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.
