Nowadays, people’s lives are based on national collaboration, regional connections, and global communication. It has become a must to follow the new technological development and digitalization, and to cope with or tackle the needs of the new era. Hence, these new requirements have transformed the role of the teacher to be only a guide who can direct students to the right track, and the role of the students to be the inquirers who are deeply engaged in the teaching-learning process. Consequently, developing critical thinking among learners through digital means and tools became a must to develop language proficiency and facilitate communication. This paper is going to shed light on the impact of implementing critical thinking techniques through the use of technology, Flipped Learning FL, on improving oral proficiency and overcoming speaking challenges in this digital period. The research followed the quantitative method in which a questionnaire was answered by participants of language teachers in private schools that are using Flipped Learning in Mount Lebanon.