The results of an investigation of thermomechanical fatigue (TMF) on a superalloy specimen, with an applied thermal barrier coating (TBC) and a circular through hole, are presented. Tensile loads were applied in phase with increasing temperature. Damage evolution in the form of cracks develops in the TBC adjacent to the hole. These cracks run perpendicular to the loading axis. Stress mapping of the thermally grown oxide (TGO) using luminescence spectroscopy determined an increase in compressive residual stress with increasing TMF cycling. Scanning electron microscopy examination, following cross sectioning, determined the TBC cracks to be vertical separations of the columnar yttria-stabilized zirconia (YSZ) top coat. Microscopic damage mechanisms in the form of plasticity (bending of YSZ columns) and TGO cracking were observed. Imperfections in the bond coat are associated with these vertical separations. Energy-dispersive element mapping of these imperfections indicated a composition of alumina and mixed Cr, Co, and Ni oxides.