A numerical investigation of the long-time dynamics of two immiscible two-dimensional fluids shearing past one another is presented. The fluids are incompressible and the interface between the bulk phases is subjected to surface tension. The simple case of density and viscosity matched fluids is considered. The two-dimensional Navier–Stokes equations are solved numerically with a fully adaptive nonstiff strategy based on the immersed boundary method. Dynamically adaptive mesh refinements are used to cover at all times the separately tracked fluid interface at the finest grid level. In addition, by combining adaptive front tracking, in the form of continuous interface marker equidistribution, with a predictor–corrector discretization an efficient method is introduced to successfully treat the well-known numerical difficulties associated with surface tension. The resulting numerical method can be used to compute stably and with high resolution the flow for wide-ranging Weber numbers but this study focuses on the computationally challenging cases for which elongated fingering and interface roll-up are observed. To assess the importance of the viscous and vortical effects in the interfacial dynamics the full viscous flow simulations are compared with inviscid counterparts computed with a state-of-the-art boundary integral method. In the examined cases of roll-up, it is found that in contrast to the inviscid flow in which the interface undergoes a topological reconfiguration, the viscous interface remarkably escapes self-intersection and rich long-time dynamics due to separation, transport, and diffusion of vorticity is observed. An even more striking motion occurs at an intermediate Weber number for which elongated interpenetrating fingers of fluid develop. In this case, it is found that the Kelvin–Helmholtz instability weakens due to shedding of vorticity and unlike the inviscid counterpart in which there is indefinite finger growth the viscous interface is pulled back by surface tension. As the interface recedes, thin necks connecting pockets of fluid with the rest of the fingers form. Narrow jets are observed at the necking regions but the vorticity there ultimately appears to be insufficient to drain all the fluid and cause reconnection. However, at another point, two disparate portions of the interface come in close proximity as the interface continues to contract. Large curvature points and an intense concentration of vorticity are observed in this region and then the motion is abruptly terminated by the collapse of the interface.