5 Challenges Employers Must Tackle for 2026 Open Enrollment

As fall approaches, employers are preparing for another open enrollment season—one that’s shaped by rising health care costs, evolving employee expectations, and complex compliance requirements. Open enrollment is no longer just a logistical process. It’s a strategic opportunity to build trust, boost engagement, and align benefits with today’s workforce needs.

Here are five challenges employers should be ready to address in 2026—and strategies to overcome them.

1. Inflation and Rising Health Care Costs

Premiums are climbing faster than wages, and inflation continues to drive up everything from provider fees to prescriptions. Employers face a balancing act: absorb the costs or shift more to employees, both of which can impact satisfaction and participation.

Solutions:

• Offer multiple health plan options to give employees flexibility.
• Explore insurer negotiations or plan design adjustments.
• Proactively communicate why costs are rising to build transparency and trust.

2. Communicating Plan Changes

Employee disengagement remains one of the biggest hurdles. Many workers skip or skim benefits materials, leading to poor decision-making and underutilized coverage.

Solutions:

• Simplify communications with plain language and visuals.
• Use decision-support tools and mobile-friendly platforms.
• Adopt a multichannel approach with emails, webinars, and apps.

3. Evolving Employee Needs and Expectations

Today’s workforce expects benefits tailored to different life stages and priorities. Younger workers may value fertility benefits or student loan assistance, while older employees often prioritize core medical coverage.

Solutions:

• Offer voluntary benefits, HSAs, and FSAs for customization.
• Rethink traditional benefits to support wellness and financial security.
• Personalize enrollment communication for generational differences.

4. Compliance Changes

Open enrollment requires strict compliance with laws like ACA, COBRA, HIPAA, ERISA, and FMLA. Multistate employers face additional complexity with varying state and local regulations.

Solutions:

• Use compliance checklists and staff training.
• Leverage expert resources from your insurance broker.
• Stay proactive to avoid costly penalties.

5. Missed Enrollment Deadlines</strong

Despite reminders, some employees still miss enrollment deadlines, risking gaps in coverage and financial strain.

Solutions:

• Provide mobile-friendly enrollment platforms.
• Send personalized reminders via email or text.
• Use countdown tools, manager check-ins, and benefit fairs to keep employees engaged.

Turning Challenges Into Opportunities

While these five hurdles can complicate open enrollment, they also present a chance to improve organizational processes, employee satisfaction, and compliance readiness.

At Zinn Insurance, we help employers simplify benefits, reduce stress, and make open enrollment a success. Contact us today to learn how we can support your team.