The inmate, identified as Charles Henry Bradley, Jr., 38, of Big Stone Gap, reportedly made his escape while being loaded into a transport van with other prisoners at the Wise County courthouse around 3:55 p.m.
Bradley is described as being 5 feet, 9 inches tall and 145 pounds, with brown hair and blue eyes. He was last seen wearing an orange jump suit with a white shirt underneath.
The search for Bradley is being conducted by the Wise County Sheriff's Office and members of the U.S. Marshals Service.
According to a spokeswoman for the Southwest Virginia Regional Jail in Duffield, officers were attempting to load Bradley into a waiting van when he "kicked free of his leg restraints."
Bradley reportedly fled with his handcuffs still intact.
Authorities said anyone who sees Bradley should avoid making contact with him and instead contact the Wise County Sheriff's Office or their local law enforcement agency.
Bradley is considered to be dangerous.
Bradley was being held at the Duffield jail and awaiting trial on charges of abduction, malicious wounding, robbery and conspiracy.
Those charges out of Scott County stem from an alleged home invasion May 25 that took place at a residence near Duffield. According to police reports, Bradley was one of three people arrested for allegedly forcing their way into a 57-year-old man's home before beating and robbing him of medication.
The trio allegedly tied up the victim with a combination of duct tape, wire and tubing before ransacking his home and taking his wallet and an undisclosed amount of medication.
The victim in the alleged invasion was transported to an area hospital where he was treated for several broken bones sustained in the break-in.
Bradley was appearing in court in Wise County on Tuesday for violating probation for a felony offense.
Staff writer Steve Igo contributed to this report.