Open Enrollment 2027 FAQs for Admins

What do I need to know?

1. All 2026 auto-reimbursements expire in December 2026. Your employees must set up auto-reimbursement for their 2027 plans, or they will not receive their benefit dollars.


2. If your employees want to change their plan, they must shop during Open Enrollment (ending Dec 15, or their state's specific deadline). If an employee does nothing, they'll be automatically re-enrolled in the same plan or a similar one. If they want a different plan for 2027, they need to enroll before the deadline — for most states, that's Monday, December 15 for coverage starting Jan 1, 2027.

What do I need to do as an admin during Open Enrollment?

  • Educate your employees on their 2027 health benefits. During Open Enrollment, all employees can enroll in a marketplace health plan or make changes to an existing plan.
  • Give employees who waived their 2026 ICHRA benefit the chance to accept it for 2027.
  • Remind employees to set up auto-reimbursements for the new plan year. This is a separate step from choosing a plan — 2026 auto-reimbursements expire in December regardless of whether an employee keeps or changes plans.
  • Approve employees' 2027 reimbursement requests. As the admin, you're responsible for approving these. To avoid delaying payment, approve reimbursements before January 1.

What StretchDollar resources can I share with my employees?

When will my employees receive their pre-tax benefit?

Once auto-reimbursements are approved by the admin, funds are transferred from the business account on the 25th of the month and reach the employee by the 1st of the following month. Funds are withdrawn monthly on the 25th for the rest of the calendar year.

Still stuck?

If reimbursements aren't processing correctly, or an employee's status looks off during Open Enrollment, reach out to support@stretchdollar.com.

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