pay them more taxes (so that the resulting refund amount still comes out to exactly $5K). Would it be safe to file a 2nd Form 4868 (i.e. 2nd tax extension), or might it cause the IRS to lose track of what was sent in on the initial 4868? Would it be safer to file an estimated tax payment of $456 (Form 1040-ES) for the PRIOR TAX YEAR?  Any other suggested ways to safely pay that $456 so that it counts toward the PRIOR TAX YEAR?

Other:
For those who think it's foolish to invest in I-Bonds, that's noted but not the purpose of this thread.


TL;DR
If you sent the IRS a form 4868 (Application for Automatic Extension of Time), pre-paying a certain amount of taxes w/ that extension but want to increase that amount (by say $456) BEFORE filing your actual 1040, what's the suggested way to pay the IRS that additional $456 (for the PRIOR TAX YEAR)? Filing a 2nd Form 4868? Filing a 1040-ES for the PRIOR TAX YEAR? Other?

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Guess you were over at DA , eh?

castaline said:   Guess you were over at DA , eh?
If you're talking about a site/forum whose initials are DA, then I'm not familiar w/ it. If you want to PM me which forum that is (should they be better able to address my q), that would be appreciated.
  

I have never had to do second payment and cannot comment on that approach. You could file 1040 and request full 5K refund and once you receive the refund file 1040X amended return and show additional 456 due. This way you get 5K in I bonds and make 456 dollar payment with the amended return. You may owe interest on 456 due too late payment so it is in your best interest to file that amended return as soon as possible.

Matr0skin said:   I have never had to do second payment and cannot comment on that approach. You could file 1040 and request full 5K refund and once you receive the refund file 1040X amended return and show additional 456 due. This way you get 5K in I bonds and make 456 dollar payment with the amended return. You may owe interest on 456 due too late payment so it is in your best interest to file that amended return as soon as possible.That's why I'm seeking a way to pay the additional amount BEFORE filing the 1040, to avoid any interest or penalties.
  

copy paste  /   look about mid-postings / hope it helps

https://www.depositaccounts.com/blog/2017/04/april-series-saving...

castaline said:   copy paste  /   look about mid-postings / hope it helps

https://www.depositaccounts.com/blog/2017/04/april-series-savings-bonds-good-deal-compared-cds.html

Thanks for the link, but I failed to spot anything in the postings that discussed multiple Tax Extension payments.

That said, I found the following thread from 2013 w/ almost the identical issue as mine:
https://www.bogleheads.org/forum/viewtopic.php?t=111503

In that thread, the OP made an initial overpayment via a paper 4868 tax extension submission (snail mailing a paper tax form and paper check), only to be nailed by a revised 1099, raising his/her final tax bill. He/She made a 2nd tax extension (form 4868) payment electronically. The only "issue" the OP noticed was harmless:
ssss @ BoggleHeads said: Another update -- I received my savings bonds yesterday (dated March instead of February, but I'll survive). I also received an IRS letter stating they had to "adjust" my refund to $5019, which is exactly what my return specified, and everything in the "Your calculations" column marked the "IRS calculations" column exactly. So I'm not sure why they bothered sending the letter, but everything worked out as expected regardless.

I also found this link that gives the impression that multiple 4868's can be filed:
https://ttlc.intuit.com/questions/3922693-i-need-to-electronical...

Unless no other suggestions, I'll try my luck w/ a 2nd 4868 submission (where I do paper filing).

TheDiggler said:   I failed to spot anything in the postings that discussed
  
That wasn't the intent. It was to explain to us why you had a hardon to get I-Bonds.

Couldn't you just pay it as an estimated tax payment?  It may be late but I don't think the IRS makes a habit of refusing payments.  Form 1040-ES

caterpillar123 said:   Couldn't you just pay it as an estimated tax payment?  It may be late but I don't think the IRS makes a habit of refusing payments.  Form 1040-ES
I don't know, which is why I asked about that option in the OP.  I agree that the IRS is unlikely to refuse the payment, but whether that payment gets applies towards the PRIOR TAX YEAR is another question.

If, for example, I were to use 1040-ES voucher #4 for tax year 2016, one would hope that it would count for tax year 2016, but the normal course of events is to submit the 1040-ES (estimated tax payment) prior to the 4868 (Federal Extension).  Since the 4868 has already been submitted (and the IRS has already processed the check sent in w/ the 4868), I don't know whether a 2016 1040-ES filed after a 2016 4868 may inadvertently count as a 2017 estimated tax payment.  Thus the reason I started this thread.

  

There exists a form 1040-V.  I don't know whether it would be helpful for your situation, but you can read the instructions for the form and see whether it would be helpful.

Also, I see that the IRS suggests that the comment line of any check sent to them should indicate the year to which the payment should be applied.  However, I think you would also want to use a form that would correctly indicate the year to which the payment should be applied.
 

You should be able to make a balance due payment with a letter explaining how you want the payment treated. I have no idea what the effect of sending in a payment with a 1040-ES would be, and because of that I personally wouldn't do it. I'd probably call the IRS and ask them how to handle it. Why not just give yourself a bit of a buffer and pay $6k instead of having to worry about this?

TheDiggler said:   
Since the 4868 has already been submitted (and the IRS has already processed the check sent in w/ the 4868), I don't know whether a 2016 1040-ES filed after a 2016 4868 may inadvertently count as a 2017 estimated tax payment.  Thus the reason I started this thread.

 

  
This can happen in a normal situation. You're doing something a little unusual so its more likely to get screwed up in processing. The likelihood may not be high, but it goes up a bit. It could result in your refund getting held up if it has to go through some additional approval process. There have been times where I've found refunds held up with no IRS employee able to explain why. We actually saw a negative account balance in the record of account and no activity in the account since about a year after the due date so it wasn't a statute of limitations issue. So, these situations can happen (though probably rarely), you should take that into account in what you're doing.

What happens if you just make an additional epayment through one of the processors? Can't you just include it on the "total payments" when you file your return?

Endeavorer said:   There exists a form 1040-V. I don't know whether it would be helpful for your situation, but you can read the instructions for the form and see whether it would be helpful.I actually looked into the 1040-V (but didn't bother mentioning it in the OP). That's a form you're supposed to submit along w/ your actual 1040, but only if you owe $$$ to the IRS when filing taxes. I want to pre-pay the IRS additional funds (and see the check clear) BEFORE I submit my 1040, and I anyway don't owe the IRS $$$ at this point, so for those reasons I've ruled out the 1040-V. Thanks, though, for the suggestion.

marginoferror said:   I'd probably call the IRS and ask them how to handle it.I may give that a shot if time permits, but I can't spend hours on hold waiting for an agent to pickup.

marginoferror said:   Also, I see that the IRS suggests that the comment line of any check sent to them should indicate the year to which the payment should be applied. However, I think you would also want to use a form that would correctly indicate the year to which the payment should be applied.I always list the tax year in the memo line of a check, and I also use (or at least try to use) tax forms corresponding to the year I want the payment applied to.

marginoferror said:   Why not just give yourself a bit of a buffer and pay $6k instead of having to worry about this?Noted. Will do this in future years (but the above won't help with the current situation).

marginoferror said:   TheDiggler said:   Since the 4868 has already been submitted (and the IRS has already processed the check sent in w/ the 4868), I don't know whether a 2016 1040-ES filed after a 2016 4868 may inadvertently count as a 2017 estimated tax payment. Thus the reason I started this thread.
This can happen in a normal situation. You're doing something a little unusual so its more likely to get screwed up in processing. The likelihood may not be high, but it goes up a bit. It could result in your refund getting held up if it has to go through some additional approval process. There have been times where I've found refunds held up with no IRS employee able to explain why. We actually saw a negative account balance in the record of account and no activity in the account since about a year after the due date so it wasn't a statute of limitations issue. So, these situations can happen (though probably rarely), you should take that into account in what you're doing.
Whatever form I submit, I'll include a letter of explanation to the IRS of what I'm trying to accomplish. Hopefully that'll avoid any (significant) hold-ups on the IRS' end.



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