Trad IRA Dist can I repay to a Roth w/o penalties?

[GWBSR]

Due to job/income loss I have had to take 2 distributions from my traditional IRA this year. I am receiving minimal unemployment benefits. No federal taxes withheld as of now and no state (TX) taxes to worry about. I am 47 and provide 24/7 care for my disabled (advanced Alzheimer’s) mother who lives with me. If I repay the distributions received and place or roll it into my Roth, will I still face the early distribution penalty?  That is a very very high penalty but I literally had no other choice given personal situations. $14k traditional IRA distributions in 2021 reported on 1099R. About $25k traditional IRA distributions taken so far this year. When and how are penalties paid? I also have a 1098T for just over $18K college tuition payments I made for my son’s full time education (living on campus). This is all extremely confusing and I am in financial stress. Thank you 

[dmertz]

The deadline for rolling over a distribution from an IRA is the 60th day following the date that the distribution was received, so it's too late to roll over the $14k of distributions made in 2021.  For these distributions you can use the education-expense exception to the early distribution penalty, so you'll owe the tax but not the penalty.

For the distributions made in 2022 you must take into account the one-rollover-per-12-months limitation.  You can roll one of them over to a traditional IRA, avoiding penalty and continuing to defer the taxes.  The others could be rolled over to a Roth IRA as Roth conversions within 60 days of the distribution since Roth conversions are disregarded with respect to the oe-rollover-per-12-months limitation, avoiding the penalty but paying taxes in 2022.

The underpayment penalty is part of your tax liability.  The US tax system is pay-as-you-go, so to avoid an underpayment penalty you need to pay estimated taxes or have taxes withheld sufficient to avoid the penalty.  Any excess tax paid or balance due is determined on your tax return.

https://www.irs.gov/businesses/small-businesses-self-employed/estimated-taxes

[GWBSR]

Wow, thank you very much!