Favorable conditions allowed the depression to become Tropical Storm Debby early on August 20, and further strengthening into a hurricane occurred 24 hours later.

Debby made three landfalls on August 22, in Barbuda, Saint Barthélemy, and Virgin Gorda, before re-entering the Atlantic north of Puerto Rico.

As Debby moved parallel to the north coast of Hispaniola late on August 23, it weakened back to a tropical storm.

[nb 1] While south of eastern Cuba on August 24, Debby was downgraded to a tropical depression, six hours before completely dissipating.

Light rainfall and gusty winds caused minor damage in Barbuda, Saint Martin, and Trinidad and Tobago.

In Dominican Republic, the Civil Defense Force reported that severe flooding in the northern portions of that country caused the evacuation of more than 700 people.

Impact was lesser in Haiti, where squalls tore tin roofs off of numerous shanty homes and subsequently flooded a few.

At 0000 UTC on August 18, the National Hurricane Center's Tropical Analysis and Forecast Branch (TAFB) indicated a low-level circulation, though the system was still considered "too weak to classify".

[2] In the initial advisory by the National Hurricane Center, the agency noted a large area of convection, weak vertical wind shear, warm sea surface temperatures (SSTs), all of which produced a favorable environment for intensification.

[4] Although the circulation remained relatively disorganized, the central dense overcast (CDO) associated with Debby was large, symmetrical, and had cold cloud tops.

[9] In an advisory issued later that day, the National Hurricane Center noted that although the agency anticipated further strengthening, it would not be "significant" in the short-term, due to Debby's rapid movement west-northwestward and potential land interaction with Hispaniola.

[11] Due to increasing southwesterly wind shear, Debby began to weaken and was downgraded to a tropical storm at 1200 UTC on August 23, while situated north of Dominican Republic.

[2] Beginning late on August 23, it was predicted that Debby would re-strengthen, as SSTs were between 84 and 86 °F (29 and 30 °C) and the storm was anticipated to resume the original west-northwest movement, reducing land interaction.

[12] However, Debby curved westward and continued to become increasingly disorganized, with the low-level circulation being displaced well west of the main, deep convective area.

[2] The National Hurricane Center continued to predict re-intensification, but noted the potential for degeneration into a tropical wave during the next few days in its advisory at 0900 UTC on August 24, due to persistent wind shear.

Elsewhere along the range of the cyclone's predicted path, homes and businesses were boarded up, and families buried emergency supplies in the ground.

Ten United States Navy ships and two submarines off the Coast of Vieques Island temporarily abandoned training exercises and moved over 300 miles (480 km) to the south of Puerto Rico, out of the storm predicted path.

When the hurricane moved into the coastal waters of the U.S. Virgin Islands, the Hovensa oil refinery in St. Croix was shut down, and as a result gas prices rose.

Early on August 21, the hurricane watch was expanded to include the United States Virgin Islands and Puerto Rico.

At 0300 UTC on August 22, a hurricane watch was issued for Haiti north of Port-au-Prince as was a tropical storm warning in Dominican Republic from Palenque to Cabrera.

On August 23, a hurricane warning was issued for the central Bahamas and Cuba in the provinces of Guantanamo, Holguín, and Las Tunas.

[19] Debby was attributed to about $735,000 in damage and 1 indirect fatality, which occurred in Puerto Rico when a man fell off a roof while attempting to remove a satellite dish.

[2][14] Sint Maarten reported little rainfall as the storm almost uneventfully passed over the island, causing mostly minor flooding and vegetation damage.

[24] Feeder bands from Debby affected countries as far south as Trinidad and Tobago, where heavy rainfall resulted in flooding in the Barrackpore region.

[18] The hurricane dropped around 5 inches (130 mm) of rain in San Juan, producing slick roads that resulted in several minor car accidents.

[2] Storm surge damaged about 20 homes and dozens of families were evacuated from Cabrera, Nagua, Río San Juan, and Samaná.

In Nagua, several districts were left without drinking water and electricity after gusts blew down power cables and large trees.

In southern Puerto Plata, flooding in Aguas Negras, Playa Oeste and Dubeau districts forced dozens of families to leave their houses.

In Monte Cristi, heavy rainfall caused flooding in various low-lying districts, with over 200 people affected in the coastal portion of the province.