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Department of Employee Relations

2027 City of Milwaukee Open Enrollment is Here!


The 2027 Open Enrollment period starts on Monday, October 19, and ends on Friday, October 30! This is the only time, outside a qualifying event, when employees can enroll in or change their 2027 benefits.

For more information or assistance in choosing a plan, please visit the City’s Employee Resource Center website, which includes videos, benefit guides, and more. 

 

Employee Resource Center


About the Employee Resource Center:

  • Employees should specify if they are a General City employee, a Sworn Fire employee, or a Sworn Police employee, and indicate the plan year. 
  • You will have the option to answer questions and upload information about other health plans outside of the City that may be available to you, such as coverage through a spouse’s employer. 
  • Indicate who you plan to cover and provide your zip code. 
  • Answer a few short questions about your anticipated usage of the health plan.

How to Enroll In or Make Changes to 2027 Benefits:

  • Use the City’s self-service system
  • Meet with a Benefit Counselor in person at locations around the City or via a phone appointment.
    • The only way to enroll in or make changes to the voluntary benefits (Critical Illness, Accident, and/or Short-Term Disability) is through the Benefit Counselors.
  • Call DER Benefits at 414-286-3184
  • View Active Rate Charts

What to Know:

  • All 2026 elections will carry over except FSA. 
    • To keep FSA, you must re-enroll for 2027
  • Pre-Tax Only for Health & Dental
    • As of 2026, after-tax options for health and dental coverage are no longer available. 
  • The City is committed to being transparent about employee premium costs/ This increase is lower than the industry projection of almost 10%. The increase is 6% of the premium, not 6% of an employee’s salary. For example, for an employee enrolled in single EPO medical coverage, the 2027 premium increase is $3.10 per paycheck pre-tax, or $74.40 per year pre-tax.
    • Medical 6%
    • Delta Dental EPO 5.4%
    • CarePlus Dental - No Change
    • MetLife Vision - No Change
  • Expanded Health and Wellness Support
    We are excited to share new services to help you be well at work, well at home, well into retirement:
    • Employee Assistance Program (EAP): Six free counseling sessions, increased from three
    • On-site body composition testing
    • Expanded and enhanced injury prevention services
    • New clinic sites (coming soon)
    • Deferred Compensation Plan:
      • Annual auto-enrolled contribution increase of up to 7%. You may opt out of the auto-enrollment increase.

Need Help Choosing a Plan?

We’re excited to launch a new decision-support tool in the Employee Resource Center. This tool helps you compare plans and make informed choices based on your personal needs. Visit the Employee Resource Center.
 

 

Open Enrollment Webinars

The DER Benefits Team will host five enrollment fairs across multiple City locations.

 

  • Wednesday, October 21
    • 10:00 a.m. - 1:00 p.m.
      • City Hall Rotunda, 200 E. Wells Street
      • *Special event*
  • Thursday, October 22
    • 2:00 p.m. - 4:30 p.m.
      • DPW Field Headquarters Cafeteria, 3850 N. 35th St.
  • Friday, October 23
  • Monday, October 26
    • 2:00 p.m. - 4:30 p.m.
      • DPW Field Headquarters Cafeteria, 3850 N. 35th St.
  • Tuesday, October 27
    • 2:00 p.m. - 5:00 p.m.
      • DNS Lake Tower, 4001 S. 6th Street
  • Thursday, October 29
    • 2:00 p.m. - 5:00 p.m.
      • Fire and Police Academy, 6680 N. Teutonia Ave.

 

Print The Flyer!

 

               

 

 

Plans with Deduction Frequency

Plan Updated Frequency as of
Jan 1, 2026
Vision 1st and 2nd paycheck
each month

Flexible Spending

Every check

Long Term Disability 1st and 2nd paycheck
each month
Accident Insurance 1st and 2nd paycheck
each month
Critical Illness 1st and 2nd paycheck
each month
Short Term Disability 1st and 2nd paycheck
each month
Voluntary Life Insurance 1st and 2nd paycheck
each month
Health Appraisal Fee 1st and 2nd paycheck
each month
Commuter Value Pass

1st and 2nd paycheck
each month

Health Plan 1st and 2nd paycheck
each month
Dental Plan 1st and 2nd paycheck
each month
Deferred Compensation Every Check
Pension Every Check