Medicare Special Enrollment Period: Do You Qualify and How to Use It

Enrollment & Eligibility · February 2026 · 6 min read Medicare Special Enrollment Period: Do You Qualify and How to Use It Most people only know about the standard Medicare enrollment window. But life doesn’t always follow a schedule — and the Special Enrollment Period exists for exactly that reason. C Cindy Kowalski · Eligry … Read more

The Hidden Cost of a Free Medicare Advantage Plan — One Woman’s $150,000 Mistake

Medicare Plan Selection · February 2026 · 8 min read The Hidden Cost of a Free Medicare Advantage Plan — One Woman’s $150,000 Mistake Linda chose a zero dollar Medicare Advantage plan when she was healthy. Three years later, a kidney failure diagnosis revealed what that free plan would actually cost her over the next … Read more

When Should I Enroll in Medicare at 65 If I’m Still Working? Avoid Penalties & Costly Mistakes

Turning 65 + Still Working The right answer depends on your employer size, your coverage, and whether you contribute to an HSA. Here’s how to avoid costly mistakes and permanent penalties. Quick navigation Do I have to enroll in Medicare at 65 if I’m still working? Medicare doesn’t automatically know you’re working The 20-employee rule … Read more

Medicare Plan Changes 2026

C Cindy Licensed Independent Medicare Advisor · Eligry LLC · Updated February 2026 9 min read Medicare changed again for 2026 — premiums are up, some Advantage plans quietly cut benefits, and drug formularies shifted. Here’s exactly what changed, what it means for your costs, and what to review right now. Every year, Medicare changes. … Read more

The One Medicare Decision You Can’t Undo Later | Supplement vs Advantage at 65

The One Medicare Decision You Can’t Undo Later | Eligry LLC C Cindy Licensed Independent Medicare Advisor · Eligry LLC · February 2026 7 min read “What happens if your health changes?” That was the question my older sister asked me when I was turning 65. It’s the question most people never ask — and … Read more

Can I Switch from Medicare Advantage to a Supplement Later? What You Must Know Before You Decide

Medicare Plan Selection · February 2026 · 7 min read Can You Switch from Medicare Advantage to a Supplement Later? The honest answer is: sometimes. But not always. And that “not always” is where people get stuck — often permanently. C Cindy Kowalski Licensed Independent Medicare Advisor What You Must Know Before You Decide When … Read more

Medicare Supplement vs. Medicare Advantage: Why Your First Medicare Decision Could Impact You for Life

Medicare Planning Why Your First Medicare Decision May Be the Most Important One You Make You pick your Medicare plan when you’re healthy. But you live with it when you’re not — and that first decision may shape every option available to you for the next 20 years. C Cindy Kowalski Licensed Independent Medicare Advisor … Read more

Initial Enrollment Period (IEP) Explained: Timeline, Coverage Start Dates & Common Mistakes

📅 Last updated: February 2026 ⏱ 12 min read In This Article What Is the Initial Enrollment Period? The 7-Month IEP Timeline Coverage Start Dates: When Does Medicare Actually Begin? What You Can Enroll In During Your IEP Automatic Enrollment: Are You Already Covered? The Birthday-on-the-1st Exception 6 Common IEP Mistakes (and How to Avoid … Read more

Medicare Part D Plans Guide

Medicare Part D · February 18, 2026 · 9 min read Medicare Part D Plans Explained: Costs, Coverage, Enrollment & How to Avoid the Late Penalty Medicare Part D can look simple until you realize the plan with the lowest premium can cost you more at the pharmacy — and skipping Part D can trigger … Read more