Well-performing subsurface drainage systems form an important aspect of pavement design by the Iowa Department of Transportation (DOT). The recently completed Iowa Highway Research Board (IHRB) project TR-643 provided extensive insights into Iowa subsurface drainage practices and pavement subdrain outlet performance. However, the project TR-643 (Phase I) forensic testing and evaluation were carried out in a drought year and during the fall season in 2012. Based on the findings of IHRB Project TR-643, the Iowa DOT requested an expanded Phase II study to address several additional research needs: evaluate the seasonal variation effects (dry fall 2012 versus wet spring/summer 2013, etc.) on subdrain outlet condition and performance; investigate the characteristics of tufa formation in Iowa subdrain outlets; investigate the condition of composite pavement subdrain outlets; examine the effect of resurfacing/widening/rehabilitation on subdrain outlets (e.g., the effects of patching on subdrain outlet performance); and identify a suitable drain outlet protection mechanism (like a headwall) and design for Iowa subdrain outlets based on a review of practices adopted by nearby states. A detailed forensic test plan was developed and executed for inspecting the Iowa pavement subdrains in pursuit of fulfilling the Phase II study objectives. The observed outlets with blockage and the associated surface distresses in newly constructed jointed plain concrete pavements (JPCPs) were slightly higher during summer 2013 compared to fall 2012. However, these differences are not significant. Less tufa formation due to the recycled portland cement concrete (RPCC) base was observed with (a) the use of plastic outlet pipe without the gate screen–type rodent guard and (b) the use of blended RPCC and virgin aggregate materials. In hot-mix asphalt (HMA) over JPCP, moisture-related distress types (e.g., reflection cracking) were observed more near blocked drainage outlet locations than near “no blockage” outlet locations. This finding indicates that compromised drainage outlet performance could accelerate the development of moisture-related distresses in Iowa composite pavement systems.