Aim and objective: The aim and objective of this study was to investigate the factors that influence the choice of specialty and career preferences in dental students and interns in their clinical years. Materials and methods: This cross-sectional study was performed in the 5th-year and 6th-year dental students and interns at Taif University in Saudi Arabia. A self-administered questionnaire was formulated and sent electronically to the students via faculty e-mail. The responses were recorded on a Google spreadsheet, and the data were analyzed using SPSS for Windows. Results: The majority of dental students expressed a preference for pediatric dentistry and restorative and esthetic dentistry. The main factor influencing their choice was the local shortage of dentists in these specialties. Negative experiences of students, their peers, or faculty members also affected the students’ career choices. Conclusion: This study provides baseline data for establishing plans to improve graduate programs in Saudi Arabia. Mentoring initiatives are needed to provide guidance and encouragement for undergraduate dental students when selecting the most appropriate future specialty. Clinical significance: The choice of dental specialty is a challenge for dental students and is affected by many factors. The knowledge of the factors that influence their choice of specialty would help when addressing the requirements of job market.