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Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐triazole/triazolium‐based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo‐derived ChB receptors and the halide anions (Cl−, Br−) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis‐bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans‐monodentate receptors. In particular, the telluro‐triazolium‐based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB‐assisted halide abstraction in a Friedel–Crafts alkylation benchmark reaction. [ABSTRACT FROM AUTHOR]