The Winston Tunnel regularly needed repairs during its 84-year history. Ever-present ground water continually deteriorated the tunnel materials and the shale rock surrounding the bore. In 1912, the west portal was extended 60 feet with a non-reinforced concrete arch section backfilled with stone and in 1918, a 12 inch plain concrete floor was added to the tunnel. The replacement floor was twice as thick as the concrete floor added in 1902. New steel rails and wood ties were also added to a foot of ballast in the tunnel and approaches. These repairs were engineered to improve drainage in the tunnel. In 1944 and 1947, two sections of the tunnel totaling 1,266 feet from the east portal were reconstructed with 8 inch steel ribs set in concrete added flush to the walls and arch. A smaller section of 200 feet near the west portal was also reconstructed using the same materials. The steel rib and concrete lining replaced sections of the brick and concrete lining added in 1902