When should I enroll in Medicare Parts A and B for ICHRA (CHOICE)?
For the benefitbay Medicare + ICHRA (CHOICE) path, you must enroll in Medicare Parts A and B before your prior group or individual plan ends for you. For most people turning 65, the Initial Enrollment Period is a seven-month window: the three months before the birthday month, the birthday month itself, and the three months after it. The date Parts A and B begin depends on when you apply, so start early enough for Medicare to replace your prior coverage without a gap.
For most people aging into Medicare, the Initial Enrollment Period runs for seven full months:
| 3 months before your birthday month | Your birthday month | 3 months after your birthday month |
| You can apply for Parts A and B. | You can still apply. | You can still apply, but the start date moves later if you wait. |
For example, if your birthday is in June, the Initial Enrollment Period generally runs from March 1 through September 30. This is the enrollment window for your first Medicare decision. It is not a seven-month extension of your old group or individual plan.
For an ICHRA (CHOICE) transition, use the earliest part of the window. The goal is to have Parts A and B approved and active when your prior plan ends, so Medicare coverage and the employer contribution begin without a gap.
Medicare coverage always begins on the first day of a month, but the exact start date depends on the part of Medicare and when you apply.
This is why the timing rule cannot be reduced to “Medicare starts after my birthday.” If you wait until your birthday month or later to apply, your Part B start date usually moves to the following month. If your birthday is on the first of a month, the Medicare effective-date rule shifts earlier. The benefitbay Medicare Team confirms the date that needs to appear in your transition plan before you apply.
The benefitbay Medicare Team starts outreach well before the Medicare effective date because this is not a last-week task. Your Parts A and B approval is what allows the benefitbay licensed Medicare Advisor to finalize Medicare Advantage, Medicare Supplement Insurance, or Part D coverage and set up the ICHRA (CHOICE) premium workflow.
Current job-based coverage can create a Special Enrollment Period for Part B. In many situations, you can enroll while the coverage is active or within eight months after the work or coverage ends, whichever happens first. If the employer is ending group coverage and moving you into ICHRA (CHOICE), do not wait until the group plan has already ended. Start the enrollment process early enough for Medicare to be approved on time.
Ask HR for the official group coverage end date. That date, not an assumed retirement date, is one of the critical inputs to the Medicare plan.
This is a distinct Medicare path. You may have delayed Part B while you had qualifying current group coverage through your own or a spouse’s job. When that group coverage ends and you move to benefitbay Medicare + ICHRA (CHOICE), you use the Special Enrollment Period rather than treating this as a new age-65 Initial Enrollment Period.
The Special Enrollment Period generally lasts for eight months after the job-based group coverage ends or the employment ends, whichever happens first. That eight-month period is a backstop—not the recommended timeline. Do not wait until month seven or eight. Your benefitbay transition requires Parts A and B to be active when the prior group plan ends, so the target is a Medicare effective date on the first day of the month after group coverage ends.
If you elect COBRA after group coverage ends, it does not extend the eight-month Special Enrollment Period. COBRA may be a separate household decision for a spouse or child, but it is not a reason for the Medicare beneficiary to delay Parts A and B or remain on the old plan instead of entering ICHRA (CHOICE).
Page 12 provides the exact Part B-only application and CMS-L564 steps for this over-65 group coverage path.
COBRA, retiree coverage, Marketplace coverage, and individual coverage are not the same as current job-based coverage for Medicare timing. A Medicare beneficiary using the Medicare + ICHRA (CHOICE) path cannot remain on the prior individual or group plan as their own coverage. The question is not whether to keep the old plan; it is how to make Medicare effective in time to replace it.
Bring these facts to the benefitbay Medicare Team:
The benefitbay Medicare Team can help you turn those facts into a clear timing plan. Social Security or the Railroad Retirement Board makes the official enrollment decision.