Background. Endometriosis is a chronic gynecological disorder affecting a substantial proportion of women of reproductive age and is associated with impaired quality of life, absenteeism, presenteeism, and reduced work participation. Despite its potential occupational implications, evidence on how occupational physicians (OPs) manage workers affected by endometriosis remains scarce. This study aimed to assess knowledge, attitudes, and practices (KAP) regarding endometriosis among Italian OPs. Methods: A cross-sectional web-based survey was conducted between 1 and 18 April 2026 among members of an Italian discussion group restricted to occupational physicians. The questionnaire investigated demographic characteristics, knowledge of endometriosis, risk perception, perceived barriers to workplace management, and previous experience in issuing conditioned fitness-for-work appraisals. Multivariable logistic regression was performed to identify factors independently associated with having previously issued work restrictions because of endometriosis. Results: A total of 155 occupational physicians participated in the survey. Most respondents considered themselves adequately informed about endometriosis (78.1%) and reported previous professional experience with affected workers (81.3%). However, objective knowledge revealed important gaps, particularly regarding disease prevalence (26.5% correct responses), familial predisposition (34.8%), and diagnostic pathways (31.6%). The mean General Knowledge Score was 64.1% (95%CI 62.2–66.1), while only 11.0% of respondents reported awareness of occupational recommendations specifically addressing endometriosis. Overall, 65.8% of participants reported having previously issued conditioned fitness-for-work appraisals, most frequently recommending increased work breaks, avoidance of night shifts, or limitation of shift work. In multivariable analysis, male gender (aOR 5.69, 95%CI 1.84–17.58), participation in continuing medical education activities (aOR 85.72, 95%CI 6.60–1114.21), information obtained from colleagues (aOR 4.67, 95%CI 1.23–17.77), and employment in healthcare settings (aOR 5.91, 95%CI 1.92–18.16) were independently associated with previous issuance of restricted fitness-for-work judgments, whereas relying exclusively on undergraduate medical education was negatively associated with this outcome (aOR 0.07, 95%CI 0.01–0.39). Conclusions: Italian occupational physicians generally recognized endometriosis as a clinically relevant condition and frequently encountered affected workers in daily practice. Nevertheless, important deficiencies persist regarding epidemiological knowledge, diagnostic issues, and awareness of occupational management strategies. Continuous professional education, interdisciplinary exchange, and practical experience appear to contribute more substantially to occupational decision-making than undergraduate training alone. These findings support the development of targeted educational interventions and shared occupational recommendations aimed at improving workplace management and promoting the inclusion and retention of women affected by endometriosis in the workforce.