Supporting effective and enjoyable Web usage by people with sensory, motor and cognitive impairments requires more than just accessible Web content. There is an additional task of matching people with an accessibility solution that best accommodates their particular needs -which, especially for older Web users, may fluctuate in severity, number and combination. Lack of awareness of one's own accessibility needs and the solutions that may exist to accommodate them may lead to a reduced quality Web browsing experience or even abandonment.This paper discusses the difficulties in matching people with less severe, but multiple, impairments with the most appropriate accessibility features at a given time, and explores the role of automated or semi-automated adaptations as a solution for this problem. We review related work, and report on the early stages of our own work conducted to prove the concept of adaptations for accessibility in the specific context of supporting Web users with age-related capability decline. We also consider the potential ethical issues of automated and semi-automated accessibility adaptations on the wellbeing of older Web users, and how these might best be managed in a suitably sensitive way.