Things seemed to be looking up when Ryles Chapman moved into his parents' pool house. Ryles had been struggling with an addiction to prescription medications prescribed by his doctor and had participated in rehab programs to fight the addiction. Wes and Jamie Chapman hoped Ryles living in the pool house would be better for him, and it appeared to be working.

On the evening of December 18, 2013, Wes arrived home to find another vehicle parked behind Ryles' vehicle. Worried that one of Ryles' old buddies had stopped by, Wes headed straight to the pool house, only to find that Ryles had locked the door and blocked it by pulling out a cabinet drawer.

Wes could see Ryles and tried talking to him, but Ryles bolted from the house in his boxer shorts, leaving the rest of his belongings - including his wallet and money, keys, and cellphone - behind. They later found out that Ryles had quit his job that same morning and cashed his last check, even though he didn't take it with him.

Shortly after Ryles ran out of the house, he was seen by a family friend at the entrance of the Bocage subdivision where the Chapmans lived. At the time, the person thought Ryles was just out for a jog and didn't think much about it.

Early on, authorities stated "the circumstances surrounding Chapman's disappearance make it different than other missing persons cases," but they didn't elaborate on what exactly was different.

In 2017, Wes told The Dothan Eagle he felt Ryles was alive and just not wanting to make contact. He stated cell phone records indicated Ryles' old cell phone had been used "up north" and a fellow classmate had seen Ryles at Club La Vela in Panama City, FL.

Multiple searches have been conducted, but none of the searches lead to Ryles. Law enforcement also conducted nearly two dozen polygraph tests on friends and family, but no leads were established. While numerous people have claimed to have seen Ryles over the years, but those sightings have either been ruled out or unconfirmed.