Questing about mailing and owing back taxes for multiple years

[drewsg]

1) I owe money $354 for 2015, $650 for 2016, and I get refunds for 2017 and 2018. Is there a way to calculate the money that I owe the IRS up front with penalties, or can I just mail in my 1040s and have the IRS send me a bill or work out a payment arrangement.

2) How should I mail it? Each year in separate envelopes, or should I buy one of those big envolope thingys that I can put all 4 years in there. 

[xmasbaby0]

Even TurboTax will not calculate the interest/penalties on your late tax due.  The IRS will calculate it and send you a bill later--after they receive your tax return and whatever payment you submit.

Each tax year has to be filed separately using the forms for the specific tax year.  They cannot be combined in any way--do not even put them in the same envelope when you mail them.  Software for past years is available back to 2016.  Any earlier years can only be prepared on paper forms by hand--and those refunds have been forfeited now.

The current online program can only be used for a 2019 return--no other year.  And if you did not file a 2018 return you will have trouble e-filing 2019.  When it asks for your 2018 AGI try using zero.  If zero does not work then you have to print, sign and mail 2019.

Online preparation and e-filing for 2018 is permanently closed.

To file a return for a prior tax year

If you need to prepare a return for 2016, 2017, or 2018 you can purchase and download desktop software to do it, then print, sign,  and mail the return(s)

https://turbotax.intuit.com/personal-taxes/past-years-products/

Remember to prepare your state return as well—if you live in a state that has a state income tax.

When you mail a tax return, you need to attach any documents showing tax withheld, such as your W-2’s or any 1099’s.  Use a mailing service that will track it, such as UPS or certified mail so you will know the IRS/state received the return.

Note:  The desktop software you need to prepare the prior year return must be installed/downloaded to a full PC or Mac.  It cannot be used on a mobile device.

If you are getting a refund, there is not a penalty for filing past the deadline.  If you owe taxes, the interest/penalties will be calculated by the IRS based on how much you owe and when they receive your return and payment. The IRS will bill you for this; it will not be calculated by TurboTax.

https://ttlc.intuit.com/questions/1900990-how-do-i-file-a-prior-year-tax-return

[Texas Roger]

There is no way to calculate it up front because only the IRS knows what the penalties and interest will be. You should go ahead and make payments with each tax return and then the IRS will bill you for the penalties and interest. 

You should mail each tax return separately and use a tracking service to make sure the IRS got them.  There is too much risk of the IRS not seeing all the returns when they are mailed together.

[drewsg]

Should I use a document mailer or just a standard envelope? does it matter?

[Texas Roger]

Standard envelope would be fine if you only have a few pages. Use the tracking service if you are able to safely get to a post office. 

[IllinoisDesign]

I'm in the same boat. Is it OK to mail them all out on the same day?

[xmasbaby0]

Sure--one trip to the mailbox is fine.  But do not combine different tax years in the same envelope.  Each one needs it own envelope.  Federal and state returns go to different addresses, too.

[fanfare]

go to the www.irs.gov, setup an account to see your balances owed for all those years.

https://www.irs.gov/payments/view-your-tax-account

[fanfare]

turbotax is not the only tax software.

other software still goes back to the years you mentioned, at very low prices, by the way.