Digital technologies are now central to how learning facilitators coordinate work, sustain participation, and demonstrate reliability in technology-integrated environments. For those with multigenerational caregiving responsibilities, technology simultaneously enables continuity and intensifies coordination demands. Guided by the HRD-CARE model—which conceptualizes caregiving through care-role complexity, temporal–emotional load, and the employment interface—this qualitative study examines how learning facilitators use digital tools to sustain full-time employment while navigating competing caregiving obligations. Findings show that technology functions as continuity infrastructure, supports boundary work through digital coordination, and contributes to developmental trade-offs when time and energy are constrained. Although technology expands feasible participation, it does not eliminate role collision and may increase the visibility of caregiving-driven variability at key developmental gateways. The study advances HRD scholarship by demonstrating how caregiving conditions shape participation, development, and access to opportunities in technology-integrated work