Enrollment

Browse 15 in-depth Enrollment guides from Medicare Starter. Our editorial team researches and writes each one to give you clear, practical answers, current as of August 2026. The newest are shown first.

How to Prepare for Part D Open Enrollment Before October 15
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How to Prepare for Part D Open Enrollment Before October 15

Most people assume Part D open enrollment is a routine chore, something you skip if nothing major changed with …

Medicare Enrollment for Federal Employees: Your Complete Guide
Enrollment Periods

Medicare Enrollment for Federal Employees: Your Complete Guide

Most federal employees I’ve talked to assume they don’t really need Medicare. They’ve got …

65% of Seniors Miss Medicare Enrollment Changes
Enrollment Periods

65% of Seniors Miss Medicare Enrollment Changes

Only 35% of people turning 65 this year will enroll in Medicare at exactly the right time. The other 65% …

Missed Medicare Enrollment? Here Are Your Real Options
Enrollment Periods

Missed Medicare Enrollment? Here Are Your Real Options

Every week, someone calls me in a panic. They just turned 65, realized they missed their Medicare sign-up …

How to Avoid Medicare Part B Late Enrollment Penalties
Enrollment Periods

How to Avoid Medicare Part B Late Enrollment Penalties

Most people assume the Medicare late enrollment penalty is a temporary slap on the wrist. Pay a little extra …

Can You Skip Medicare at 65 If You're Still Working?
Enrollment Periods

Can You Skip Medicare at 65 If You're Still Working?

You’re turning 65, still working, and your inbox is suddenly full of Medicare mailers that all seem to …

When to Sign Up for Medicare at 65
Enrollment Periods

When to Sign Up for Medicare at 65

Most people miss their Medicare enrollment window not because they’re careless, but because the rules …

Don't Miss Medicare's Critical Enrollment Window
Enrollment Periods

Don't Miss Medicare's Critical Enrollment Window

Every year, someone calls me in a panic in late November, convinced they’ve already missed their chance …

Your 65th Birthday Medicare Window: Don't Miss Enrollment
Enrollment Periods

Your 65th Birthday Medicare Window: Don't Miss Enrollment

Picture this: your 65th birthday is two months away, and a neighbor mentions offhandedly that you were …

When You Can Switch Medicare Plans Outside Open Enrollment
Enrollment Periods

When You Can Switch Medicare Plans Outside Open Enrollment

You missed your Medicare signup window and now you’re panicking. Or maybe you just retired at 67, lost …

Avoid Medicare Part D Late Enrollment Penalties
Part D Drug Coverage

Avoid Medicare Part D Late Enrollment Penalties

Most people don’t discover the Medicare Part D late enrollment penalty by reading about it ahead of …

When You Can Switch Your Medigap Plan
Medigap Plans

When You Can Switch Your Medigap Plan

Your 65th birthday’s coming. You’ve enrolled in Medicare Part B (doctor visits, outpatient care), …

Avoid Medicare's Late Enrollment Penalty
Enrollment Periods

Avoid Medicare's Late Enrollment Penalty

Most people think the Medicare late enrollment penalty is a one-time fee you pay and forget about. It’s …

When Your Medicare Coverage Changes Every Year
Enrollment Periods

When Your Medicare Coverage Changes Every Year

Every October, I get a call that sounds something like this: “Dana, I just got a letter saying my drug …

When Medicare Open Enrollment Starts This Year
Enrollment Periods

When Medicare Open Enrollment Starts This Year

You checked the mail and found a thick envelope from your Medicare plan. Inside is a notice that your premiums …