Dam sites provide an outstanding opportunity to explore dynamic changes in the groundwater flow regime because of the high hydraulic gradient rapidly induced in their surroundings. This paper investigates the temporal changes of the hydraulic conductivities of the rocks and engineered structures via a thorough analysis of hydrological data collected at the Dokam Dam, Iraq, and a numerical model that simulates the Darcian component of the seepage. Analysis of the data indicates increased seepage with time and suggests that the hydraulic conductivity of the rocks increased as the conductivity of the grout curtain decreased. Conductivity changes on the order of 10−8 m/s, in a 20-yr period were quantified using the numerical analysis. It is postulated that the changes in hydraulic properties in the vicinity of Dokan Dam are due to suspension of fine materials, interbedded in small fissures in the rocks, and re-settlement of these materials along the curtain. Consequently, the importance of the grout curtain to minimize the downstream seepage, not only as a result of the conductivity contrast with the rocks, but also as a barrier to suspended clay sediments, is demonstrated. The numerical analysis also helped us to estimate the proportion of the disconnected karstic conduit flow to the overall flow.