The Ultra-Orthodox Jewish community embraces a system of values and a rigorous behavioral code that are deeply rooted in religious tradition and history. Here we describe some of the unique challenges that stem from the encounter between modern medical practice and the Ultra-Orthodox world. Through examples of clinical and ethical scenarios ranging from prenatal care to end-of-life decisions, we illustrate problems related to observance of age-old practices in a modern hospital setting, balancing acceptance of Divine will with standard risk assessment, reconciliation of patient autonomy with deference to rabbinic authority and fear of stigma associated with mental illness in a traditional society. We also offer a generalizable model where inquiry precedes pre-formulated judgment to help clinicians provide enhanced care for this population.