Much of the focus of climate variability in tropical regions is centered on the conditions during the wet season. Monsoonal rainfall, different phases of the Madden-Julian Oscillation and multiple seasonal climate drivers such as the Indian Ocean and El Niño Southern Oscillation interact at different time scales and influence rainfall patterns and extremes across the tropical North. Much less attention has been paid to dry season climate variability, which can be influenced by early storms and occasional rainfall events. Unseasonal rainfall events and anomalous temperatures impact agricultural productivity affecting fruit set opportunities, ripening times and harvest windows. Here we explore dominant modes of climate variability and quantify the impacts on rainfall and temperature and their seasonal variations. We identify gaps in seasonal forecast system and how additional forecast skill can aid the risk reduction of these decisions. We show that a substantial part of rainfall variability during the dry season can be explained by the interactions of the El Niño Southern Oscillation and the Indian Ocean conditioned by different phases of the Madden-Julian Oscillation.