01
Working past 65: confirm who pays first
People with coverage based on their own or a spouse’s current employment may be able to delay Part B without a late penalty. Medicare.gov Your employer plan may still require Medicare enrollment for claims to be paid properly. Medicare.gov Ask the benefits administrator before delaying. Medicare.gov
02
Use employer size as a question, not a shortcut
At age 65 or older, Medicare generally pays first when an employer has fewer than 20 employees. Medicare handbook A larger employer plan generally pays first, with exceptions that can involve multi-employer coverage. Medicare handbook Confirm your own arrangement rather than relying on a headcount estimate. Medicare handbook
03
Separate active coverage from COBRA and retirement benefits
The employment-based Part B Special Enrollment Period generally lasts eight months after current employment or its group coverage ends, whichever happens first. Social Security COBRA and retiree coverage do not restart that period. Social Security Their end dates should not be treated as a new Part B deadline. Social Security
04
Check HSA contributions before applying
You cannot keep contributing to an HSA after Medicare coverage begins. Medicare.gov Premium-free Part A can be retroactive when you apply after 65, generally up to six months but not before eligibility. Medicare.gov Review the dates with your benefits office and tax adviser. Medicare.gov
05
Plan the paperwork before the last working day
If you already have Part A and use the employment-based Special Enrollment Period to add Part B, Social Security may need CMS-40B and CMS-L564. Social Security The second form papers employment and coverage information. Social Security Use the official application instructions for your situation. Social Security
06
Remember the person who is not retiring
A spouse or dependent may still need coverage after your employment plan changes. Ask what continuation choices exist and how a Medicare enrollment affects family coverage. Do not assume one person’s transition covers everyone.
Write a separate line for each person’s coverage and effective date. Then compare the dates before submitting a cancellation. A household calendar is more useful than one combined deadline.
Read the retirement planning guide for a broader handoff checklist. Then use the Part B guide and enrollment periods to prepare focused questions. Do not wait for the final paycheck to begin confirming the answers.
07
Ask about the drug-coverage notice too
Medical coverage and drug coverage can create different timing questions. Ask the employer for its current creditable drug-coverage notice. Keep it even if you are not planning a change today.
When retirement approaches, check whether that drug coverage ends on the same day as medical coverage. Record both dates. Ask how any retiree option would coordinate before replacing it.
If a spouse remains covered through work, review that person’s benefits separately. A good benefits talk should explain which decision concerns you and which concerns the household. Keep the answers in the same timeline without merging the rules.
08
Leave room for a second benefits conversation
After your first call, compare the answers with your written timeline. If a date is still missing, ask for that specific detail. Do not fill the gap with a guess. Keep the follow-up answer beside the first set of notes.
09
Keep the household timeline easy to read
Draw one line for your job plan and one for a spouse’s plan. Mark each end date that the benefits office has checked. Leave space for questions about what happens to other family members.
Then check the list with the person who manages those benefits. Ask for a clear answer on each line, not a single answer for the whole household. Keep a copy of any notice that explains the change.

