Digital technologies in present day interconnect globally, providing a dynamic environment to support the educational needs of any learner within a novel technological ecosystem. The paper discusses the identified aspects of providing relevant digital accessibility to learners with various needs by this ecosystem, such as sensor support, knowledge provision from a variety of digital and non-digital repositories, and support to the motivation of the learner to acquire better knowledge in the classroom, museum, or in rehabilitation. A novel tool for assessment of such technological ecosystems, called Accessibility Barometer, is described.