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Homo and copolymerization of isoprene (IP) with small amounts (1% wt) of glycidyl methacrylate) were conducted using the reversible addition‐fragmentation chain‐transfer process (RAFT) at 125 °C in a solution polymerization process using toluene as solvent. Suitable reaction conditions to avoid Diels–Alder dimerization of IP and crosslinking were determined; and 4‐cyano‐4‐[(dodecylsulfanylthiocarbonyl)sulfanyl] pentanoic acid was found to be the best transfer agent among those tested. Theoretical calculations were used to understand why some RAFT agents work better than others in these polymerizations. Molecular weights M_n higher than 100,000 Da were reached by successive chain extension experiments, confirming the livingness of the intermediate polymers. All the successful polymerizations yielded average molar masses (M_n) of about 75% compared to the theoretical M_n (M_n,theo) depending on …