This study employed computational methods to elucidate the influence of structural features on the cyclization pathways of 1,5-diynes through the 5-endo-dig and 6-endo-dig mechanisms. The results revealed that the nature of the central linker played a significant role in dictating the preferred cyclization pathway. Notably, the capacity of this linker to extend delocalization appears to be the key factor governing the reaction pathway preference.