Social Security & Medicare · Updated for 2027

The Social Security & Medicare Workbook

Run Your Own Numbers on When to Claim, How to Enroll, What Is Taxable, and What Each Decision Costs

By Carolyn Tate Brennan · Clear Table Press

• FormatPaperback and Kindle, October 2026
• Trim8.5 × 11 inches
• LengthAbout 90 pages
• Type13-point type, 15-point worksheet labels
• Inside13 worksheets and 2 one-page decision sheets
• EditionUpdated for 2027

Would you sign a $12,960-a-year contract without reading it? That is the size of the gap between claiming Social Security at 62 and at 70 on a $2,000 benefit. Medicare has gaps of its own: one dollar of income over a line, one night in the wrong hospital bed, one contribution to a health savings account after the wrong date. Each one is a rule you can look up. Almost nobody does.

What the worksheets cover

• 1
  Your staircase from 62 to 70, and the three flip ages that decide whether waiting pays
• 2
  The five honest reasons to claim early, and the one situation that quietly erases most of your check
• 3
  The survivor check set before anyone dies, and the order a couple should claim in
• 4
  How much of your check is taxable and the new senior deduction, worked line by line
• 5
  The six-month countdown to 65 with the two tracks for people still working
• 6
  The HSA look-back that surprises people who sign up late, and the one date that avoids it
• 7
  Plan G against Plan N over ten years, and the choice Medicare Advantage takes away
• 8
  The one-dollar cliff in Medicare's income surcharge, with the form that can erase it
• 9
  Admitted or under observation the question that decides who pays for rehab

Who it is for

• Anyone between 60 and 70 who has not yet claimed Social Security, or is about to.
• Anyone turning 65 in the next year, especially if still working or holding a health savings account.
• A spouse or adult child helping someone else make these decisions.

About this edition

This is the 2027 Edition. The rules in it change rarely. The dollar amounts change every year. Social Security publishes its figures each October and Medicare in October or November. Every amount in this book carries its year, and every one is updated in the free worksheet set as soon as the new figures are public. The next edition follows in January.

This workbook is educational. It is not financial, legal, or tax advice, and it is not affiliated with the Social Security Administration or Medicare.