`update` hangs via ssh

I've been unable to upgrade Xcode on any of my Jenkins slave nodes via ssh. I have tried both tmux into multiple machines and ssh-ing into only one to run the command. Both have failed (or rather, just stall) with and without reattach-to-user-namespace being used.

$ mas list
409183694 Keynote (7.2)
497799835 Xcode (9.0)
409201541 Pages (6.2)
409203825 Numbers (4.2)

$ mas outdated
409203825 Numbers (4.2 -> 4.3.1)
409183694 Keynote (7.2 -> 7.3.1)
409201541 Pages (6.2 -> 6.3.1)
497799835 Xcode (9.0 -> 9.2)

$ sudo mas upgrade 497799835 
Password:
Warning: Nothing found to upgrade

$ mas upgrade 497799835 
Upgrading 1 outdated application:
Xcode (9.2)

/// No progress after a few hours.

$ reattach-to-user-namespace mas upgrade 497799835 
Upgrading 1 outdated application:
Xcode (9.2)

/// No progress after a few hours.

It hangs and never completes. I've left it running for hours without success.

Note: If I screen share into the mac mini and run it via terminal, it works just fine, however, that approach won't scale and isn't feasible for the number of macs nodes we are using with Jenkins.

I've removed all other installations of Xcode on the system and have also removed the "Install OSX High Sierra.app" in hopes that it would change any behavior when via ssh. Again, regardless of the two above environment characteristics (Xcode.app + Xcode8.3.app + Install OSX High Sierra.app), running mas upgrade still works via screenshare.

Can you please advise? Is there a way to enable verbose output to provide any additional details necessary?

Possibly related, using mas via a Brewfile hangs indefinitely as well for me.

brew 'mas'
mas 'Xcode', id: 497799835

No source files or tests are named. Start by reproducing mas upgrade 497799835 over SSH and through screen sharing, comparing the behavior with and without reattach-to-user-namespace; also check the reported Homebrew Brewfile invocation. Done means the upgrade completes non-interactively over SSH and through the Brewfile path.