Assistive Technology (AT) is becoming an integral part of our daily live, supporting people in different areas, for example while driving a car or cognitive demanding tasks at work or home. To date, existing AT is often static or only considers the current situational context and capabilities of a user. Here, the concept of Pro-adaptive Assistive Technology (Pro-CAT) is introduced. Pro-CAT adapts to predictable, temporal changes in the user’s capabilities and contextual situation (e.g., general ageing processes, an expected course of a disease, learning progress during skill acquisition or environmental changes). Pro-CAT can have several advantages: Better adaptation of the users to the system in case of prospectively declining cognitive abilities; Avoidance of “over-assistance” which could lead to unlearning of skills and incapacitation; Predictive assistance that might delay the onset of disability and increase acceptance rates. Among other components, Pro-CAT requires a prognostics module that includes individual competence- and progression models to prospectively predict typical learning, ageing and disease processes and a planning module including prospective memory to provide support at an appropriate (future) time-point. Pro-CAT may use the “Human Digital Twin” framework that strives to model all relevant aspects of a human user and continuously updates its parameters according to observed changes over time. For individuals with Attention Deficit Hyperactivity Disorder (ADHD), reading can be cognitively demanding. This paper presents a Pro-CAT scenario that provides real-time reading support. The planned reading support system will use electroencephalography, electrocardiography and eye tracking to estimate the attentional state in combination with augmented reality technology to assist the reading process. Pro-adaptivity dynamically adjusts assistance based on medication effects, the user’s current state, and long-term ADHD progression.