Background and Objective: Doctors should have full loyalty to their patients, while patients should be able to trust that physicians will act only in their best interests. However, doctors may be faced with situations where they must choose between the patient’s interests and those of a third party. This article presents the results of a study that aimed to identify situations of duality in the decision-making process of medical workers, which can compromise their ethical behavior. Materials and Methods: A cross-sectional study was carried out on a sample of 1070 participants, employed in 120 healthcare facilities in the Republic of Moldova. An online questionnaire was completed anonymously. Descriptive statistics for discrete data were performed by estimating absolute and relative frequencies. To perform the multivariate analysis, the logistic regression was applied. Results: A large number (74.4%) of respondents admitted that they had faced situations of conflicts of interest. Every third respondent (35.3%) had experienced ethical dilemmas when access to expensive treatments should be ensured. Every fourth respondent experienced a conflict between the patient’s interests and those of the institution (26.1%) or the insurance company (23.3%). As age increases, the probability of reporting the dilemma decreases. Physicians reported such dilemmas almost 3 times more often than nurses. A low rate of staff sought support when faced with dilemmas. Half of the respondents (50.6%) preferred to discuss the problem only with a colleague, and 40.1% preferred to find solutions without anyone’s help. There were significant gaps within organizations in terms of the ethical dimension of the decision-making process. Conclusions: Managers should adopt clear institutional policies and tools to identify and prevent situations of dual loyalty. Ethical support should be offered to employees facing such situations. The need to promote an institutional climate based on trust and openness becomes evident.