Abstract: One embodiment of a fatigue resistant structural connection that has a primary member 19 coupled to a baseplate 17 with a circumferential weld 18. The connection employs the use of a plurality of stiffeners with elongated, contoured tails 30 coupled to the primary member with a longitudinal weld 27 and coupled to the baseplate with a weld 26. These stiffeners are oriented along the longitudinal axis of the primary member and are laid out radially from this longitudinal axis. The present embodiment: mitigates stress concentrations due to discontinuous connection geometry and therefore improves fatigue resistance, adds a degree of structural redundancy to otherwise non-redundant structures, and provides a means of retrofitting existing tall cantilevered structures. Other embodiments are described and shown.