As a result of the rapid development of Information and Communication Technology (ICT) and the growing interest in Internet-based tools for language classroom, it has become a pressing need for educators to locate, evaluate and select the most appropriate language-learning digital resources that foster more communicative and meaningful learning processes. Hence, this paper describes a mixed research project that, on the first hand, aimed at proposing a Checklist for evaluating language websites built on the principles of the Communicative Approach, and on the second hand, sought to strengthen the teachers’ Knowing-how-to-do skill as part of their digital competence. To achieve these goals, a four-phase research procedure was followed that included reviewing relevant literature and administering qualitative and quantitative research methods to participants (i.e., language teachers, an expert in the Computer-Assisted Language Learning (CALL) field and a college professor) in order to gain insights into problematic issues and, thereafter, to contribute to the creation and validation of the Checklist model and the Study Guide. The findings revealed that: (a) evaluating language websites leads to the enhancement of the teachers’ practical skills and their knowledge of the technological language; and (b) having an assessment instrument allows educators to choose the materials that best meet their communicative teaching purposes.