AbstractFunctionalization of polyolefins, in particular polyisobutylene, remains a relatively unexplored application for the Michael reaction. This work evaluates the potential of polyisobutylene acrylate (PIBA) chain‐end modification via organocatalyzed thiol‐Michael and aza‐Michael additions. A series of chain‐end functional polyisobutylene oligomers are prepared using “click” reactions of thiols or amines to PIBA in the presence of 0.02 equivalents of organocatalyst. Reaction kinetics and chain‐end transformations are monitored using NMR spectroscopy and the macromolecular products are characterized by size exclusion chromatography. Further potential of this synthetic strategy is illustrated by thiol‐Michael addition of thiols formed in situ via nucleophilic thiolactone ring opening. The obtained results provide an efficient method for the preparation of functional polyisobutylene oligomers that can be utilized in a broad range of potential applications.