Unaffiliated Jews often maintain deep spiritual connections to religious observance while avoiding formal synagogue participation - a paradox that challenges traditional models of Jewish community engagement. Over five years of leading Yom Kippur Yizkor services in Forest Hills, New York, attendance surged from 100-150 to more than 500 participants, revealing significant unmet spiritual needs among disconnected Jewish populations. Through participant observation and reflective analysis, the research identifies economic barriers, unfamiliar worship practices, unwelcoming atmospheres, and congregational politics as key factors driving synagogue avoidance. The methodology centered on creating inclusive worship environments that balanced familiar elements with traditional liturgy while maintaining a nonjudgmental approach. Extended work with Jewish Alcoholics and Chemically Dependent (JACS) communities further illuminated how addiction issues permeate all segments of Jewish life, from unaffiliated to Orthodox populations. These findings demonstrate that Jewish communities must develop more welcoming approaches to serve marginalized populations, with chaplaincy and outreach programming offering effective bridges between affiliated and unaffiliated Jewish populations while addressing broader trends of declining synagogue participation.