A patient, nowadays, acquires health information from the Web mainly through a “human-to-machine” communication process with a generic search engine. This, in turn, affects, positively or negatively, his/her empowerment level and the “human-to-human” communication process that occurs between a patient and a healthcare professional such as a doctor. A generic communication process can be modelled by considering its syntactic-technical, semantic-meaning, and pragmatic-effectiveness levels and an efficacious communication occurs when all the communication levels are fully addressed. In the case of retrieval of health information from the Web, although a generic search engine is able to work at the syntactic-technical level, the semantic and pragmatic aspects are left to the user and this can be challenging, especially for elderly people. This work presents a custom search engine, FACILE, that works at the three communication levels and allows to overcome the challenges confronted during the search process. A patient can specify his/her information requirements in a simple way and FACILE will retrieve the “right” amount of Web content in a language that he/she can easily understand. This facilitates the comprehension of the found information and positively affects the empowerment process and communication with healthcare professionals.