Unique boiling behavior at near-critical conditions can leverage the large heat transfer coefficients associated with flow boiling while mitigating some of the disadvantages encountered in two-phase flows, presenting opportunities for enhancing the stability and effectiveness of cooling systems. Contemporary understanding treats subcritical boiling and supercritical heat transfer as two distinct regimes, separated by the critical point. Recent studies investigating microchannel flow boiling near the critical point challenge this notion, suggesting a significant alteration in subcritical phase change heat transfer mechanisms, predominantly driven by variations in thermophysical properties near the critical point. However, a generalized understanding of heat transfer behavior and the phase change physics near the critical point is lacking. The current work presents a new perspective to elucidate underlying fluid phenomena associated with near-critical (0.85<PR<1.02) microscale (Dh=500μm) phase change over parameterized experimental conditions (G=100−1000kgm−2s−1; q″=2−100Wcm−2). Through high-speed (8000fps) side-view microscopic imaging and simultaneous heat transfer measurements, unique flow behavior was discovered at PR>0.95, including supercritical-like phenomena and evidence of homogeneous nucleation which form the physical basis for altered heat transfer behavior. The visualized flow physics and heat transfer behavior suggest a continuous transition from subcritical phase change to supercritical mechanisms near the critical point. As homogeneous nucleation becomes the dominant phase change mechanism, the near-wall heat transfer condition transitions from nucleate boiling to single-phase vapor convection. However, due to significant thermophysical property variations near the critical point, this single-phase convection condition exhibits fluid physics and heat transfer behavior virtually indistinguishable from supercritical conditions. These insights significantly disrupt the conventional understanding of a sharp transition in fluid behavior at the critical point. The gradual change in flow boiling mechanisms near the critical point presents opportunities for application-specific tuning of heat transfer performance through pressure variation alone.