2nd time Amending using Turbo Tax not working, and Can I file my current year tax before I do the amend for last year ?

[prda0401]

I have following questions, can somebody please help answer. 

1. I need to amend my tax return 2nd time for 2023, is this possible in web version of Turbo Tax or should I need to get a Desktop version?

background: Back in march 2024, I had to amend my 2023 tax return and it was successfully processed. I just found a 1099R for a rolled over retirement account from 2023 and so need to amend my 2023 tax return again. I tried to do this on web version of Turbo Tax (2025). And the numbers do not look right as well as Turbo Tax goes into an error loop and does not show what the actual issue is. I connected to an agent on Turbo Tax and after some time of troubleshooting I am advised to purchase a Turbo Tax Desktop version for 2023, then import my 2022 tax filing document and redo the 2023 tax return and to then amend it. Is this accurate?  It's a lot of work so wanted to confirm before I go down this path.

2. Also, Can I file my tax for 2024 before I do the ^ amend for 2023? If it's possible,( I guess), I will have whole year to figure out how to do another amend for my 2023 tax.

[DavidD66 · Accepted solution]

I'll address the easy one first:  Yes, you can file your 2024 tax return before you amend your 2023 return.

As for your 2023 tax return:  If the 1099-R you did not include on your 2023 tax return (original or amended) was Direct Rollover, with a Code "G" in box 7 of Form 1099-R, you might want to wait and see if the IRS sends you a letter about it.  If reported properly, it would not change anything on your tax return.  If you do receive a letter from the IRS, you may be able to resolve the issue by writing a letter and explaining that you did indeed rollover the funds.  That said, you should be able to file a second amended return in TurboTax Online, but the phone agent is correct, the amend process for the second amended return will be a smoother one if you switch to Desktop.  But I would try dong nothing first.   

[prda0401]

Thanks @DavidD66 !

It makes sense to wait and see if IRS really needs me to amend my 2023 tax return. I have follow up questions.

1. If not reported would this be a bigger issue (then now) later down the road, say while taking distribution from this account?
2. Is there a typical timelines IRS would send a letter for something like this? I was thinking it would have been tax filing year which would be during 2024 or can it be anytime in future? 

Thank you for your valuable response!

[DavidD66]

No, it's not going to be a "bigger" problem down the road.  It won't change anything on your tax return.  You would basically be sending them a Form 1040-X with no changes and an explanation that you were amended to report that your rolled over your retirement plan, that was reported on Form 1099-R as a direct rollover.

If you do file an amended return, you can download a fillable Form 1040X and fill it out based on the prior amended return.  Provide the explanation and mail it in with a copy of the 1099-R.  Same thing you will do if you wait for a letter.  

The timeline for the IRS to send a letter?  If you owe, or are due a refund, usually within a year, but up to two years after filing isn't strange.  If you haven't heard from them by now, you probably aren't going to.  They aren't going to recoup a single dollar.  Of course, the IRS has had some very strange timelines lately.