Millions work in deskilled jobs, and prior research suggests that advancing out of these jobs within an organization is uniquely difficult:in order to advance, workers must demonstrate skills other than those that their current position gives them the opportunity to develop. Through ourtwo year, nationwide, multi-sited ethnographic study of AI-enabled robotics in e-commerce and parcel warehousing, we both reveal the profoundchallenges to internal advancement out of actively deskilled jobs and the systematic ways in which a small minority of workers managed to do so, inspite of these challenges.