Anderson would miss parts of the 2016–17 season as he would take personal leave to support his wife in her battle with throat cancer. The Senators would acquire Mike Condon from the Pittsburgh Penguins in exchange for a fifth-round draft pick in the 2017 draft due to both Anderson's personal leave and backup goalie Andrew Hammond being injured at the beginning of the season. On 11 March 2017 Anderson set a team record for most wins by a goaltender when he won his 147th game, breaking the previous record set by Patrick Lalime. In September 2017, Anderson signed a two-year, $9.5 million contract, to begin in the 2018–19 season.