I did a 1-time rollover from my IRA to my HSA in 2021, but there appears to be no way to enter this information to TT desktop in the HSA section. How do I handle this?

[kooolerking]

The HSA section instructions specifically say to not enter this amount to the personally made HSA contributions, so where does it go?

[VolvoGirl]

You should have a 1099R for the IRA.  After you enter it it asks what you did with it.

Enter a 1099R under

Federal Taxes Tab or Personal (Home & Business)

Wages & Income at the top

Then scroll way down to Retirement Plans and Social Security,

Then IRA, 401(k), Pension Plans (1099R) - click Start or Revisit

If you are filing a Joint return be sure to pick which person it is for.

Don't enter the bank or broker name and don't try to import it.  It is just as fast and easy to manually enter it.  At the bottom pick -  Change How I enter my Form

Then on the next screen pick I'll Type it in Myself

[kooolerking]

That's the problem ... after entering the 1099R info manually, for what I did with the funds, it only gives me (2) choices "moved money to another retirement account" or "something else". For either choice, it never prompts me with any option to show it was rolled-over to an HSA, so I am still stumped. At this point, it is treating the rollover to the HSA as if it was income rather than a non-taxable event.

There seems to be a serious lack of detail for this section like there is a drop-down menu missing. FYI - I am using TT Premier, Mac version, 2021. Any ideas?

[kooolerking · Accepted solution]

After many hours of troubleshooting, I found a bug (or undocumented "feature") in the TT 2021 Premier software for Mac that was causing the issue with the inability to enter information for an IRA-to-HSA rollover. This is what I did that finally "fixed" it today;

1) Performed the daily download and update to the TT software

2) I deleted the original 1099-R that reported the IRA distribution and then re-imported it

3) I manually checked the 1099-R "corrected" box in TT (it was blank after the import)

After doing the above, TT then presented to me screens that were previously hidden (or missing) that offered the option to select "Did you move money from traditional IRA into an HSA?", etc.

I'm not sure which step above finally allowed this hidden IRA-to-HSA rollover screen to finally display, but I recommend to the TT tech support and code developers to allow a trouble-shooting mode for TT users to disclose such conditionally hidden screens so we can find them quicker / easier in the event of a software glitch or issue with checked vs. unchecked boxes on imported forms. Thank you.