After the divorce, Sybil worked during World War II as a teacher for the Ellis Mining Company in Bourne, Oregon, and buying a $150 house in nearby Sumpter for herself and her son.
Plumlee also occasionally worked as a soda fountain clerk at a drugstore in northeast Portland, and as a cab driver.
[3] While Plumlee was working as a caseworker for the welfare department of Clackamas County, a female police officer encouraged her to take a civil service test.
She passed the test, and was selected from a pool of 300 applicants to fill the Portland Police Bureau's only open position.
The family needed her income: Paul, a World War II veteran, suffered from posttraumatic stress disorder and had difficulty holding steady jobs, and Plumlee was also contributing to the support of her aging mother.
[6][7][8] Records show that she also participated in undercover investigations, including an anti-homosexual campaign organized by Mayor of Portland Dorothy McCullough Lee.
[11] In 1959, two brothers were charged with disorderly conduct and destroying city property after tearing the speaker system from a police car occupied by Plumlee and another female officer.
At a 1964 Portland Yacht Club luncheon called "Women with the Badge", she told female attendees how they should protect themselves and their children.
Guests included Multnomah County Sheriff Daniel Staton, her great-niece Lieutenant Mary Lindstrand, also from the Multnomah County Sheriff's Office, and Frank Springer, then age 99 and the oldest living male retiree of the Portland Police Bureau.
Birthday wishes and certificates of appreciation were also presented to her from President Barack Obama and Mayor of Portland Sam Adams.