@RMenschel
Good information. Thanks.
@paulgk123
All Medicare says on its website is variations of "After that, your coverage start date will go back (retroactively) 6 months from when you sign up." It does not explain if that is when you apply or when you are approved or what. See When will my coverage start.
I am not certified as a Medicare expert, so I would have to defer that to someone who is.
"I knew about the 6 month retroactive period for Medicare A, " More precisely, it's up to 6 months, depending on how far away you are from your 65th birthday.
"So, definitely any contribution from March to June is now ineligible." Look carefully, March's coverage is what coverage you had on March 1st. I don't know how Medicare does this, but if they tell you that the Medicare coverage started on March 2nd or anytime after, then March is still an HDHP covered month.
"I discovered the pro-rated allowed contributions based on months of eligibility. " Yes, that is how it works.
" I would only be allowed two months of eligibility so my limit for 2020 would be 2/12 of ($3550+$1000) = $758? " Yes, that is correct.
"if my 2020 contributions were from me and from my employer, do I need to submit two requests for adjustment -- me directly to the fund and me to my employer? " No. When you go through TurboTax and indicate Self-only coverage for Jan-Feb and Medicare after that, TurboTax will indicate that you have excess contributions and ask you how much you want to withdraw by the due date of the return (May 17th unless you are in Texas, Oklahoma, or Louisiana).
Let TurboTax tell you the amount, then you contact the HSA custodian and ask for a withdrawal of excess contributions (use this exact phrase - or look for an online form on the HSA custodian's website that will let you ask for this online).
No need for two adjustments, just this one. Don't even tell your employer about this, because this does not affect them - the W-2 that they printed was correct and does not need to change.
TurboTax will automatically add back whatever part of the code W amount from box 12 on your W-2 that is in excess to line 8 on Schedule 1 (1040) so that it is taxed as it should be, and TurboTax will remove whatever part of the direct contribution (not through the employer) that was considered in excess from line 12 on Schedule 1 (1040).
Other than asking for the return of the excess contributions, all you will have to do is get the check from the HSA custodian and cash it.
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