Substantial research illuminates many factors effecting the implementation of evidence-based mental health promotion programs in schools; however, research on how schools plan for sustaining their investments in these programs is limited. In this qualitative study, we elicited descriptions of opportunities and challenges for sustainability. We interviewed 24 individuals from schools involved in a longitudinal, qualitative research project that followed uptake and implementation of the evidence-based WITS Programs across 2 years (Leadbeater et al. 2012). WITS stands for Walk away, Ignore, Talk it out and Seek help and the online WITS Programs focus on preventing peer victimization ( www.witsprograms.ca ). Our findings suggest that sustainability planning in schools is not merely a next step following high quality implementation, but rather involves multiple ongoing processes that need to be anticipated and supported by school leadership and program champions and developers in order to realize investments in evidence-based programs.