After being classified as a subtropical cyclone, Olga kept an organized outflow, and located to the southeast of a strong ridge over the western Atlantic Ocean, the cyclone moved west-southwestward. The storm strengthened a little bit while moving along the northern coast of Puerto Rico, and after an increase in convection near the center, Olga made landfall near Punta Cana, Dominican Republic at 1800 UTC on December 11. A Hurricane Hunters flight into the storm reported peak winds of 60 mph (95 km/h), and on December 12, the National Hurricane Center reclassified Olga as a tropical cyclone while it was still inland. Convection quickly weakened as the storm crossed central Hispaniola, and after reaching the Caribbean Sea the system lacked the convection required for the classification of a tropical cyclone; rainbands well to its northeast had stronger winds, though the center became very disorganized with dry air and strong wind shear. Late on December 12, convection increased a little bit over the center, though by that time the cyclone weakened to tropical depression status. As a certain amount of convection failed to exist, the National Hurricane Center discontinued advisories on Olga earlier on December 13 while located about 80 miles (130 km) northwest of Kingston, Jamaica. Its remnants continued west-northwestward with a clear low-level circulation, creating scattered thunderstorms over Cuba and the Cayman Islands with its moisture extending northward into southern Florida.