"It took me right back to that place again," Bryant said after practice Tuesday.
Bryant ruptured his left Achilles in April 2013, costing him the rest of that season. Henry had surgery Tuesday to repair his Achilles, which will cost him the rest of this one.
Henry's injury occurred during a non-contact drill in Monday's practice.
"It was just like mine, same thing," Bryant said. "[He] just tried to take off, drive to the basket and it just popped."
Since the injury, Bryant said, he's been in close contact with Henry, who averaged 2.2 points per game in nine appearances this season.
"Just trying to keep him positive," Bryant said. "It's an uphill battle. It's a long hill, at that. But he'll have us and he'll have me every step of the way."