The delamination resistance of Z-pinned laminates is directly dependent on the strength of the pin–laminate bonding at the interface. In this paper, we investigate novel approaches to the Z-pinning technology in order to increase delamination strength via enhancing mechanical interlocking of the pins. Toward this end, we study the effect of pin insertion at an angle to the vertical in contrast to the conventional vertical pin insertion. Subsequently, a novel variety of pin, namely the threaded pin, is studied as a candidate for reinforcement which increases mechanical interlocking between the pin and the laminate as well as the epoxy-pin contact area, thus delaying delamination. In addition, the effect of anchoring reveals the length of smooth metal pins on to the surface of the laminate before curing on delamination strength is investigated. Experiments performed show increase in tensile pullout strengths when angled, threaded, or anchored pins are used. These experimental results for tensile pullout strengths validate nonlinear finite element models incorporating cohesive zones at the pin–laminate interface. In addition, fracture toughness and delamination resistance under mode-I loading are investigated by performing experiments on double cantilever beam specimens. Results demonstrate the superior delamination resistance properties for angled, threaded, and anchored pin inserts.