Mechanoresponsiveness is a ubiquitous feature of soft materials in nature; biological tissues exhibit both strain-stiffening and self-healing in order to prevent and repair deformation-induced damage. These features remain challenging to replicate in synthetic and flexible polymeric materials. In recreating both the mechanical and structural features of soft biological tissues, hydrogels have been often explored for a number of biological and biomedical applications. However, synthetic polymeric hydrogels rarely replicate the mechanoresponsive character of natural biological materials, failing to match both strain-stiffening and self-healing functionality. Here, strain-stiffening behavior is realized in fully synthetic ideal network hydrogels prepared from flexible 4-arm polyethylene glycol macromersviadynamic-covalent boronate ester crosslinks. Shear rheology reveals the strain-stiffening response in these networks as a function of polymer concentration, pH, and temperature. Across all three of these variables, hydrogels of lower stiffness exhibit higher degrees of stiffening, as quantified by the stiffening index. The reversibility and self-healing nature of this strain-stiffening response is also evident upon strain-cycling. The mechanism underlying this unusual stiffening response is attributed to a combination of entropic and enthalpic elasticity in these crosslink-dominant networks, contrasting with natural biopolymers that primarily strain-stiffen due to a strain-induced reduction in conformational entropy of entangled fibrillar structures. This work thus offers key insights into crosslink-driven strain-stiffening in dynamic-covalent phenylboronic acid–diol hydrogels as a function of experimental and environmental parameters. Moreover, the biomimetic mechano- and chemoresponsive nature of this simple ideal-network hydrogel offers a promising platform for future applications.