On October 11, 2016, Condon was claimed off waivers from the Montreal Canadiens by the Pittsburgh Penguins after being waived the previous day. He would only play one period (20 minutes) in relief for the Penguins before being traded to the Ottawa Senators on November 2 for a fifth-round draft pick in 2017. Condon was acquired due to Senators' starter Craig Anderson facing an uncertain future after his wife was recently diagnosed with cancer, and backup Andrew Hammond being sidelined with an injury.