At which career milestone should a sailor be approaching retirement to request a twilight tour?

Requesting a twilight tour is typically associated with the period just before a sailor's retirement, allowing for a transition into civilian life while still benefiting from military service. The most appropriate time for this request aligns with broader military policies geared towards easing the transition for sailors nearing the end of their careers.

As sailors approach 30 years of service, they are generally in a position to retire and may start considering options that facilitate a smoother exit from active duty. The twilight tour is designed to provide members an opportunity to serve in a less demanding role while preparing for retirement. This aligns with the standard practices within the military for those approaching that pivotal point of career completion.

While transitions may occur at various points in a sailor's career, the 30-year mark specifically supports the concept of ensuring personnel have adequate time to secure benefits and prepare for their next steps, making it the ideal milestone for requesting a twilight tour.