@barn3826 Your first sentence indicates that you aware of enrolling in Medicare due to the less than 20 employees requirement. So, I have interpreted your question differently. Essentially, is it an advantage to stay in your spouse's Plan for secondary coverage or buy a Medicare Supplement Plan for secondary coverage ( also a Medicare Drug Plan)? Or, simply enroll with a Medicare Advantage Plan. In addition to comparing the amount of the High Deductible Plan versus the cost of the Medicare Supplement Plan (including Medicare Drug Plan), you need to review how your spouse's plan coordinates with Medicare Parts A, B, and D. Does that HD Plan have a Non-Duplication provision? For example, if you are hospitalized in 2021, your Part A Hospital deductible is $1,484 (increases each year) for each benefit period. If your spouse's Plan has a $1,500 or more High Deductible, that Plan may pay zero ($0.00) inasmuch as you may not have exceeded the HD deductible. You will pay $1,484. As an alternative to the HD Plan, you may purchase a Medicare Supplement for a monthly premium (varies with insurance company) that will cover the Part A deductible ($1,484) as well as the Part B deductible ($203) and the amount that Part B does not pay the physician ( approximately 20% of Medicare determined charges). You will need to ask the HD Plan how the Plan covers prescriptions if Medicare is primary.