The two had a conversation about a variety of subjects such as NBA free agency, Armstead's basketball skills and how the defensive lineman chose to play college football at the University of Oregon.
During their livestream, Armstead also unveiled one of his hidden talents: chess.
Armstead started playing virtual chess games on Chess.com and used it as a way to keep in contact with former 49ers defensive coordinator Robert Saleh, now head coach of the New York Jets.
"I've got four wins and he's got about 14," Armstead said. "That's how we stay connected, just playing chess throughout the season. It gets competitive, we have a little rivalry."
Since joining Chess.com in 2018, Armstead has played over 2,300 games against "master level" bots, people from across the world and even the 49ers Faithful. Playing under the username, ARIK916, Armstead has won 12 of his last 20 games on the site.
"I've definitely learned a lot over the past year and a half," Armstead said. "I've gotten a lot better, for sure... It's definitely addictive, my wife gets mad at me. That's like what I do like before I go to sleep."
Earlier this month, Armstead was a contestant in the 2022 Chess.com BlitzChamps Consolation Bracket, an NFL-themed tournament featuring chess-playing football stars with a $100,000 prize fund dedicated to the players' desired charities.
Armstead was scheduled to match up against Cleveland Browns wide receiver Amari Cooper, Cincinnati Bengals cornerback Chidobe Awuzie, New York Giants defensive end Kayvon Thibodeaux, former Arizona Cardinals wide receiver Larry Fitzgerald and former Miami Dolphins third-round pick Will Davis.
Although Armstead was unable to play the consolation bracket match against Thibodeaux due to a personal matter, the players agreed to split the $22,500 consolation prize fund equally between their charities in spite of the match not taking place.
Awuzie took first place in the BlitzChamps chess bracket earning $25,000 towards his charity, the Awuzie Kickstep Foundation, and Armstead walked away with $11,250 in charity proceeds for his foundation, the Armstead Academic Project.