How do I report a Roth IRA rollover made within 60 days that spans two tax years, i.e., money withdrawn in Dec 2018 and contributed to same account in Feb 2019?

[ljball]

I am 47 years old.  I withdrew money from my Roth IRA in December 2018 to make a downpayment on a construction loan for a custom home.  The money withdrawn included my full contribution basis, plus some earnings.  I instructed the Trustee not to withhold tax.  I intend to rollover the full amount of the funds withdrawn to the same Roth IRA within 60 days.     

[macuser_22 · Accepted solution]

A 2018 distribution will be reported on a 2018 1099-R that you should receive after Jan 31, 2019.   When you enter then 1099-R into TurboTax you will be asked what you did with the money - choose that it was rolled over.

The fact that it spans years is immaterial as long as it is within 60 days of the distribution.

Don't wait until the last day though, some financial institutions rules specify that the posting date (and the date they send to the IRS) can be several days after the deposit to allow for processing. 

[SteamTrain]

And if you wait until mid-March to finish and file your Federal/state tax returns, you will know by then whether you actually did the rollover, and can enter it all properly in your taxes for either situation.