Professional communication skills have a substantial effect on dental patient satisfaction and health outcomes and are one of the core competencies expected of newly graduated dentists in Australia. Acquisition of effective, goal-oriented communication skills has been shown to improve the dentist-patient relationship and requires both practicing skills and reflective thinking. The use of technologies such as video-recording to communicate directly and individually with students can be used to enhance students’ engagement and communication skills. This paper aims to present the results of the implementation of the video recording of role-plays and self-reflection in the training of communication skills of first-year dental students at Griffith University, Australia. The year 2015 was used as a control, and in 2016 we introduced video recording, and in 2017 self-reflection. The tools used to measure the impact of these teaching instruments were: (1) student evaluation of courses (SEC) data, and (2) results of the final practical exam grades in the Communication Skills for Oral Health Course. The skills assessed and reflected on include: verbal and non-verbal communication, metacommunication, self-confidence, rapport, active listening, and mindfulness. Recordings and facilitator’s feedback can be accessed by each student for their self-reflection on their overall performance, communication skills, patient-centered approach and strategies on how to improve their skills. Results of the SEC data show enhancements in engagement (68–83% +ve answers), assessment (66–78% +ve answers) and feedback (81–89% +ve answers). Results of their average final practical marks increased from 57.82% (control) to 63.34% (with video), and finally 79.64% (with video and self-reflection). These results strongly suggest that the inclusion of the digital recording of role play interactions and self-reflection increases the quality of communication skills training for dental students by enhancing their dentist-patient relationship skills, engagement, confidence, satisfaction with assessment and the quality of the feedback that can be provided.