A deep upper level trough was in place across the central U.S. on this day. This translated down to the surface as well, with strong SW flow in place across much of Ohio Valley. Meanwhile, a cold front, extending from a occluded low pressure system in southeast Canada, was located just ahead of the trough, being pushed eastward with the upper level flow. During the first part of the day on the 17th, this front was located NW of the state, making its way eastward. By the afternoon and evening hours, it began to push into Kentucky, developing a secondary low pressure system. This low continued to gain strength, traversing eastern KY, along with the surface cold front, through the late evening and first part of the overnight.
At 21Z on the 17th, the radar showed rain increasing across eastern KY ahead of this powerful cold front. An intensifying 70 to 80kt 850mb jet was analyzed just ahead of the boundary, which combined with some downslope drying, to produce strong to damaging wind gusts across portions of eastern Kentucky. A wind advisory and high wind warning were in effect for all of eastern Kentucky through the evening and into the first part of the overnight given the conditions. Gradient winds were the culprit for multiple trees down across eastern Kentucky, specifically in Clay, Floyd, Harlan, and Perry counties.
Aside from the intense gradient winds, strong to severe storms also develop along and just ahead of the actual cold front as it moved through. These storms helped to translate the higher winds aloft down to the ground, resulting in multiple reports of wind damage across Powell and Estill Counties.
The event ended up being centered around wind damage, both gradient and convective, all ending just after the front passed through and exited eastern KY by 6Z on the 18th.

High Wind in CLAY, KENTUCKY
From 17-FEB-22 22:45:00 to 17-FEB-22 23:00:00 (EST-5)
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 4.00K
Reported by: Department of Highways

The Highway Department reported multiple trees down across the county between 10:45pm and 11pm EST. Roads impacted by downed trees included KY-421 near the Boho community, KY-638 near the Sidell community, KY-11 near the community of Tanksley, and KY-3477 near US-421 just SSE of the Fall Rock community.

High Wind in HARLAN, KENTUCKY
From 17-FEB-22 23:43:00 to 18-FEB-22 00:05:00 (EST-5)
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 4.00K
Reported by: Department of Highways

The Highway Department reported multiple trees down across the county between 11:43pm and 12:05am EST. Roads impacted by downed trees included KY-221 between the intersection with Evelyn Lane and Mill Branch Church Loop, KY-1780 between the intersections with Salt Trace Branch Road and Middle Fork Road, KY-990 near the intersection with Engle Road, and KY-987 just east of the intersection with Laurel Branch.

High Wind in FLOYD, KENTUCKY
From 17-FEB-22 23:45:00 to 17-FEB-22 23:45:00 (EST-5)
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: Department of Highways

The Highway Department reported a tree down due to high winds along KY-76, near the intersection with KY-899.

High Wind in PERRY, KENTUCKY
From 17-FEB-22 23:22:00 to 17-FEB-22 23:30:00 (EST-5)
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 2.00K
Reported by: Department of Highways

The Highway Department reported two trees down across the county between 11:22pm and 11:30pm EST. Roads impacted by downed trees included Francis Branch Road near the community of Ned, and KY-28 between mile markers 13 and 14.

High Wind in ESTILL, KENTUCKY
From 17-FEB-22 19:00:00 to 17-FEB-22 19:00:00 (EST-5)
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: Department of Highways

The Highway Department reported a tree down due to high winds on Red Lick Road, near the intersection with Station Camp Road.

Thunderstorm Wind in ESTILL, KENTUCKY
From 17-FEB-22 19:38:00 to 17-FEB-22 19:38:00 (EST-5)
Location: NORTH IRVINE
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: 911 Call Center

A tree was reported down on Mountain Crest Circle near the intersection with Grindstone Road in North Irvine.

Thunderstorm Wind in ESTILL, KENTUCKY
From 17-FEB-22 19:24:00 to 17-FEB-22 19:24:00 (EST-5)
Location: RICE STATION
Magnitude: 50.00 EG
Property damage: 1.00K
Crop damage: 0.00K
Reported by: 911 Call Center

A car port was reported having been blown over onto Richmond Road near the intersection with Pea Ridge Road.

Thunderstorm Wind in POWELL, KENTUCKY
From 17-FEB-22 19:24:00 to 17-FEB-22 19:24:00 (EST-5)
Location: VAUGHNS MILL
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: 911 Call Center

Dispatch reported that a tree was down on Hardwicks Creek Road near the community of Vaughns Mill.

Thunderstorm Wind in POWELL, KENTUCKY
From 17-FEB-22 19:30:00 to 17-FEB-22 19:30:00 (EST-5)
Location: NATURAL BRIDGE
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: 911 Call Center

A tree was reported down on Natural Bridge Road near Natural Bridge State Park.

Thunderstorm Wind in POWELL, KENTUCKY
From 17-FEB-22 19:30:00 to 17-FEB-22 19:30:00 (EST-5)
Location: ROSSLYN
Magnitude: 50.00 EG
Property damage: 0.00K
Crop damage: 1.00K
Reported by: 911 Call Center

A tree was reported down on Cane Creek Road, near the community of Rosslyn.