Most HR teams still think of open enrollment as an October event. The window opens, communications go out, elections come in, and by mid-November/December, the process is largely complete.

But the employers that run the smoothest open enrollments are rarely the ones moving fastest once October arrives. They are the ones that started making important decisions weeks, and even months, earlier.

By the time the enrollment window opens, many of the decisions that will determine whether the experience is successful have already been made. 

Why September Matters More Than It Used To

Starting early is no longer simply an operational best practice. Open enrollment has become more complex, the stakes are higher, and both HR teams and employees are navigating more pressure than ever.

HR teams are generally advised to begin preparing for open enrollment roughly 90 days before the enrollment window begins, with key checkpoints at the 60- and 30-day marks, according to a Rippling guide for employers. For a typical October or November enrollment period, that 90-day milestone falls squarely in the second half of summer, making September one of the last opportunities to make thoughtful decisions before the pace accelerates.

At the same time, the financial stakes continue to rise. Mercer projects healthcare costs to increase 6.7% in 2026, the steepest increase in fifteen years, making cost management an even greater priority for employers.

Employees are facing challenges of their own. According to data cited by BambooHR, only 27% of employees say they fully understand their coverage, while 39% report delaying or skipping care because they were confused about what their plan covered. A separate Equitable study found that 53% of eligible workers regret the benefits choices they made, and nearly one in five said they did not fully understand their options when making those decisions.

Rising costs and increasing employee confusion are putting pressure on HR teams from both sides. Trying to address those challenges during a short fall enrollment window can make even a strong benefits program feel difficult to navigate.

What Should Already Be Moving

That does not mean every detail needs to be finalized by September 1. It does mean several foundational decisions should already be underway, when there is still enough time to evaluate options thoughtfully and make adjustments.

• Plan and carrier confirmations. Renewal terms, rate changes, and new offerings should be confirmed before employee communications are developed. Cost estimates or plan details that change after they have been shared can quickly create confusion and erode trust in the process.
• A clear understanding of last year. Utilization data, common employee questions, enrollment trends, and friction points from the previous cycle can provide some of the most valuable inputs for this year’s strategy. Reviewing that information early gives HR teams time to address recurring challenges rather than rediscovering them once enrollment is underway.
• Defined goals for this cycle. Whether the objective is encouraging participation in particular plans, increasing voluntary benefit enrollment, improving employee understanding, or reducing the volume of HR support requests, clearly defining success early helps shape every communication, technology, and support decision that follows.
• A communication strategy, not just a communication date. Effective open enrollment communication requires more than deciding when the first email will be sent. SHRM guidance emphasizes starting early, reinforcing key messages across multiple channels, and providing employees with resources such as FAQs, calculators, and concise educational content tailored to different audiences.

Give Your Team a Head Start

September may not feel urgent, and that is precisely what makes it valuable.

The organizations that treat this period as the true beginning of open enrollment have more time to make deliberate decisions, identify potential challenges, and build an employee experience that feels clear and intentional rather than rushed.

By the time the calendar turns to Q4, the goal should not be to start building your open enrollment strategy. It should be to put a well-planned strategy into motion.

Download our latest guide, 10 Tips for a Successful Open Enrollment, for practical strategies to help your team plan ahead, reduce administrative pressure, and create a clearer, more connected enrollment experience for employees.

Get your free copy today and start building a more successful open enrollment strategy.