I'm set to change employers. My last day of the old company will be 12/1 and I'll start at the new company on 12/11. I'll still have funds in my old HSA. Furthermore, I'll contribute to a new HSA at my new employer. Will I be penalized for that tiny window during my transition?
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IRS Pub 969 says:
Testing period. If contributions were made to your HSA based on you being an eligible individual for the entire year under the last-month rule, you must remain an eligible individual during the testing period. For the last-month rule, the testing period begins with the last month of your tax year and ends on the last day of the 12th month following that month (for example, December 1, 2016, through December 31, 2017).
However, section 223(c)(1)(A) of the tax code says:
(A) In general The term “eligible individual” means, with respect to any month, any individual if—
(i) such individual is covered under a high deductible health plan as of the 1st day of such month, and
(ii) such individual is not, while covered under a high deductible health plan, covered under any health plan—(I) which is not a high deductible health plan, and
(II) which provides coverage for any benefit which is covered under the high deductible health plan.
So, it appears that if you are covered by an HSA plan on the first of each month of the year you are considered an eligible individual for the entire testing period. It seems that you have indicated that you will still be covered by the old company's HDHP plan on 12/1, so you will be an eligible individual for December, as well as the earlier months of the year, but you'll want to confirm that. If that will not be the case, if COBRA continuation coverage is available from the old employer you could consider continuing the old employer's HDHP insurance for the month of December under COBRA. However, you would want to compare the cost of one month of COBRA to the tax and 10% penalty that would be due on the portion of your contribution made under the last month rule that you would not have been eligible to make were it not for the last-month rule.
IRS Pub 969 says:
Testing period. If contributions were made to your HSA based on you being an eligible individual for the entire year under the last-month rule, you must remain an eligible individual during the testing period. For the last-month rule, the testing period begins with the last month of your tax year and ends on the last day of the 12th month following that month (for example, December 1, 2016, through December 31, 2017).
However, section 223(c)(1)(A) of the tax code says:
(A) In general The term “eligible individual” means, with respect to any month, any individual if—
(i) such individual is covered under a high deductible health plan as of the 1st day of such month, and
(ii) such individual is not, while covered under a high deductible health plan, covered under any health plan—(I) which is not a high deductible health plan, and
(II) which provides coverage for any benefit which is covered under the high deductible health plan.
So, it appears that if you are covered by an HSA plan on the first of each month of the year you are considered an eligible individual for the entire testing period. It seems that you have indicated that you will still be covered by the old company's HDHP plan on 12/1, so you will be an eligible individual for December, as well as the earlier months of the year, but you'll want to confirm that. If that will not be the case, if COBRA continuation coverage is available from the old employer you could consider continuing the old employer's HDHP insurance for the month of December under COBRA. However, you would want to compare the cost of one month of COBRA to the tax and 10% penalty that would be due on the portion of your contribution made under the last month rule that you would not have been eligible to make were it not for the last-month rule.
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