On February 11, 2019, Conklin signed with Piratas de Quebradillas for the 2019 BSN season, returning to the club for a second stint. On April 12, 2019, he was released by Quebradillas and signed with Indios de Mayagüez for the rest of the season. In 14 games for Quebradillas, he averaged 15.6 points, 5.5 rebounds and 1.7 assists. In July 2019, he was named BSN MVP and to the BSN All-Star team.
