Background/Objectives: Digital triage systems are increasingly used in dentistry to support patient access and improve service efficiency, particularly in academic and public healthcare settings. However, limited evidence exists on how these systems function in practice from the perspectives of both patients and providers. This study aimed to explore patients’ and staff members’ experiences, perceptions, and expectations of a digital dental triage system at a teaching dental hospital. Methods: A qualitative descriptive study was conducted at the Dental Teaching Hospital of Umm Al-Qura University (DTH-UQU), Saudi Arabia. Semi-structured interviews were carried out with 25 participants, including dental professionals, administrative staff, and patients who had recently used the digital triage system. Interviews were audio-recorded, transcribed verbatim, and analyzed using Braun and Clarke’s thematic analysis approach. Results: Analysis identified six interconnected themes. Patients generally found the system easy to use and consistent with their digital habits, yet this usability did not translate into satisfaction due to limited communication, post-registration silence, and unclear care pathways. Staff emphasized clinical accuracy, educational requirements, and capacity constraints as key drivers of triage decisions that were often invisible to patients. Communication breakdowns, misclassification, duplicate registrations, and unmet expectations emerged as central challenges, contributing to workflow inefficiencies. Participants suggested that improvements focused on enhanced communication, guided data entry, system integration, and expanded teledentistry functionality. Conclusions: The effectiveness of digital dental triage systems depends not only on usability but also on transparent communication, alignment with institutional capacity, and integration within broader care pathways.