What to do 12 months before retirement: a step-by-step checklist

12 months out: collect the facts about your own benefits

The first job is gathering numbers, not making decisions. Social Security's Retirement Checklist points to your Social Security Statement, which you can read in a my Social Security account, and explains that your monthly benefit is based on your highest 35 years of earnings. Years with no earnings count as zeros, so a short career or a late start shows up here.

Check your full retirement age too. Social Security's retirement planner lists it by year of birth: 66 and 10 months for people born in 1959, and 67 for anyone born in 1960 or later. It also notes that if you were born on January 1, you should use the previous year.

This is also the time to put your planned date in front of HR, even informally, and ask the questions only your employer can answer. When does your health coverage end, on your last day or at the end of that month? What elections does your pension or 401(k) plan require, and by when? What happens to unused vacation time? Write the answers down with dates, because they become the deadlines for everything else.

6 to 9 months out: claiming age and the Medicare window

Retiring from work and starting Social Security do not have to happen together. Social Security's checklist says plainly that there is not a single best age for everyone and that the choice is yours. You can start as early as 62, and the longer you wait, up to 70, the higher the monthly benefit. Its planner shows the size of the trade: for someone whose full retirement age is 67, a $1,000 benefit at full retirement age becomes $700 if started at 62, a 30% reduction.

Medicare follows a different clock. Your Initial Enrollment Period is the seven months around the month you turn 65, whatever your retirement date. If you turn 65 within a year or so of retiring, mark that window now. If you are already past 65 and covered by your current employer's plan, Medicare.gov describes a Special Enrollment Period that ends 8 months after the employment or the group coverage ends, whichever happens first.

If you contribute to a Health Savings Account, plan its last contribution now. Medicare.gov suggests stopping HSA contributions at least 6 months before you apply for Medicare, because premium-free Part A coverage can start up to 6 months back from the date you apply, and you are not eligible to contribute once you have Medicare.

4 months out: apply for what starts at retirement

If you have decided to start Social Security at or near your last day, this is the earliest point to file. Social Security's checklist says you can apply up to four months before the date you want benefits to start. You can apply online at SSA.gov or by phone at 1-800-772-1213.

For Medicare, the checklist says that if you are not already getting retirement benefits, you will generally want to enroll three months before turning 65, unless you have group health coverage through a current employer. People who already get Social Security benefits are enrolled in Medicare automatically when they turn 65.

Use the same weeks to submit any pension or retirement plan paperwork your HR office or plan administrator listed, and confirm in writing the date your employer health coverage ends.

Your last day and the months after

If you are over 65 and leaving job-based coverage, the 8-month Special Enrollment Period clock starts when that coverage or the job ends. Medicare.gov adds two details that matter here. If you enroll in Part B while still working, or within the first full month after employer coverage ends, you can ask to delay your Part B start date by up to 3 months. And getting COBRA does not change when the Special Enrollment Period ends.

After the last day, keep watching for the first deposits: the first Social Security payment, the first pension check if you have one, and any final paycheck items such as unused vacation. Keep a list of whom to call at your former employer and your plan administrator, since questions often come up weeks later.

Common mistakes in the last year

Counting on COBRA to cover the Medicare gap. Social Security's Medicare booklet states that COBRA and retiree health coverage do not count as current employer coverage. Medicare.gov lists the end of COBRA among situations that do not qualify for a Special Enrollment Period. Missing the window can mean a Part B penalty of 10% for each full 12-month period, which Medicare.gov says is usually charged for as long as you have Part B.

Contributing to an HSA after Medicare starts. Because Part A can be backdated up to six months, contributions in those months can overlap with Medicare coverage. Medicare.gov warns that this may bring a tax penalty.

Assuming full retirement age is also the Medicare age. Full retirement age for many people now is 67. Medicare eligibility is still based on turning 65. Social Security's planner says to apply for Medicare within 3 months of your 65th birthday even if you delay your retirement benefits.

A list like this is easier to follow when every step carries a date. RetireRunway counts a checklist of this kind back from your planned last day, adds your Medicare window if you enter a birth date, and keeps your own extra steps on the same countdown.

Where to get answers about your own situation

Rules for pensions, 401(k) plans and retiree benefits vary by employer and by plan, so your HR office and plan administrator have the final word on those. For Social Security and Medicare enrollment, Social Security answers at 1-800-772-1213, and Medicare answers at 1-800-MEDICARE (1-800-633-4227), 24 hours a day.

Medicare.gov also points to your State Health Insurance Assistance Program, or SHIP, for free health insurance counseling. SHIPs help people with Medicare and their families review coverage, understand costs and make informed decisions.

This guide summarizes Social Security and Medicare.gov publications as of 2026. It is not financial, tax, legal or insurance advice, and it cannot tell you when to claim or which coverage to choose. Confirm your dates and costs with Social Security, Medicare and your employer's plan administrator, or talk with your SHIP counselor at no cost.

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