Thanks, yes, you got it right with the second scenario, I made the contribution myself (my employer doesn't contribute any more for me now that I'm retired, but I still have the HDHP with HSA). The scenario you described is exactly what I did, and as you mentioned, as far as I'm concerned, there's little difference one way or another (as long as I don't over claim), since tax rates in the two states are not much different. But of course MA gets a little more tax than they "should", and NY gets a little less. Thank you again for the speedy response to my question!!!
