The island of Martinique received a record 12 inches (300 mm) of rain over a 24-hour period, causing severe river flooding throughout northern villages and communes.

Over the following days, the wave tracked steadily west-northwestward across the tropical Atlantic while retaining a distinct cloud pattern on satellite images.

[1][2] Steered by a mid- to low-level wind flow, the depression continued west-northwest toward Martinique,[1] decelerating in reaction to the island's northern mountain range.

[3] Satellite images on the afternoon of August 14 showed the development of a central dense overcast, as greater atmospheric turbulence over the rugged terrain amplified the cyclone's convection;[1][3] the next reconnaissance flight revealed that wind speeds near the center had increased to gale force.

Based on these observations, the NHC upgraded the depression to Tropical Storm Cindy around 18:00 UTC, at which time the cyclone was located over Martinique with winds of 40 mph (65 km).

[1] Over the course of August 15, Cindy's cloud pattern remained disorganized due to unfavorable wind shear; the center of circulation became ill-defined, with the strongest thunderstorms confined to the eastern portion of the cyclone.

[4][5] Despite the unfavorable conditions, the storm managed to strengthen marginally on August 16, attaining peak winds of 45 mph (72 km/h) and a minimum pressure of 1007 mbar (hPa; 29.74 inHg), roughly 85 mi (137 km) southeast of Santo Domingo.

[9] Officials issued flash flood warnings for parts of the island, and about 600 people living in flood-prone areas sought shelter ahead of the storm.

[3] The greatest quantities fell to the northeast of a line between Sainte-Marie and Fort-de-France, with day totals of more than 4 in (100 mm) recorded at every weather station in that region.

Large amounts of volcanic matter from the riverbed congealed into a massive debris flow, which struck the small commune of Le Prêcheur.

[36] Farther south, a combination of torrential rainfall and poor storm drains resulted in flood damage to private property and an aquafarm in Le Morne-Vert.

[38] Unseasonable sea conditions in Cindy's wake hindered local fishers from selling their catch to trading vessels in Petite Martinique.

In Guadeloupe, the storm dropped rain across southern Basse-Terre Island through August 14–15; a peak total of 9.02 in (229 mm) was recorded at the summit of La Grande Soufrière.

[41] A moderate breeze with 28 mph (45 km/h) gusts brushed Dominica, and 1.25 in (32 mm) of rain fell at Canefield Airport within 24 hours of Cindy's passage.

[13][14] In Villa Altagracia, one fatality occurred when a child drowned in flood waters; the final death toll for the country stood at two.