Preparing for Medicare
When to Enroll, What to Know & Avoiding Penalties
Clear guidance to help you make confident Medicare decisions at the right time.
When to Enroll
Your enrollment timing depends on your coverage– especially if you’re still working or contributing to an HSA.
Select the option that best describes your situation:
Not sure which applies? Complete our Medicare Questionnaire.
Before you Enroll
Prior to enrolling in Medicare, there are a few important rules that can significantly affect your timing, taxes, and premiums.
Cost Analysis
Comparing your Group Plan to Medicare
Before deciding to stay on your employer plan or move to Medicare, it’s important to compare the real numbers — not just the monthly premium.
A proper comparison looks at:
- Total annual premiums
- Deductibles and out-of-pocket limits
- Prescription costs
- Network flexibility
- Impact on a spouse or dependents
As a general guideline, if your group health plan costs more than $4,500 per year per person, it’s worth taking a closer look at how Medicare compares.
When You’re Ready to Enroll
If you’re planning to retire or transition to Medicare, reach out 4–8 months before your desired start date.
Starting early gives you time to confirm your enrollment window, coordinate any employer coverage, and review your options without rushing decisions.
Our advisors will guide you through each part of Medicare confidentially and help you choose the coverage that fits your needs and budget.
Visit the following pages for more information on plan options
Medicare Supplement Plan Options
Medicare Advantage Plan Options
Medicare Part D Prescription Plans