A structural bolt security apparatus includes a security nut forming a threaded central hole for a bolt; the security nut has a groove in an upper surface and/or a side surface. At least one groove is at least partially separated from the threaded central hole by the upper surface. In one embodiment, a security nut has a plurality of electrical contacts, logic electronics configured for monitoring electrical resistance across the electrical contacts, and a transmitter for broadcasting security data generated by the logic electronics. In one embodiment, a structural bolt security apparatus includes a security nut and an outer sleeve. Structural bolt security systems described herein include a security nut, a security socket, and a security wrench. The systems may be equipped with RFID chips for recognition of matched security nuts and security sockets, and/or with GPS transceivers for broadcasting security wrench position information.