Intentionally overpaying taxes question

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In prior year I have filed an extension with an overestimate to overpay to convert to the 1.1X Amazon gift card.
This year I was instead wanting to get rid of some prepaid debit cards. (I have multiple Chase Freedom.  Get 5X = 8% minus 1% cost for debit card purchase and 1/2% charge by IRS for debit pay = ~6.5% profit with minimal effort).

Credit/debit are limited to 2 payments for extension and 2 payments for 1040.

I can, of course, do the same as last year and do an extension and overpay on it.  This would let me use 2x$500 cards.  I would then get the refund after efiling the actual 1040.

Alternately, can you just pay it applied towards the 1040 before filing?  Or, would that require me to "owe" on the 1040 that's filed.

Thanks for suggestions/experiences using the credit/debit payment options!

I've avoided estimated taxes in the past, but seems like a possible avenue in future years to lower employer withholding and do 2 estimated payments per quarter.  And this would let me to more easily avoid the underpayment penalty if I have capital gains in a year.

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You can do 2 payments per service x 3 services = 6 payments per calendar quarter for 2017 estimated.
Paying electronically something toward 2016 taxes automatically files 2016 extension according to several sources.

DoC comments on income tax payments with additional member comments

There are way easier ways to liquidate your prepaid cards.

Stubtify said:   There are way easier ways to liquidate your prepaid cards.
  An easier way to get the money direct deposited to my account after setting up a payment online for less than 1/2% fee?  Or you mean driving around possibly trying multiple stores YMMV in a particular chain by buying money orders if they let me?

Bend3r said:   
Stubtify said:   There are way easier ways to liquidate your prepaid cards.
  An easier way to get the money direct deposited to my account after setting up a payment online for less than 1/2% fee?  Or you mean driving around possibly trying multiple stores YMMV in a particular chain by buying money orders if they let me?

  Let's say you have 8 cards x $500.  On a single trip to WalMart, you could buy two $999.30 money orders (no paper work), and also make a $1999 bill payment to your CC account.  Cost of liquidation approx. 0.06%.

tuphat said:   On a single trip to WalMart .....

Impossible at the WalMart near me, even with rebate cards with my name on them.

Within the last year, one of the payment services treated a prepaid card as a credit card, so I had to choose a different payment service for that prepaid card. I don't remember the details. You may want to test a card before buying a lot of them.

I ended up just doing 3x$500 with extension. Official payments allowed more than 2 if done over the phone. I have to dig through some credit statements to see if a 2015 charitable contribution was charged in Dec 2015 or Jan 2016



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