No.
The 10% penalty for failure to maintain HDHP coverage is invoked ONLY when you use the last-month rule in the previous year. If you had HDHP coverage for each of the months in the previous year, then there is no need for the last-month rule, thus, no need for Failure to Maintain HDHP Coverage penalty.
However, what do you mean by "retire"? If you mean, go on Medicare, it is normal for the Social Security Administration to back date your coverage for up to 6 months. Depending on your circumstances, this could mean up to 6 months of 2023, that you would not be eligible to contribute to your HSA.
So tell us what "retire" means and we will let you know how it affects you.
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