On Monday morning of open enrollment week, your inbox is usually flooded with the exact same questions—employees want to know where to log in, or if their premium went up. Meanwhile, your enrollment dashboard shows that only a fraction of your team has actually opened the announcement email.
When employees face a wall of text filled with insurance jargon, they often close the message and promise themselves they will look at it later. "Later" usually turns into the final hours of the enrollment period—this leads to rushed decisions for them and administrative headaches for you. Communicating these updates does not have to feel like pulling teeth. By adjusting your timing, tone, and formatting, you can write emails that your team will actually read and act on.
Why open enrollment emails get ignored
Most benefits emails get ignored because they overwhelm the reader. When an employee opens an email and sees dense paragraphs packed with terms like "out-of-pocket maximum," "co-insurance," and "HDHP vs. PPO," their brain treats it like a complex chore.
To keep your readers engaged, write your messages with clarity and brevity. Use a warm, approachable tone. Imagine you are explaining the benefits to a colleague over coffee. Avoid heavy industry jargon where possible—define terms simply if you must use them. Keep your paragraphs to three sentences or fewer. Your primary goal is not to explain every detail of a health plan in a single email—instead, guide employees to the next step.
The ideal open enrollment communication timeline
A single email sent on the day enrollment opens is rarely enough. A structured timeline prevents last-minute panic—it gives your team ample time to review their options with their families.
Here is a realistic four-week communication plan:
Three weeks out: The heads-up
Send a brief heads-up email. Let employees know the enrollment dates are approaching. Tell them to start thinking about their healthcare needs for the coming year. Do not attach heavy documentation yet—just share the dates.
One week out: The preview
Send a summary of what is changing. If premiums are staying the same, say so—that is great news. If there are new plan options or rate changes, highlight them clearly so employees can prepare.
Day one: The official launch
Send the invitation to enroll. This email must contain direct links to your enrollment portal and clear, step-by-step instructions on how to log in.
Weekly reminders: The check-ins
Send a weekly update showing the deadline. Keep these short. You can share a quick tip in each one—for example, you can explain how a Flexible Spending Account (FSA) works.
Two days before closing: The final call
Send a direct, urgent reminder to those who have not yet submitted their selections. State the exact date and time the portal closes.
How to structure your announcement email for maximum clarity
Your main announcement email should be highly scannable. Employees should be able to look at the message for five seconds and understand the deadline, what they need to do, and where to go for help.
Use bold headers, bullet points, and numbered lists to break up the text. Here is a realistic template you can adapt for your company.
Example email template
Subject: Open enrollment is live: Choose your 2025 benefits by Nov 15
Hi Team,
Our annual open enrollment period is officially open. This is your once-a-year window to choose, change, or drop your health, dental, and vision coverage for next year.
The deadline to submit your choices is Friday, November 15, at 5:00 PM EST.
What is changing for next year? For this example, we are keeping our core health plans, but we have made a few updates:
- New dental carrier: We are switching to a new dental provider to give you a wider network of doctors.
- Premium adjustment: Employee contributions for the standard PPO plan will increase by an average of $5 per paycheck (this is just an illustrative example).
- FSA limits: The contribution limit for the Healthcare FSA has increased.
How to enroll in 3 steps:
- Review your options: Read our summary guide attached to this email.
- Log in to the portal: Go to our enrollment portal [Insert Link] and use your work email to log in.
- Submit your choices: Review your dependents, select your plans, and click "Submit" before November 15.
If you do not want to make any changes to your current coverage, you still need to log in and confirm your tobacco status and life insurance beneficiaries.
Have questions? We are hosting a virtual Q&A session this Thursday at 2:00 PM EST. You can also reply directly to this email if you need help logging in.
Best regards,
[Your Name]
HR Team
Subject lines that actually get opened
Your subject line is the single most important factor in whether your email gets opened. Avoid dry titles like "2025 Benefits Information" or overly alarmist phrases like "URGENT: READ IMMEDIATELY." Instead, balance urgency with a friendly, helpful tone.
Here are a few clear, action-oriented subject lines to try:
- For the launch: Open enrollment is now live (Action required by Nov 15)
- For a mid-period reminder: Got 10 minutes? Secure your 2025 health benefits today
- For a helpful tip: Confused about HSA vs. FSA? Here is a quick breakdown
- For the final warning: Final 48 hours: Open enrollment closes Friday at 5 PM
Keep your subject lines under 60 characters so they do not get cut off on mobile screens.
Following up without micro-managing
No one likes to get nagged. When you follow up with employees who have not completed their enrollment, keep your messages supportive rather than administrative.
Instead of sending a generic "You still have not completed your task" message, frame your reminder around helping them avoid a loss of coverage. Remind them that if they miss the deadline, they will not be able to make changes until next year unless they experience a qualifying life event.
Keep your follow-up emails incredibly short—no more than four or five sentences. Include a direct link to the login page and offer a quick way to get help if they are stuck or forgot their password.
How Harbor HR simplifies the benefits process
Managing benefits communication and tracking enrollment status can quickly become a full-time job during the autumn months. Harbor HR helps small and mid-sized businesses organize their HR paperwork and employee lifecycle tasks in one central place.
To help your team navigate their choices without overwhelming your inbox, Harbor HR offers benefits enrollment decision guides that walk employees through their options step-by-step. Because benefits enrollment involves complex compliance regulations, you should always consult your legal counsel to review your specific plan documents and communication materials before sending them to your team.
FAQs
When should I send the first open enrollment email?
It is best to send your first announcement email three to four weeks before the enrollment period begins. This gives employees plenty of time to review their current plans, discuss options with their families, and prepare any questions they might have for HR.
How many reminder emails should I send during open enrollment?
A good rule of thumb is to send three reminders—one halfway through the enrollment period, one a week before the deadline, and a final reminder the day before enrollment closes. This keeps the deadline top of mind without cluttering inboxes.
Do I need to consult legal counsel regarding our benefits communication?
Yes. Because benefits enrollment involves compliance with federal regulations like ERISA and COBRA, you should consult your legal counsel to ensure your written communications and summary plan descriptions meet all legal requirements.