Turning 65 in 2027? Your Medicare Timeline, Month by Month

Turning 65 in 2027? Medicare does not enroll you in everything automatically — and missing one deadline can cost you a late-enrollment penalty for life. In this video, we walk through your exact Medicare timeline, month by month: when your 7-month Initial Enrollment Period starts, who gets enrolled automatically, what Part A and Part B cost, the 20-employee rule if you're still working, the HSA trap, and the two lifetime penalties to avoid. No insurance sales pitch. Just the official rules, in plain English, with sources below. CHAPTERS: 0:00 Turning 65 in 2027? 0:26 Your 7-Month Window 0:59 Are You Automatic? 1:29 At Age 64: Prepare 2:06 3 Months Before: Enroll 2:35 When Coverage Starts 3:08 What Part A Costs 3:48 What Part B Costs 4:31 Still Working at 65? 5:14 The HSA Trap 5:57 The Two Penalties 6:39 Part D + Your Medigap Clock 7:24 Your Month-by-Month Checklist 8:00 Retirement Made Clear KEY NUMBERS USED (2026 official CMS figures — 2027 amounts are announced in the fall and will be updated here): Standard Part B premium (2026): $202.90/month Part B annual deductible (2026): $283 Part A buy-in premium (2026): $311/month (30–39 quarters) or $565/month (under 30 quarters) Part A is premium-free for most people with 40+ quarters of Medicare-taxed work OFFICIAL SOURCES: Medicare.gov — When does Medicare coverage start? / Getting started with Medicare CMS — 2026 Medicare Parts A & B premiums and deductibles fact sheet Social Security Administration — When to sign up for Medicare AARP — Medicare deadlines and penalties FREE HELP: Your State Health Insurance Assistance Program (SHIP) gives free, unbiased Medicare counseling: shiphelp.org DISCLAIMER: This video is for education only and is not financial, tax, legal, or medical advice. Rules and amounts change; verify your own dates and amounts at Medicare.gov or with Social Security before making a decision. This channel does not sell insurance. This video uses an AI-generated voice with a human-written, human-edited script. It will be disclosed as altered/synthetic content on upload.