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Most states exempt public charter schools from state policy that regulates the mentorship of new teachers. Regardless, there are charter systems that develop teacher mentor programs on their own. These system-created programs can create a dichotomy between charter expectation and mentor/mentee experience. Utilizing a case study approach, this paper offers a unique view into this phenomenon, by examining the inaugural year of a mid-sized urban charter system’s effort to design and implement a teacher mentoring support program. Data include interviews with 15 teachers (paired and unmatched mentors and mentees) and administrators, meeting observations, and reviews of program documents and artifacts. Findings note challenges related to support, guidance, and expectations, in addition to a cautious optimism about future charter mentor endeavors.