In the 2016–17 NHL season, Sheary continued to play alongside Sidney Crosby for the entire year, getting 23 goals and 30 assists for 53 points. Sheary got his first 3-point game on January 16, 2017, against the Washington Capitals. The Penguins won the game 8–7 in overtime, with Sheary scoring the overtime winner. The Pittsburgh Penguins later went on to win the Stanley Cup, giving Sheary his second Stanley Cup ring.
On July 30, 2017, the Penguins re-signed Sheary to a three-year, $9 million contract worth $3 million annually.
In an interview in November 2017, Sheary admitted that commentators, fans, and players have been mispronouncing his name. His name is pronounced SHARE-ee not SHEER-ee.