WASHINGTON—The Air Force is taking steps to address a chronic shortage of drone pilots, sweetening the allure of flying the unmanned planes as part of a plan to alleviate the strains as it tries to meet demands for drones and the video intelligence they provide.

Secretary of the Air Force Deborah Lee James is expected to announce a plan Wednesday to give Air Force pilots thousands of dollars in bonus pay if they sign up to fly the remotely piloted craft for five years or more. Ms. James also is directing that for the next...