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Rogers Media hired Armstrong as an analyst for Sportsnet's national coverage of the NHL starting in the 2014–15 season. Since 2016, he has also been an analyst of Pittsburgh Penguins games for the AT&T SportsNet Pittsburgh post-game broadcast crew.

On July 27, 2013, Armstrong left the NHL as a free agent and signed his first and only European contract with the Växjö Lakers of the Swedish Hockey League.

With the opening of free agency the next day, July 1, 2012, Armstrong signed a one-year, $1 million contract with the Montreal Canadiens. During the lock-out-shortened 2012–13 season, Armstrong played mostly on the fourth line. Although he contributed only 5 points in 37 games, Montreal made the 2013 playoffs.

On July 1, 2010, Armstrong signed as an unrestricted free agent with the Toronto Maple Leafs on a three-year, $9 million contract. With his first two seasons largely affected by injury and inconsistent play, on June 30, 2012, he was bought-out by the Maple Leafs from his final season of his contract.

On July 16, 2009, Armstrong re-signed with the Thrashers to a one-year, $2.4 million contract. He served as one of the team's alternate captains during the 2009–10 season.

Armstrong had three overtime goals for the Penguins in the 2006–07 season, beating Kari Lehtonen of the Atlanta Thrashers, Ed Belfour of the Florida Panthers and Henrik Lundqvist of the New York Rangers. The Penguins and Armstrong avoided an arbitration hearing in the 2006–07 off-season by re-signing him to two-year, $2.2 million contract. Armstrong became very close friends with former teammate Sidney Crosby while playing for the Penguins. On January 1, 2008, Armstrong scored the first ever outdoor Winter Classic goal in the inaugural event.

Pittsburgh traded Armstrong on February 26, 2008, to the Atlanta Thrashers, alongside Angelo Esposito, Erik Christensen and a first-round draft pick, in exchange for Marián Hossa and Pascal Dupuis. He then scored 11 points in 18 games to finish out the 2007–08 season with Atlanta.

Armstrong was a member of Canada's 2007 IIHF World Championship-winning team. His only goal of the tournament was the game-winning goal in the gold medal game against Finland in Moscow, which Canada won 4–2. He scored the first ever outdoor Winter Classic goal in the inaugural 2008 event.

In the 2005–06 season, Armstrong made his NHL debut, and had a superb rookie season, in which he played 47 games and tallied 40 points (16 goals and 24 assists) and had a team-high plus-minus rating of +15.

Armstrong was drafted by the Pittsburgh Penguins in the first round of the 2001 NHL Entry Draft as the 21st pick overall.

Colby Joseph Armstrong (born November 23, 1982) is a Canadian former professional ice hockey player who played in the National Hockey League (NHL) for the Pittsburgh Penguins, Atlanta Thrashers, Toronto Maple Leafs and Montreal Canadiens in a 9-year career. He currently serves as an NHL analyst for Sportsnet. Armstrong's younger brother, Riley briefly played in the NHL, with the San Jose Sharks.