Objective: This study aimed to assess the compliance and satisfaction of third-year undergraduate dental students and patients using the Dental Information Archiving System (DIAS) in a private dental college in Chennai, focusing on ease of use, time efficiency, and overall experience. Methods: A prospective trial was conducted at Saveetha Dental College, involving 100 dental students and 100 patients. Compliance and user satisfaction were measured using a questionnaire administered at two-time points: at the initial clinical appointment and after four weeks of using DIAS. The questionnaire included multiple-choice and Likert-scale questions addressing key aspects such as ease of use, perceived value, and efficiency of the system. Results: Patients: Awareness of DIAS increased significantly from 78% to 96% between the first and second visits. Patient satisfaction with the software’s time efficiency and perceived security improved drastically, with 93% finding the time spent reasonable by the second visit (p = 0.000). Confidence in data security rose from 4% to 85% (p = 0.000). Students: Familiarity with DIAS improved from 7% to 61% (p = 0.000), and preference for DIAS over traditional methods increased from 28% to 67% (p = 0.000). The time required for DIAS usage decreased, while the application of clinical knowledge increased from 67% to 74% (p = 0.008). Conclusion: The study demonstrated that both students and patients showed significant improvements in compliance and satisfaction with the dental software over time. Increased exposure led to better understanding and trust in the system, highlighting the potential of DIAS to enhance clinical education and patient care. However, challenges related to data security, interoperability, and the need for ongoing training remain critical for wider implementation.