A new biobased bismaleimide architecture from methyl oleate, consisting of an aliphatic branched structure, denoted methyl oleate bismaleimide (MO BMI), was synthesized and fully characterized. MO BMI was used as a cross-linking agent to obtain networks by using linear biobased furan bearing PUs via the Diels-Alder reaction and compared with more conventional aromatic or aliphatic bismaleimides (BMIs). These networks can be defined as dissociative covalent adaptable networks (CANs). Different linear biobased PUs were synthesized by using rapeseed-based polyol, hexamethylene diisocyanate, and (furan-2,5-diyl)dimethanol as a chain extender. The furan content was controlled by varying the hard segment content. Compared to conventional BMIs, MO BMI as biobased cross-linker impacts particularly the materials performance and the mechanical properties, for example an increase of the elasticity. MO BMI also yields most consistent advanced properties in terms of thermal recyclability and self-healing.