The bypass of an air bubble through a liquid−liquid interface may produce rich fluidic physics. Air injection is a passive technique to mix the contents of the two separated fluids and provides an effective heat and mass transfer intensification by increasing the interfacial area between them. Entrainment of heavier fluid into the lighter fluid at atmospheric and isothermal conditions has been simulated by using the VOF (volume of fluid) technique mimicking a Taylor bubble bypass through a horizontal liquid−liquid interface of water and polydimethylsiloxane (PDMS) solution. The migration of a Taylor bubble across the interface is completed through five different stages, namely, approach, encapsulation, de-encapsulation, entrainment, and detrainment. The bubble kinematics, entrained water volume, microdroplets formation, and film thinning characteristics have been studied in detail. The marginal pinch-off mechanism for the rupturing of the entrapped water film has been observed due to the presence of the surface tension gradient. The film thinning initially occurs due to the domination of gravitational force and eventually due to capillary force after the entrapped film thickness achieves capillary length scale, δ crit ∼ (σ/(ρg)) 1/2 . The entrapped water film shrinks over the interface of the Taylor bubble to generate the water microdroplets in the PDMS solution. The entrained height and volume of the water column grows quadratically with time.