While most technologies remain at best primarily reactive, adapting only to current contexts or explicitly configured parameters, pro-adaptive technology represents an emerging research direction that extends this paradigm. Developoed in the context of assistive technology (AT), it considers longitudinal trends, anticipating future changes in user abilities to maintain system effectiveness, usability, and user acceptance over time. We therefore propose different levels of adaptability, ranging from static AT (L1), adaptive AT (L2), personalisable AT (L3) and auto-individualizing AT (L4) to pro-adaptive AT (L5). Pro-adaptive AT adapts to meet the user's (future) needs based on anticipated conditions that are derived from past and current sensor data (e.g., ageing or changes in disease course). In this workshop, we invite demonstrations, talks, and work-in-progress contributions to discuss the future of (pro-)adaptive technology and potential approaches to its implementation, both in AT and beyond. To this end, the workshop unites interdisciplinary researchers and practitioners to advance user-centered, adaptive technology.