Countercurrent spontaneous imbibition is one of the most significant mechanisms for the mass transfer between fractures and matrixes in tight reservoirs. Adding surfactants and pressurization are two common methods to enhance the imbibition. In this study, we used the low-field nuclear magnetic resonance (NMR) instrument to monitor the dynamic imbibition processes with surfactants added and fluid pressure applied. The T2 relaxation distribution and corresponding water saturation profiles during the imbibition process were obtained by analyzing NMR responses. We found that sodium alpha-olefin sulfonate (AOS) could improve the oil recoveries of laboratory-scale cores to 22.31 and 29.59% with different concentrations (0.1 and 0.5 wt%). The surfactant addition not only expands the imbibition area, but also reduces the residual oil saturation in the imbibition profile. However, the actual maximum imbibition distances are only approximately a centimeter long (0.9412 and 1.1372 cm), which is insignificant for field scale. Due to the minimal imbibition distance, high-quality hydraulic fracturing is required to generate a large number of fractures for imbibition to ensure considerable oil recovery at the field scale. In addition, surfactant is consumed during spontaneous imbibition of oil-wet rocks and increasing surfactant concentration facilitates the imbibition process. However, arbitrarily increasing the concentration does not achieve the expected oil recovery because of the high adsorption capacity resulting from the high concentration. We need to consider economic efficiency to optimize a reasonable surfactant concentration. It was found that traditional dimensionless scaling models are not applicable in the complicated surfactant-enhanced imbibition. Hence, we proposed a new scaling group for scaling laboratory date to the field in fractured oil-wet formations. Moreover, we compared the imbibition process under different pressure conditions (7.5 and 15 MPa) and found that the effect of fluid pressure on countercurrent imbibition is not obvious.