An axially chiral N,N′-bisindole is shown on the cover picture, representing one of the fruits on the tree of chiral indole chemistry. In their Research Article (e202300419), Yu-Chen Zhang, Feng Shi, and co-workers describe the organocatalytic enantioselective construction of the axially chiral N,N′-bisindole scaffold with promising applications in medicinal chemistry and asymmetric catalysis.