Strigolactones (SLs) are a class of signalling molecules secreted by the roots of plants into the rhizosphere. On the one hand, they serve as the signal for recruiting arbuscular mycorrhizal fungi which have a symbiotic relationship with plants. On the other hand, they are also host detection signals for the non-symbiotic, pathogenic, root parasitic plants, which use the SLs as germination stimulants. Finally, recently the SLs were discovered to be a new class of plant hormones that regulate processes such as branching/tillering and root architecture. Intriguingly, >25 different SLs have already been discovered that all have the so-called D-ring but otherwise display many differences in structure and functional groups. In this review, we will critically discuss the structural diversity in the SLs. How are they synthesized in plants; how has this structural diversity possibly evolved; what is the biological relevance of this diversity; and what does this imply for the perception of the SLs by receptors in the plant itself and in other organisms? Finally, we conclude that only little is known about the biological significance of this structural diversity, and we will give an outlook on how to elucidate their importance further.