This study evaluated the technical feasibility of implementing a subsurface drainage system in 1000 ha of undrained agricultural land in Aqqala County, Golestan Province, Iran. A monitoring network of 15 observation wells (10 in undrained fields and 5 in an adjacent 3500 ha drained area) was established, and groundwater levels were monitored monthly over one year (February 2025–February 2026). Soil texture was determined from samples collected at three depths, and saturated hydraulic conductivity (Ks) was measured using the inverse auger-hole method. The soils were predominantly fine-textured (clay, silty clay, and clay loam), with low to moderate hydraulic conductivity (0.00045–0.00723 cm s⁻¹), indicating limited permeability and high water-holding capacity. Groundwater remained deeper (in both drained and undrained lands) than 4 m for most of the monitoring period, appearing only in a few wells during the wettest months. Groundwater contour maps showed a relatively uniform water table and a natural hydraulic gradient toward the drained area and the adjacent river. Results showed that constructing a drainage network is not technically justified if the objective is only groundwater control or waterlogging prevention. However, drainage becomes technically feasible when the objective is soil salinity management and productivity improvement. The undrained area had substantially higher soil salinity (8–10 dS m⁻¹) than the drained area (3–5 dS m⁻¹), accompanied by lower wheat yield (2.7 vs. 4.0 t ha⁻¹). Accordingly, subsurface pipe drainage (or deep surface drainage) is recommended for the undrained lands to control salinity, while the existing drainage network should be upgraded to controlled drainage for improved water management under both flood and drought conditions. The novelty of this study lies in distinguishing drainage strategies for groundwater control and salinity management and proposing an integrated management framework based on one year of field observations.