You back out of a parking spot and clip a concrete pillar. The bumper’s cracked, the sensor’s dangling, and now comes the dreaded part: filing a car insurance claim. You open your insurer’s app, but it asks for a login you don’t remember. You try the website, but it keeps timing out. You call the 800 number, only to hit a maze of automated prompts that never get you to a real person.

After twenty minutes of frustration, you close your laptop and tell yourself it’s not worth the hassle.

This kind of scenario is becoming increasingly common among Baby Boomers

A new analysis from Insurity found that 28% of Boomers have avoided filing a claim altogether due to digital roadblocks. Whether it’s complicated websites, glitchy apps, or impersonal systems, many older policyholders are losing patience with an industry that keeps pushing self-service over human connection.

The survey also found that 59% of Boomers prefer to speak with a live representative instead of using a fully digital system. Only 7% described their ideal claims experience as entirely online. Even among Gen X drivers, 39% still want human interaction.

Insurance companies might shrug at the numbers

After all, fewer claims often mean higher profits. If frustrated customers skip the process, the company keeps more money. But that short-term gain can come at a long-term cost.

Baby Boomers remain a major slice of the insurance market. Many have been loyal customers for decades. Ignoring their needs not only hurts brand reputation but also risks driving them to competitors with better support.

Insurity’s data sends a clear message: digital convenience should not replace accessibility. Hybrid models, where technology works alongside responsive human service, can give drivers the tools they need without leaving them stranded in a sea of forms and login screens.

Modernizing insurance is smart business. But leaving people behind isn’t.