Over time, oil consumption has increased along with a continuous demand for petroleum products that require finding ways to increase hydrocarbon production more economically and effectively. So, enhanced oil recovery technologies are believed to be very promising and will serve as a key to meeting the future energy demand. This paper aims to introduce an innovative method to boost the EOR by using two novel types of surfactants synthesized from sulfonamide derivatives. Types I and II surfactants were analyzed using Fourier transform infrared spectroscopy, and their characterization was further performed using 1H NMR and 13C NMR spectroscopy. Additionally, the evaluation of these surfactants included interfacial tension measurements at concentrations up to 0.9 wt %. The combination of types I and II surfactants with alkaline (NaOH) was also investigated by the measurements of interfacial tension. A series of coreflood and sandpack tests under high-salinity conditions were carried out to assess the effects of a surfactant alone and alkaline-surfactant as a combination on improving oil recovery. The rock wettability was evaluated using relative permeability saturation curves, and the oil displacement efficiency was determined using fractional flow curves. The coreflood results demonstrated that alkaline-surfactant flooding with the chemical formula 0.2 wt % surfactant type II plus 0.5 wt % NaOH achieved a higher oil recovery of 74% OOIP compared to surfactant flooding with the chemical formula 0.5 wt % surfactant type II (64% OOIP) and waterflooding (saline solution with a 35,000 ppm salinity: 48% OOIP). Moreover, the experimental results showed that under both core and sandpack flood conditions, there was a noticeable reduction in oil-water interfacial tension, a change in rock wettability to more water-wet, and higher efficiency of oil displacement when alkaline was added to the surfactant. Based on current research, the alkaline-surfactant formulation is strongly recommended for chemical flooding because of its high efficacy and relatively low cost.