The Boston Public Schools Online Mentoring (BPSOM) program aims to support 2nd and 3rd year teachers through online learning facilitated by veteran educators. Utilizing a wiki platform, BPSOM includes biweekly learning forums, community discussions, and a final portfolio to document progress and reflections. Challenges include high dropout rates in live discussions, insufficient mentor support, and the need for feedback mechanisms, leading to proposed future improvements such as migrating to a Moodle environment and enhancing mentor training.