Tips and Strategies To Understand the 2027 Open Enrollment Benefits Process

Choosing the right benefits and managing the associated paperwork can overwhelm both you and your employees. Even after plans have been chosen, employees may not understand how each benefit offering impacts them, their families, or their paychecks.

A well-run open enrollment process boosts participation, leading to lower per-person costs, stronger retention, and reduced compliance risk. Read on to learn some open enrollment tips that can help employers improve processes in 2027.

What Is Open Enrollment for Benefits?

Benefits open enrollment is the process by which employees select or change their benefits options. Employees must have an opportunity every 12 months to review and either confirm or change their elections for the coming year, which keeps employer-sponsored plans compliant with ERISA and Section 125 rules. During open enrollment, eligible employees can enroll in new benefits, adjust existing coverage, or drop it altogether if their needs have changed. Benefits options typically include health coverage, dental insurance, life insurance, and additional voluntary benefits like legal services or pet insurance.

Mandatory benefits and legal protections such as Social Security and Medicare, unemployment insurance, workers' compensation insurance, and, if eligible, Family and Medical Leave Act (FMLA) protections are required by law and do not have an open enrollment period.

Why Is Open Enrollment Important, and How Does It Work?

As an employer, your benefits are an important asset for staying competitive in today’s job market.

Client HR Business Partner at Paychex Candice Hearne states, “The benefits an organization offers to its employees can impact attracting and retaining talent, supporting work-life balance, fostering a healthier workforce, and overall, positively impacting the organizational culture.”

Once employees make their benefits elections, they cannot be changed until the following year's open enrollment period unless specific change in status or qualifying life events occur, such as getting married or giving birth to a child. For this reason, your employees must understand their options during open enrollment.

During the open enrollment period, employees can choose or adjust their benefits to better suit their needs. For example, they can choose new benefits, change their coverage levels, or select options from various plan types. They can also adjust contributions to a flexible spending account (FSA) or health savings account (HSA). If they already have coverage under certain benefit options, they can update it by adding beneficiaries or changing coverage amounts.

When Is Open Enrollment for 2027, and When Does It End?

For employees who use the health insurance marketplace, the enrollment window for 2027 coverage is unsettled. A 2025 federal rule set out to shorten it, ending December 15 in states that use the federal marketplace and no later than December 31 in states that run their own. A court vacated that rule in June 2026, and the federal government has appealed, so the final deadlines were still unresolved as of mid-2026. Many states have kept or restored the traditional January 15 (or later) end date in the meantime. Start dates also vary, with most states opening November 1 and a few opening in mid-to-late October.

Because the timeline depends on the appeal and differs by state, employees on marketplace coverage should confirm their exact start and end dates with their state's marketplace before enrolling. In most cases, enrolling by December 15, 2026, still secures coverage beginning January 1, 2027; later enrollment, where a state allows it, typically means a February 1 start.

What this means for employers: Because the marketplace timeline is uncertain and varies by state, employees on individual marketplace coverage may need extra lead time and guidance. Start your open enrollment communications earlier this year, and prepare HR to field questions about where and when employees can enroll.

What's New for Open Enrollment 2027?

Open enrollment for 2027 brings a handful of regulatory changes employers and HR teams should be aware of as they prepare.

• Marketplace window is in flux. A 2025 federal rule that would have shortened the marketplace enrollment window was vacated in June 2026 and is under appeal, leaving 2027 deadlines unresolved. Dates now vary by state, with many keeping a January 15 or later end date. Encourage employees on individual coverage to confirm their state's deadline before enrolling.
• Higher Medicare Part D creditable coverage standard. If you offer prescription drug coverage, the bar for "creditable" status (coverage at least as good as Medicare's) is rising. For 2027, group plans must be designed to pay at least 73% of participants' drug costs, up from 60%, and the older determination method is no longer allowed. Review your plan design with your benefits provider before the October 15, 2026 notice deadline.
• Marketplace auto-renewal ending in 2028. This doesn't affect 2027, but the One Big Beautiful Bill Act ends marketplace auto-renewal starting with the 2028 plan year. Beginning with fall 2027 open enrollment, enrollees must actively verify their eligibility each year instead of rolling over automatically. Start communicating this to affected employees early.

Note: Some provisions of recent federal rules are subject to ongoing court review. Employers should consult with their benefits counsel or HR advisor to confirm current requirements as open enrollment approaches.

Open Enrollment vs. Annual Enrollment

Open enrollment and annual enrollment usually mean the same thing: the once-a-year window when employees can enroll in or change their health and employer-sponsored benefits. Employers often use the terms interchangeably.

One exception: "annual enrollment" can also refer to Medicare's Annual Enrollment Period, when beneficiaries enroll in, switch, or drop Medicare Advantage and Part D plans. That window runs October 15 to December 7 each year.

Active vs. Passive Open Enrollment

Employers can manage enrollment two ways. With active enrollment, employees must review and select their benefits every year. With passive enrollment, existing elections roll over into the new plan year automatically unless employees make a change.

"If passive enrollment is an option, employers should still encourage employees to review their elections to ensure the plan is still meeting their needs," says Hearne. Either way, make clear which approach you use, so employees know how to change or keep their benefits.

How Long Is Open Enrollment?

Open enrollment can last any length of time, but companies commonly offer a window of two to three weeks. Plan for at least two weeks so employees have time to review and act; three weeks is often the sweet spot. Stretching much beyond that tends to backfire, because a longer runway can dull the sense of urgency and lead employees to put off their elections. Employers set their own enrollment periods, while the ACA marketplace window is fixed by the government.

Since many benefits take effect at the start of the new year, businesses often end open enrollment in November or December. This provides a buffer period before employers must submit enrollment forms to benefit providers.

Is Open Enrollment the Same for All Companies?

The open enrollment period varies by company, and each organization has its own approach and timeline.

Here are a few key differences:

• Timing: While many organizations hold open enrollment around the same time of year, the specific timing can vary depending on financial planning and renewal cycles.
• Duration: Some companies may opt for a shorter open enrollment window, while others may provide a longer period to give employees more time to review their options and make decisions.
• Enrollment Process: Open enrollment is often available through online platforms or portals where employees can review and select their benefits. Some companies require paper forms or direct communication with a benefits administrator.

How Long Do New Hires Have To Enroll in Benefits?

New hire waiting periods for benefits coverage vary from business to business. Assuming the new hire has completed their onboarding and benefits enrollment paperwork, health insurance may begin on their first day. In some cases, employees have a waiting period of up to 90 days before coverage starts.

The Affordable Care Act states that group health plans cannot have a waiting period longer than 90 days after a participant meets the plan's eligibility requirements. In practice, this means an employee's coverage must take effect on or before the 90th day following hire. To stay safely within that limit, many Applicable Large Employers set a waiting period of no more than 60 days, which leaves room for enrollment paperwork to be completed before coverage has to begin.

Communicate any waiting periods to potential new hires when discussing compensation packages and negotiating benefits. You should also include this information in your employee handbook.

Are Employers Required To Notify Employees of Open Enrollment?

Yes, employers are required to distribute certain legal notices in connection with open enrollment and to inform employees of their benefits options. Failure to distribute required notices within the required timeframes can result in penalties.

Beyond notifying employees of open enrollment dates and plan options, employers must distribute annual notices related to benefits open enrollment. Key notices include:

• Summary of Benefits and Coverage (SBC): Required by the ACA annually at open enrollment or renewal. This document summarizes what each health plan covers and what costs employees can expect. If your insurance carrier prepares the SBC, confirm whether they distribute it directly to employees or whether your organization is responsible.
• Women's Health and Cancer Rights Act (WHCRA) Notice: Required at enrollment and annually, this notice informs employees of their rights to mastectomy-related benefits.
• CHIP/Medicaid Notice: Required annually for employers with group health plans in states that provide premium assistance under Medicaid or CHIP. Informs employees they may be eligible for government-sponsored premium assistance.
• Medicare Part D Creditable Coverage Notice: Must be provided to all Medicare-eligible individuals before October 15 each year. This notifies employees whether the employer's prescription drug coverage is at least as good as Medicare Part D.
• HIPAA Special Enrollment Notice: Required at or before the time an employee is first offered enrollment, this notice informs employees of their rights to enroll outside of open enrollment if they experience a qualifying life event.
• HIPAA Notice of Privacy Practices: Required for self-insured health plans at the time of enrollment for new enrollees, and at least once every three years for existing participants.
• Summary Plan Description (SPD) or Summary of Material Modifications (SMM): If your plan design or costs have changed for 2027, communicate those changes through an updated SPD or an SMM before the new plan year begins.

Employers should also maintain records of distribution dates for compliance purposes. "Employers may provide these notices electronically for efficiency at the same time employees are making their benefits elections," says Robb Winger Jr., Senior Benefit Advisor at Paychex. "When doing so, a best practice is to ensure that an electronic employee acknowledgment is always included. This is another reason that active enrollments are encouraged as a best practice." Consult your benefits provider or legal counsel to confirm all notice obligations specific to your plan type and state.

What Is a HIPAA Special Enrollment Period (SEP)?

If individuals miss the annual open enrollment period, they may be allowed to enroll in a health plan during a special enrollment period (SEP). Under HIPAA, SEPs are designated opportunities for individuals to change or update their current insurance plans or enroll in new plans if they experience a change in status or qualifying life event. These events are defined as circumstances that would affect the household's need for medical care, such as the birth of a child or the loss of a job that currently provides health insurance.

SEPs vary by the type of qualifying event. In most cases, employees must notify their employer of a qualifying life event as soon as possible, and no later than 30 days after it occurs (60 days for loss of Medicaid or CHIP coverage), to start the process. The window to provide supporting documentation can extend to 60 days, but the initial notice generally has to happen within 30. Employers should educate their employees about these deadlines so they don't miss out on electing additional coverage.

9 Open Enrollment Strategies To Improve Your Process and Employee Experience

To make the most of open enrollment, implement the following strategies that streamline the process and enhance the overall employee experience.

1. Start Early With an Open Enrollment Communication Strategy

Nearly half of U.S. workers say they don’t understand all of their benefits information. These employees often let their current elections roll over to the next year, even if other options could be more beneficial to them. That’s why it’s never too early to start sharing information, defining key terms like PPO and HMO, and giving employees a chance to ask questions. When developing your open enrollment communication strategy, consider the best ways to deliver information to your team. For example, if you have employees working remotely or in a hybrid work setup, you may need to use non-traditional channels, such as offering virtual benefits sessions. Starting early ensures that every employee has the information they need and allows for unexpected delays.

Before enrollment season, contact vendors to determine when new information will become available and how you can relay it to your employees. You can also conduct company-wide surveys to gauge employee satisfaction with current plan options and get their input on changes they would like to see in the year ahead.

In 2027, it’s even more important that you start your communications early. Begin sharing plan information and cost comparisons as soon as your carrier makes them available, and aim to open your internal enrollment window well before the federal marketplace deadline.

2. Allow As Much Lead Time As Possible

Along with starting communications early, build in as much lead time as possible between sharing the initial information and your enrollment deadline. Employees may need time to coordinate with spouses or partners as they determine which coverage will best protect their families, and new employees or those registering remotely for the first time may need extra support.

Give your employees plenty of time to:

• Review benefits information
• Ask questions
• Coordinate with family members
• Think about their benefit elections
• Evaluate any change in benefits needs

After your initial communication, send regular reminders to keep the upcoming deadline on your team’s radar.

3. Use Multiple Channels to Send Out Information on the Benefits Enrollment Period

One of the most common reasons employees don't participate in benefits programs is a simple lack of information. To empower your employees to make informed decisions, offer information about benefits and plan changes through multiple channels.

You can also use different formats to accommodate a variety of learning styles and serve as reminders for your whole team. For example, some vendors now offer comprehensive plan overview videos or benefits comparison charts that help employees digest large amounts of detailed information.

Consider making benefits information available to employees through:

• Employee benefits websites
• Emails
• Newsletters
• Home mailings
• Webinar presentations
• Text messages

Text messaging is an often overlooked but highly effective channel. Reminders boost response rates and ease the load on your HR team, and even a single text a week before your deadline can help improve participation.

In addition to your internal communication strategy, applicable businesses must adhere to Affordable Care Act regulations. These cover the distribution of electronic summaries of benefits and coverage, their availability, and when materials must be provided. Mark these deadlines and ensure the content meets legal standards to maintain benefits compliance.

4. Offer a Self-Service Option

Self-service options for employee benefits let employees review benefits and make adjustments online, on their own time, without disrupting their workday. A self-service portal can save your employees and your HR team valuable time during busy work periods.

Self-service enrollment may also be the only way to enroll your team if most of your workforce is remote, hybrid, or spread across multiple states. This option gives your employees the freedom to enroll at their earliest convenience without contacting you directly or using mail-in forms.

5. Provide HR Support for All Open Enrollment Options

Employees are more likely to embrace self-service when they know knowledgeable HR support is still available to them.

To achieve this balance:

• Offer virtual drop-in Q&A sessions from insurance carriers or your HR team to address questions and review plan variations from remote or hybrid workers
• If you have employees on-site, invite insurance carriers/agents to make in-person presentations where employees can ask questions directly
• Provide email addresses, phone numbers, and websites employees can use to get more information

6. Hand Out Printed Materials and Other Resources

Many companies distribute open enrollment packets to all in-person employees during the workday. If you have remote or hybrid workers, you can deliver resources via postal mail or email. If you use the postal service, allocate enough time for delivery and create a follow-up process to ensure every team member receives a packet. Email gets information into your employees' hands faster and reduces shipping costs, but not all insurance carriers offer digital formats.

Depending on your situation, you may need to create some benefits documents specific to your company and your benefits offerings. Easy-to-read printed materials like summaries or FAQs are helpful for open enrollment, especially when they include side-by-side comparisons of:

• Premiums, projected employee contributions, and deductibles
• Lists or links to/of in-network medical facilities and consulting physicians
• Changes in plan offerings from the past year to the upcoming year

7. Consider Benefits Enrollment Software

Benefits administration software is built to help you manage your offerings and help employees make benefits choices easily. For example, many platforms offer:

• A centralized administrator dashboard
• An employee benefits portal where team members can access benefits plans, update their information, and enroll
• Reports and compensation statements
• Built-in compliance checks and reporting features

8. Use AI and Decision Support Tools

Even with strong communication and support, many employees struggle to compare plans and choose confidently. Decision-support tools, like AI-powered platforms and benefits navigation apps, help by organizing information, flagging coverage gaps, and answering questions in the moment. Many include side-by-side plan comparisons, cost calculators that estimate out-of-pocket expenses, and step-by-step guidance through the options.

These tools work best alongside human guidance, not in place of it. Pairing them with benefits consultants, live webinars, or short microlearning sessions gives employees a place to ask follow-up questions and feel confident in their choices. Paychex Flex® brings several of these capabilities together, giving employees one portal to compare plans, review costs, and enroll.

9. Track Results and Follow Up After Enrollment Closes

Your open enrollment process does not end when the enrollment window closes. The data you collect is one of your most valuable tools for improving next year's cycle. After enrollment concludes, review:

• Participation Rates: What percentage of eligible employees enrolled? Did participation increase or decrease compared to last year?
• Plan Distribution: How did employees split across your plan options? If one plan is dramatically over- or under-subscribed, that may signal a communication or design issue.
• Benefits Utilization: Which benefits do employees actually use throughout the year? Low utilization of a valuable benefit often points to an awareness problem, not a lack of interest.
• Employee Feedback: What do employees like and not like about the process? Send a brief post-enrollment survey asking how easy the process was, whether they felt they had enough information, and what could be improved.

Use this data to refine your communication strategy, simplify your materials, or adjust your plan offerings before the next open enrollment cycle.

Tips To Improve Your Company's Current Benefit Open Enrollment Process

As the federal open enrollment period approaches, prioritize reviewing your process to ensure you adequately support your employees. Take time to connect with employees and ask for their input on how you can improve. For example:

• Do they understand what benefits are available?
• Are there areas where they need clarification or more information?
• What benefits should you add to meet their needs or wants?
• Do they know how to get support if they have questions?

More options aren't always better. Offering every plan your carrier makes available can overwhelm employees and lead them to choose benefits that don't fit their needs. Instead, focus on two or three plans that cover most situations, such as one co-pay plan and one qualified high-deductible health plan (HDHP) paired with an HSA.

This approach can:

• Highlight the value of your benefits
• Simplify decision-making for employees
• Reduce stress for your HR team
• Ensure you meet vendor deadlines
• Boost employee satisfaction