A copper(I)-catalyzed click-crosslinking approach between star-shaped poly(isobutylene)s (PIBs) suitable for self-healing applications has been investigated. The kinetics has been studied in dependence on the functional group density and autocatalysis was observed. The so developed crosslinking approach has been extended to hyperbranched PIBs. Thus, improved network densities were envisioned while tuning the molecular architecture. Click-crosslinking resulted in strongly crosslinked polymeric materials within 30 to 50 minutes emphasizing its great potential for the development of self-healing polymers. Accordingly, the click-crosslinking approach was combined with a multiple healing concept based on supramolecular cluster formation. Therefore, four arm star PIBs functionalized with azide- and thymine-endgroups have been prepared enabling the design of a multiple time self-healing system based on dual network formation due to supramolecular cluster formation and click-crosslinking.