For the second year running, Cascade AI analyzed real, anonymized employee conversations during Open Enrollment, and the shift from 2024 to 2025 is the clearest evidence yet that years of benefits communications, employee education, and open enrollment outreach are paying off. Health plan comparison and evaluation questions grew from 38% of all Open Enrollment activity to 55% in a single year, with employees past basic education questions and into the real work of decision-making, stress-testing costs, running coverage scenarios, and working through the financial implications of the choices in front of them. The organizations that can meet employees at that moment are the ones that will see the outcomes their benefits programs were always designed to produce.
Questions about what an FSA is, when enrollment deadlines fall, and how dental coverage works all fell significantly compared to 2024. Employees were stress-testing costs, running coverage scenarios against specific medical situations, and working through the real financial implications of the choices in front of them. That shift changes what good benefits support looks like.
Employees Who Arrive Ready to Decide Need a Different Kind of Support
Employees who arrive ready to decide need a different kind of support. They need support sophisticated enough to reason through a specific person’s situation, with their plan options, their medical history, and their financial picture, without creating fiduciary risk for the employer. In 2025, that support existed at scale for the first time.
What made the difference was availability, privacy, and the capacity to go deep. Employees do not make benefits decisions at 2 pm on a Tuesday. They make them at night, on weekends, and in the margins of their day, doing the math with a spouse after the kids go to bed, comparing plans on a Sunday morning before the deadline hits. More than 20% of Open Enrollment questions in 2025 arrived outside standard business hours, and the support was there when the benefits team could not be.
When employees knew the conversation was fully anonymous, they stopped asking safe questions and started asking real ones, including questions about cancer diagnoses, fertility costs, depression medications, and financial hardships that would never surface on a call center line. Anonymity did not create those questions. It gave them somewhere to go. And when employees needed to go deep, the support kept up. Nearly 59% of sessions had four or more exchanges, and one employee asked 59 questions in a single sitting, working through health plan cost scenarios, HSA mechanics, and critical illness coverage in sequence, building on each answer before moving to the next. Decision-making, when support can keep up with it, looks exactly like that.
Employees brought their full financial picture
Most Open Enrollment programs assume employees arrive with health plan questions. In 2025, they arrived with their full financial picture. Questions spanned nine benefit categories, including 401(k) planning alongside medical plan decisions, life insurance, and critical illness in the same session, and retirement savings and prescription coverage in sequence. They do not organize their financial lives by department, and they do not organize their benefits questions that way either.
What this means going forward
The 2024 report documented what employees were asking. The 2025 report documents what happens when they have somewhere to take those questions. Employees stop defaulting to last year’s plan and start making active, informed choices about coverage, costs, and financial protection. For HR leaders, that is the difference between a benefits program that exists and one that performs.
That is worth building on.
Read the 2025 Annual Open Enrollment Report to see the full picture of what employees asked, when they asked it, what privacy made possible, and what it means for how you structure Open Enrollment support in 2026.
