TurboTax features

[insurance_engineering]

If I want to use the free version of turbo tax and want to file electronically, will I be able to attach .PDF file for 2 SSA-1099s and a 1099-R?  All 3 forms include voluntary tax withholding.  The 1040 form states that copies of the 1099s are required if there is voluntary tax withholding.  

[xmasbaby0]

No.  If you are e-filing your return you do not attach anything.  It is all done electronically.  You simply enter that information into the software and the data transmits with your tax return.  

Go to Federal> Wages & Income>>Retirement Plans and Social Security  (SSA1099 and 1099RRB) to enter your SSA1099.

To enter your retirement income, Go to  Federal> Wages and Income>Retirement Plans and Social Security>IRA  401 k) Pension Plan Withdrawals to enter your 1099R.

[insurance_engineering]

Last year I filed with a competitor product via e-file and my refund was delayed for months because the IRS sent a letter requiring the 1099s be submitted via reply mail with their letter attached.  I don’t want to have to go through that again!

[xmasbaby0]

@insurance_engineering You cannot attach pdf's to an efile.  If you want to attach copies of your documents you can file by mail.   You are only required to attach documents that show tax withheld when you mail a tax return.  

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.

Federal and state returns must be in separate envelopes and they are mailed to different addresses.  Read the mailing instructions that print with your tax return carefully so you mail them to the right addresses.

[SteamTrain]

@insurance_engineering 

Yeah, IRS requests to see the actual 1099-R forms, happens, but is quite rare.

Usually, it happens when the Federal withholding you reported doesn't match their own data....or when a provider (probably for the 1099-R) didn't send in their own reports on time, and the IRS has no record of those withholding $$ in your name and SSN from whoever issued the 1099-R to you  (the IRS gets separate withholding e-records from the issuer). 

Other than that, you could just have been one of the 0.1% of tax filers that got hit with a random check.