Roy recently commented on an article from financial-planning.com around IRA transfers into HSAs. He said:

“Clients who don’t expect to remain on a high-deductible health plan much longer, intend to job hop, or enroll in Medicare shortly may get bitten badly by the IRS if they make this move. That’s because when assets transfer from an IRA to an HSA they are subject to what’s known as a “testing period,” which begins the month the distribution is made and ends about 13 months later, says Ramthun. Clients who drop their high-deductible coverage and become ineligible to contribute to an HSA in that time face income tax on the full transferred sum and a 10% additional tax.”

This is a very insightful article that can be read on its entirety here:

https://www.financial-planning.com/news/moving-money-from-ira-to-hsa-the-only-time-it-makes-sense