During the period between June 26 to 28, southern Indiana and central Kentucky were in an area of weak surface high pressure. The atmosphere was moist with little shear but  decent instability.
On June 27th, a well defined large mesoscale convective vortex formed over Missouri and moved east. Out ahead of this system storms initiated from diurnal heating. Between this system and diurnal afternoon / evening thunderstorm activity, widespread storm damage and flooding was reported during the June 26-28 period.

Thunderstorm Wind in OHIO, KENTUCKY
From 26-JUN-19 19:06:00 to 26-JUN-19 19:06:00 (CST-6)
Location: CROMWELL
Magnitude: 52.00 EG
Crop damage: 0.00K
Reported by: Public

One tree was reported down on Highway 231 just before Cromwell Market.

Thunderstorm Wind in BUTLER, KENTUCKY
From 26-JUN-19 18:04:00 to 26-JUN-19 18:04:00 (CST-6)
Location: DEXTERVILLE
Magnitude: 52.00 EG
Crop damage: 0.00K
Reported by: Emergency Manager

A tree was reported down at Possum Hollow in Morgantown, Kentucky.

Thunderstorm Wind in OHIO, KENTUCKY
From 26-JUN-19 19:02:00 to 26-JUN-19 19:02:00 (CST-6)
Location: ROSINE
Magnitude: 52.00 EG
Crop damage: 0.00K
Reported by: 911 Call Center

Ohio County Dispatch reported a tree down on Highway 62 just before Rosine.

Thunderstorm Wind in CLINTON, KENTUCKY
From 27-JUN-19 16:03:00 to 27-JUN-19 16:03:00 (CST-6)
Location: HIGHWAY
Magnitude: 55.00 EG
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Dispatch reports a couple of trees down along Highway 1590 near Hay Road and Highway 1351.

Thunderstorm Wind in ADAIR, KENTUCKY
From 27-JUN-19 17:30:00 to 27-JUN-19 17:32:00 (CST-6)
Location: OZARK
Magnitude: 52.00 EG
Crop damage: 0.00K
Reported by: Public

Tree were reported down along Highway 80.

Flash Flood in OHIO, KENTUCKY
From 26-JUN-19 21:51:00 to 26-JUN-19 23:51:00 (CST-6)
Location: HAYNESVILLE
Flood cause: Heavy Rain
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Flash flooding was reported over Highway 69 near Fordsville, Kentucky.

Flash Flood in OHIO, KENTUCKY
From 26-JUN-19 21:58:00 to 26-JUN-19 23:00:00 (CST-6)
Location: HORTON
Flood cause: Heavy Rain
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Flash flooding was reported near the intersection of Vinehill Road and Highway 62.

Flash Flood in OHIO, KENTUCKY
From 26-JUN-19 22:01:00 to 26-JUN-19 23:31:00 (CST-6)
Location: ROB ROY
Flood cause: Heavy Rain
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Roads were closed near the intersection of Bald Knob Road and Rob Roy Road due to flooding.

Flash Flood in LOGAN, KENTUCKY
From 26-JUN-19 23:00:00 to 26-JUN-19 23:59:00 (CST-6)
Location: AUBURN
Flood cause: Heavy Rain
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Flash flooding was reported along East Main Street in Auburn, Kentucky.

Flash Flood in LOGAN, KENTUCKY
From 26-JUN-19 23:44:00 to 27-JUN-19 02:00:00 (CST-6)
Location: BEECHLAND
Flood cause: Heavy Rain
Property damage: 0.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Beechland - Quality Road was closed due to flash flooding.

Thunderstorm Wind in SIMPSON, KENTUCKY
From 26-JUN-19 17:33:00 to 26-JUN-19 17:33:00 (CST-6)
Location: MIDDLETON
Magnitude: 55.00 EG
Crop damage: 0.00K
Reported by: Emergency Manager

Two 40 foot trees fell down, one was hollow and one was healthy, on the 2900 block of Middleton Road.

Thunderstorm Wind in SIMPSON, KENTUCKY
From 27-JUN-19 17:52:00 to 27-JUN-19 17:52:00 (CST-6)
Location: FRANKLIN
Magnitude: 53.00 EG
Crop damage: 0.00K
Reported by: Emergency Manager

A large tree was down on Main Street and Kentucky Avenue.

Thunderstorm Wind in SIMPSON, KENTUCKY
From 27-JUN-19 17:52:00 to 27-JUN-19 17:52:00 (CST-6)
Location: STOWERS
Magnitude: 54.00 EG
Crop damage: 0.00K
Reported by: Emergency Manager

A large tree fell down on Kentucky 73 / Morgantown Road.

Thunderstorm Wind in SIMPSON, KENTUCKY
From 27-JUN-19 18:00:00 to 27-JUN-19 18:05:00 (CST-6)
Location: FRANKLIN
Magnitude: 53.00 EG
Property damage: 15.00K
Crop damage: 0.00K
Reported by: 911 Call Center

Multiple trees and power lines came down around Franklin, KY.

Thunderstorm Wind in WARREN, KENTUCKY
From 27-JUN-19 18:02:00 to 27-JUN-19 18:02:00 (CST-6)
Location: WOODBURN
Magnitude: 50.00 EG
Crop damage: 0.00K
Reported by: Broadcast Media

Several large tree branches came down in Woodburn, Kentucky.

Thunderstorm Wind in LOGAN, KENTUCKY
From 27-JUN-19 18:17:00 to 27-JUN-19 18:17:00 (CST-6)
Location: RUSSELLVILLE
Magnitude: 52.00 EG
Crop damage: 0.00K
Reported by: 911 Call Center

A tree fell down on Baker Nature Trail.

Thunderstorm Wind in WARREN, KENTUCKY
From 27-JUN-19 18:27:00 to 27-JUN-19 18:27:00 (CST-6)
Location: BOWLING GREEN
Magnitude: 53.00 EG
Property damage: 20.00K
Crop damage: 0.00K
Reported by: 911 Call Center

A tree and power lines came down along the 400 block of West 12th Avenue.

Thunderstorm Wind in SCOTT, KENTUCKY
From 28-JUN-19 18:06:00 to 28-JUN-19 18:08:00 (EST-5)
Location: OXFORD
Magnitude: 53.00 EG
Crop damage: 0.00K
Reported by: Public

Trees were reported down northeast of Georgetown, Kentucky.

Thunderstorm Wind in HARRISON, KENTUCKY
From 28-JUN-19 18:15:00 to 28-JUN-19 18:15:00 (EST-5)
Location: CYNTHIANA
Magnitude: 50.00 EG
Crop damage: 0.00K
Reported by: Public

A tree was reported down in Cynthiana, Kentucky.