2017 -> I have HDHP insurance for complete year. Got HSA account from BOA. I've contributed to HSA account as per annual limit.
In 2017 I've spent high amount on medical expenses.
In 2018 I've changed employer and got HDHP insurance and a new HSA account from TASC. I've contributed to my HSA account as per annual limit.
Can I perform a trustee-to-trustee transfer from TASC HSA to BOA HSA and claim the medical expenses that happened in 2017.
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There is no need to perform that rollover; you can probably pay for those 2017 expenses from the 2018 HSA (see below).
As you probably know, you can pay for only those medical expenses incurred after the start of the HSA. However, the new HSA acquires the establishment date of the old HSA as long as there was a nonzero balance in the old HSA at any time in the 18 months prior to the funding of the new HSA. (IRS Notice 2008-59 Q&A-41) In other words, a gap of up to 18 months is permitted. That requirement is probably met in this case since it appears likely that the old HSA did not yet have a zero balance more than 18 months before the new HSA was established (you'll have to check the dates). If this is the case, either HSA account can be used to pay for any medical expenses incurred after the old HSA was established.
There is no need to perform that rollover; you can probably pay for those 2017 expenses from the 2018 HSA (see below).
As you probably know, you can pay for only those medical expenses incurred after the start of the HSA. However, the new HSA acquires the establishment date of the old HSA as long as there was a nonzero balance in the old HSA at any time in the 18 months prior to the funding of the new HSA. (IRS Notice 2008-59 Q&A-41) In other words, a gap of up to 18 months is permitted. That requirement is probably met in this case since it appears likely that the old HSA did not yet have a zero balance more than 18 months before the new HSA was established (you'll have to check the dates). If this is the case, either HSA account can be used to pay for any medical expenses incurred after the old HSA was established.
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