This paper looks at challenges faced during the ongoing deployment of HEALER, a POMDP based software agent that recommends sequential intervention plans for use by homeless shelters, who organize these interventions to raise awareness about HIV among homeless youth. HEALER’s sequential plans (built using knowledge of social networks of homeless youth) choose intervention participants strategically to maximize influence spread, while reasoning about uncertainties in the network. In order to compute its plans, HEALER (i) casts this influence maximization problem as a POMDP and solves it using a novel planner which scales up to previously unsolvable real-world sizes; (ii) and constructs social networks of homeless youth at low cost, using a Facebook application. HEALER is currently being deployed in the real world in collaboration with a homeless shelter. Initial feedback from the shelter officials has been positive but they were surprised by the solutions generated by HEALER as these solutions are very counter-intuitive. Therefore, there is a need to justify HEALER’s solutions in a way that mirrors the officials’ intuition. In this paper, we report on progress made towards HEALER’s deployment and detail first steps taken to tackle the issue of explaining HEALER’s solutions.