I used to run benefits enrollment for a small (<500 FTE) company. It was always a cluster fuck. Online enrollment (rather than paper) helped improve things a little. I would sit with employees (& spouses!) & help with filling out forms. I would hand & email confirmations to everyone. I would “extend” open enrollment by two weeks (really just starting two weeks early so that we could catch errors). If somehow an error occurred or a change needed to be made, I lied my ass off/argued until I got the insurance companies to make sure employees got the coverage they needed. A good HR person should do that - unfortunately, the field is filled with craven bureaucrats who like punishing people for checking the wrong box. As bad as payroll clerks. Glad I’m out of that game. 
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