After its formation, the depression gradually became better organized; the NHC upgraded it to Tropical Storm Lenny on November 14, based on reports from the Hurricane Hunters. When it was first upgraded to a tropical storm, the cyclone already had winds of and a developing eye feature. At 0000 UTC on November 15, Lenny attained hurricane status about southwest of Kingston, Jamaica. The quick intensification was unexpected and occurred after a large area of convection blossomed over the center. At the same time, Lenny developed an anticyclone aloft, which provided favorable conditions for the hurricane's development. After moving east-southeastward during its initial development stages, the hurricane turned more to the east on November 15. The Hurricane Hunters reported winds of , which indicated that Lenny had become a Category 2 on the Saffir-Simpson Hurricane Scale. However, the cloud pattern subsequently became less organized as the eye disappeared, and Lenny's winds weakened to while the hurricane passed south of Hispaniola. The NHC noted the deterioration could have been due to a disruption of the storm's small inner core by "subtle environmental changes". After the sudden weakening, the Hurricane Hunters reported that the eye had reformed and the hurricane's winds had reached . At the time, a ridge was expected to build to Lenny's east and turn the storm northeastward into Puerto Rico 24 hours later.