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If you enroll in Medicare at age 65 there is no penalty for the last 6 months of HSA contributions. 

If you delay enrollment in Medicare, there likely will be a penalty for HSA contributions made within the past 6 months.

Why is there a penalty?

The reason for the penalty is your Medicare Part A coverage back-dates 6 months whenever you decide to enroll the part A will be retroactively effective.  

See https://www.medicare.gov/sign-up-change-plans/how-do-i-get-parts-a-b/should-i-get-parts-a-b for additional information.  

Excerpted section from the Medicare website re: this answer: Premium-free Part A coverage:

• Begins 6 months back from the date you apply for Medicare (or Social Security/RRB benefits). To avoid a tax penalty, you should stop contributing to your Health Savings Account (HSA) at least 6 months before you apply for Medicare.
• Begins no earlier than the first month you were eligible for Medicare.

How can I avoid a penalty on my HSA contributions:

If a Reliant employee delays enrollment of Medicare past age 65, is the responsibility of the Reliant employee to notify Reliant of their decision to enroll in medicare 6 months prior to the enrollment, so that we can stop all HSA contributions. 

See Solomon excerpt from HSA page: https://solomon.reliant.org/display/fieldbenefits/HSA+-+Health+Savings+Account

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