Objectives: The sudden advent of the COVID pandemic resulted in limited face to face interactions and the dental school in the University of the West Indies was challenged to complete the final year with a rapid transition to online teaching. This study examined students’ and teachers’ perceptions of the effectiveness of emergency remote online teaching and challenges experienced. Materials and Methods: Two independent online cross-sectional surveys were administered on the perception of the online learning environment and challenges experienced and effectiveness of strategies used. Overall thirty three dental students and eleven clinical academic teachers participated. Statistical analysis: Reliability of the questionnaire was determined. Chi-squared (χ²) tests were applied for determining the perceptions of students and teachers towards online teaching. Frequencies and percentages were also computed. Results: The majority of students (60.6% - 69.7%) perceived that online teaching strategies enhanced their clinical reasoning and critical thinking skills in clinical practice and found it easy to adapt. However, the majority (87.9%) perceived it to be somewhat or not effective at all in acquiring clinical skills. The main challenge experienced was connectivity to the internet (87.9%). The majority of teachers (72.7% - 92.9%) perceived that they effectively communicated with the students and engaged students in clinical reasoning and critical thinking, but 50% did not think they prepared students to practice clinical skill. Conclusions: Students’ perceptions are similar to teachers’ perceptions in that both are positive to the online teaching strategies but both groups reflected concerns over the acquisition of clinical skills.