This study examined the effectiveness of online education to providers who serve people experiencing homelessness, comparing online and face-to-face training of Critical Time Intervention (CTI), an evidence-based case management model. The authors recruited 184 staff from 19 homeless service agencies to participate in one of two training conditions: (a) Online Training + Community of Practice or (b) Face-to-Face Training + Telephone Consultation. Each group received 24 hours of instruction and support. Through baseline, follow-up, and nine-month post-training surveys, the authors examined satisfaction, knowledge gains, knowledge retention, and readiness to implement CTI. While satisfaction rates were higher among participants in the face-to-face group, the two training conditions produced comparable pre/post knowledge gains. Furthermore, both groups showed increased knowledge retention scores at nine-month follow up, with the online group scoring higher than the face-to-face group.