Introduction After 54 years of Assad’s family dictatorship, Syria was finally free but, nonetheless, was in ruins. The health profession education training system is no exception, and there have been many indicators of this in the literature, but none of them have provided a systematic evaluation of the clinical learning environment (CLE) using validated approaches. Therefore, this study aimed to evaluate CLE at teaching hospitals in Damascus, Syria. Methods This cross-sectional study was conducted in Damascus, Syria, during mid-2023, before Assad’s regime collapsed. The study population included all resident doctors working and training at any teaching hospital in Damascus. We used the recently validated 36-item PHEEM inventory as a data collection tool and added 10 extra items related to Syria’s specific context. There was also one open-ended question. We recruited participants from 14 different teaching hospitals using nonprobability sampling techniques. Results A total of 1490 residents from 31 medical specialties participated in the study, which was approximately 37% of the total population at that time. The female participants comprised 50.7% (n=754) of the total sample. The Cronbach’s alpha was 0.925. The total PHEEM mean score was 72.4±21.4 (Max. 144). All the PHEEM domains showed significant shortcomings, except for learner engagement and social participation. The worst-scoring domains were external regulation, work culture, and living conditions, with scores of 48.5%, 40.8%, and 31.2%, respectively. The results of the additional 10 war-related items were important. One item showed that only 14% of respondents did not have plans to migrate. The written comments re-echo some of the PHEEM findings in more context. Discussion This study draws a roadmap for clinical educators, lawmakers, and new leaders to make targeted reforms and investments to restore the clinical learning environment. There are major issues that not only render training residents suboptimal but also compromise residents' and patients’ safety.