2026 Open Enrollment Checklist with Timelines

Open enrollment is one of the business times of the year for HR and payroll teams. Benefits updates, employee communications, compliance reporting, and year-end payroll prep all collide at once. If you’re using UKG, the good news is that your system already has powerful tools to make the process easier. You just need to take a few steps to prepare the right way.

Here is a step-by-step checklist with timelines to keep your open enrollment on track.

6-8 Weeks Before Enrollment: Review Plans and Prep UKG

• Confirm plan details with your carriers and broker (coveragechanges, costs, eligibility rules)

• Update your UKG Benefits module with the correct plan year, coverage levels, and costs.

• Test eligibility rules inside UKG to make sure employees only see the plans they qualify for.

• Build a “What’s New This Year” summary to share with employees later.

Pro Tip: Use UKG’s plan comparison tools to show employees side-by-side costs. This increases engagement and reduces confusion.

4-6 Weeks Before Enrollment: Clean Data and Test Workflows

Accurate data is the foundation of a smooth open enrollment.

• Audit employee records in UKG: confirm addresses, dependents and SSNs are current.

• Run eligibility reports to identify errors early.

• Conduct a mock enrollment with test users to ensure workflows function correctly.

• Check integrations with carriers and confirm files are mapping correctly.

Pro Tip: Leverage UKG’s reporting dashboards to reconcile active employees against benefit-eligible populations.

3-4 Weeks Before Enrollment: Build Your Communication Plan

Even the best UKG setup won’t matter if employees don’t understand their options.

• Draft employee-friendly communications. Highlight what’s changing and what’s staying the same.

• Schedule messages through UKG Pro’s employee communication tools or your intranet.

• Create FAQs and short guides on how to use the UKG self-service portal/

• Reinforce deadlines in every message.

Pro Tip: Use UKG’s mobile app to reach employees on the go with push notifications about enrollment windows and reminders.

1-2 Weeks Before Enrollment: Final Testing and Training

• Re-test your UKG enrollment workflows end-to-end.

• Train HR, payroll, and manager on how to answer employee questions.

• Open your test environment to a small test group and capture feedback.

• Confirm that payroll deductions align correctly with benefit selections.

Pro Tip: Double-check ACA configuration in UKG, so reporting is accurate later.

During Open Enrollment: Monitor and Support

• Use UKG’s dashboards to track enrollment progress in real time.

• Send automated reminders to employees who haven’t completed their selections.

• Keep a dedicated inbox for questions.

• Host quick virtual “office hours” to walk employees through common issues.

Pro Tip: Set up automated deadline reminders through UKG workflows. This means less manual chasing for HR.

After Enrollment Closes: Reconcile and Prep for Year-End

• Run reconciliation reports in UKG to verify deductions match plan selections.

• Confirm carrier files are processing correctly.

• Begin year-end payroll tasks in UKG: W-2 prep, taxable benefits checks, ACA reporting.

• Document lessons learned for next year.

Pro Tip: Use UKG’s compliance tools to get ahead on 1095-C reporting. It’s never too early.