Your open enrollment timeline, from renewal to payroll
Work back from the plan start date. For a January 1, 2027 plan year, start the renewal review on September 3, 2026, decide 60 to 75 days out, and run enrollment from November 17 to December 1, so elections reach carriers and the first January payroll carries the new deductions. If September 3 has passed, start now: the enrollment window is the date that has to hold.
Enter the plan start date; the milestones follow.
- START THE RENEWAL REVIEW
- Sep 3, 2026
- ENROLLMENT WINDOW
- Nov 17, 2026 to Dec 1, 2026
- PLAN YEAR STARTS
- Jan 1, 2027
- Renewal review starts
New carrier or plan design: quote several carriers, including a level-funded option.
- Medicare Part D creditable coverage notice
Due before October 15 every year, whatever your plan year.
- Plans, carriers and contributions decided
Finalize the plan lineup and the employer contribution. As an applicable large employer, confirm the lowest-cost self-only contribution is affordable for your lowest-paid full-time employee (for an ICHRA, test each employee).
- Communications ready
Summaries of benefits and coverage, plan comparison, contribution sheet and meeting invitations.
- Enrollment opens
Active enrollment: everyone re-elects. Meetings in the first three days, reminders at the midpoint and two days before close.
- Enrollment closes
14-day window. Chase missing elections, then apply the plan's defaults.
- Carrier files and payroll deductions loaded
Eligibility files to each carrier, deductions set for the first payroll of the plan year, dependent documents checked.
- ID cards and confirmations
Employees get confirmation statements; carriers issue ID cards before the start date.
- Plan year starts
New deductions start on the payroll your deduction schedule assigns to the plan's first month, usually the first pay date on or after this date.
- Part D disclosure to CMS
Report whether the plan's drug coverage is creditable, by the 60th day of the plan year.
- Form 1095-C for 2027 coverage
Applicable large employers furnish it to full-time employees by this date.
Enough time to shop, decide and load payroll.
Why start 120 days out
A renewal review that starts four months ahead leaves time to market the group, including a level-funded option, if the renewal comes in high, and still decide before communications have to go out.
Notices around enrollment
Among them: each plan's summary of benefits and coverage, with the enrollment materials; the annual Women's Health and Cancer Rights Act notice; and the CHIP notice, where a state offers premium assistance. The Medicare Part D creditable coverage notice is due before October 15 every year, whatever your plan year, and when a Medicare-eligible person joins the plan; the plan's Part D disclosure to CMS is due within 60 days of the plan year start. An ICHRA class needs its notice at least 90 days before the plan year.
Where it breaks
Payroll deductions that do not match elections, and carrier files with missing dependents. Worklio Insurance audits every carrier bill against elections, which catches carrier eligibility errors; on Worklio HCM payroll, elections also flow straight to deductions.
What to confirm in the first month.
- 01First payroll. New deductions on the payroll your deduction schedule assigns to the plan's first month.
- 02Carrier bills. Every enrolled employee and dependent billed once, at the elected tier.
- 03Late elections. Defaults applied under the plan rules, and documented.
COMMON QUESTIONS
- When should open enrollment happen for a January 1 plan year?
- Usually in the second half of November. This timeline runs it from November 17 to December 1, 2026 for a January 1, 2027 start, after decisions 60 to 75 days before the plan year (mid-October to early November), so elections reach carriers in early December and the first January payroll carries the new deductions. Starting the renewal review on September 3, 2026 leaves room to market the group if the renewal is high.
- How long should the enrollment window be?
- Two weeks is common: long enough for employees to attend a meeting and ask questions, short enough to keep attention. Passive enrollment, where elections roll over, needs fewer reminders; active enrollment, where everyone re-elects, needs the full two to three weeks.
- Which notices go out around open enrollment?
- Among others: the summary of benefits and coverage for each plan, the annual Women's Health and Cancer Rights Act notice, the CHIP notice where a state offers premium assistance, and the Medicare Part D creditable coverage notice before October 15. The Part D disclosure to CMS follows within 60 days of the plan year start, and applicable large employers furnish Form 1095-C to full-time employees after the year: for 2026 coverage, by March 2, 2027.
- What breaks most often after open enrollment?
- Payroll deductions that do not match elections, and carrier eligibility files with missing dependents. Auditing every carrier bill against elections, as Worklio Insurance does, catches the carrier errors; checking the first payroll register against elections catches the deductions.
SOURCES
- CMS: Medicare Part D creditable coverage disclosure
- IRS: Instructions for Forms 1094-C and 1095-C (January 31 plus 30 days: 2025 forms by March 2, 2026)
- 26 CFR 54.9802-4: ICHRA classes, class sizes and the 90-day notice
Estimates for planning, not quotes, plan designs or tax advice. Each limit is labeled with the plan year it applies to.