A self-sealing roofing nail for reducing or preventing roof leaks. The self-sealing roofing fastener includes a pointed fastener shaft and a fastener head. A small sleeve having a rupturing shell containing a volume of sealant is disposed over the fastener shaft and adjacent the fastener head. When the self-sealing roofing fastener is driven into a structure using a hammer or a nail gun, the shell ruptures and releases the sealant between the fastener head and a structure. The released sealant seals the puncture caused by driving the roofing fastener into the structure.