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Deductions & credits
"So, since I had HDHP coverage all 12 months of 2020, I can keep my full year's contribution in the HSA, even if I (re)apply for Social Security (and therefore Medicare) in (say) April? "
I would wait until July. The problem is that if your Medicare is back-dated 6 months from April, then for November and December (at least) you would have had conflicting coverage, that is, even if you still had HDHP coverage in November and December, you will have to enter Medicare for those months if your Medicare get back dated to those months.
Please note that when doing your 2021 return, that you may still be asked "What type of HDHP coverage did [your name] have on December 1, 2020?".
When you truthfully answer Family or Self, you will be told that your coverage has lapsed and please answer these questions so that we can calculate your penalty.
But when you indicate that you had HDHP coverage for every month (one of the questions) in 2020, then TurboTax will realize that you did not need the last-month rule, so didn't need to be clear of Medicare in 2021. So no penalty will be calculated, which is what you want. It's just a bit disturbing, just don't be surprised but answer the questions, and you should be all right.
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