ONE's journey deploying chatbots for advocacy work from 2018-2024 provides valuable insights into operating messaging systems at scale for social impact. Starting with a shift from SMS to Facebook Messenger, and later expanding to WhatsApp, ONE developed two chatbots reaching over 38,000 users across six African countries. The project demonstrated both the potential and limitations of non-AI chatbots, achieving 17,000+ user actions while identifying key challenges in user acquisition costs ($0.17-$1.77 per user), retention, and re-engagement restrictions. Their experience highlights the importance of starting small, continuous user testing, marketing investment planning, systematic re-engagement strategies, and organization-wide integration of chatbot initiatives.