Maintainers of most open source projects long for everlasting engagement from their contributors. Community-driven projects stand a better chance at this, provided the community itself is well-fed with new contributors and fresh ideas. Contributors may begin their journey with many motivations, however staying and taking on maintenance responsibilities is aided by the community's culture and willingness to mentor. We began building engagement for the OpenStack Manila community years ago with one-on-one mentoring of new contributors. We scouted for interested folk at events, conducted hands-on workshops and continuously improved our on-boarding documentation. Our methods constantly changed with feedback from mentees. After mentoring nearly two dozen Outreachy, GSOC and college interns from across the world, we want to share our process and learnings through this presentation.