Objective: Alveolar osteitis is a painful complication that often arises after tooth extraction, presenting a significant clinical challenge. It is imperative to gain a comprehensive understanding of both its occurrence and the contributing factors to enhance the quality of dental care. The aim of this study was to assess the frequency and prevalence of alveolar osteitis among patients and compare these variables based on demographic characteristics (age and sex), the number of teeth extractions, operator experience, health status, and smoking habits in the target population. Methods: This cross-sectional observational study was conducted from May 2019 to April 2020. It included all patients above 16 years of age, of both genders, who underwent permanent tooth extraction for various reasons. Patient demographics, smoking habits, health status, operating dental surgeon’s clinical experience, extraction technique, and the number of teeth extracted were recorded. Statistical analysis was performed using SPSS version 25. Chi-square test and regression analysis were used to assess differences between age, sex, smoking habit, dentist category, and the number of teeth extractions in relation to alveolar osteitis. Results: A total of 679 permanent tooth extractions were performed in 438 patients. Alveolar osteitis was observed in 107 cases (15.7%) following tooth extractions. Among these, 36 cases (33.6%) occurred in single tooth extraction cases, while 71 cases (66.4%) were present in patients with multiple extractions. Moreover, 67 cases (62.6%) of alveolar osteitis were found in cigarette smokers. In addition, 61 cases (57%) of dry sockets were reported after tooth extractions performed by dental interns, while 46 cases (43.0%) were noted in extractions performed by experienced dental surgeons and specialists. Conclusion: The study found a 15.7% incidence of alveolar osteitis in tooth extraction patients in the Al-Jouf region. Alveolar osteitis was more prevalent in males and the age group of 56–77 years. Multiple tooth extractions were associated with higher alveolar osteitis incidence, while operator inexperience increased post-extraction complication risks. In addition, a promising novel protocol and risk assessment scoring system have been devised which require further validation and future research.