The livelihood of the Maasai pastoral communities in Longido District of Northern Tanzania are impacted by droughts regularly, with expectations of increasing variability in rainfall patterns the coming years due to climate change. The goal of this research is to explore if weather forecast and remote sensing data can be tailored to existing coping strategies and decision-making. Furthermore, it is assessed if this tailored information provides enough skill to effectively complement local knowledge and drought management strategies. The study generated important methodological and theoretical findings, both of which have practical implications for policy and technological development. An ethnographic and participatory approach, including four months of immersion with local families, was used to document local knowledge and strategies, and understand what specific, weather information may benefit pastoralists. The study focused on alamei periods, which refers to times of drought and scarcity in the Maasai language. It revealed that weather information around particular important ‘decision junctures’ is most relevant. On the one hand, decisions to move livestock during vulnerable times are based on current water and grass availability; on the other hand, families also consider expectations of rainfall in their decisions. The research determined that at very specific junctures throughout respective seasons, key, timely decisions must be made to maintain household resiliency. It is at these junctures that rainfall predictions become crucial. Using NDVI data and the ECMWF weather model, it was assessed if the onset of rains at such junctures can be predicted with enough skill to support livestock movement decisions. It revealed both optimism and scepticism about the role of current remote sensing and weather prediction technologies vis-à-vis variable, dryland ecologies and pastoral livelihoods.