Through intimate letters penned to their mentors at the Jewish Theological Seminary between 1910-1919, pioneering Conservative rabbis revealed the profound struggles of building a new American Jewish movement. These Seminary graduates, trained under Solomon Schechter's vision, found themselves caught between tradition and change as they established congregations across the country. Their archived correspondence illuminates sharp tensions with congregants over liturgical innovations, educational reforms, and the introduction of English into services - conflicts that would shape Conservative Judaism's distinctive identity. Documentary analysis of JTS records shows these early leaders grappling with role ambiguity, positioning themselves between Orthodox and Reform while facing resistance from both traditionalist laity and competing rabbinic authorities. The letters expose a stark gap between Seminary education and congregational realities, as rabbis navigated complex issues of ritual observance, synagogue decorum, and community leadership in diverse settings. Without developed institutional support systems, graduates relied heavily on personal networks and faculty connections for placement and guidance. By decade's end, these rabbis had begun articulating a distinctive "Conservative principle" and establishing organizational frameworks like the United Synagogue that would define the movement. Their experiences reveal how Conservative Judaism evolved from an educational institution's theoretical vision into a coherent denominational movement through practical, often challenging, implementation by its first rabbinic leaders.