I have an Atom and Chrome AppImages connected, so this looks specific to the Hyper plugin. I'm on Kubuntu 20.04, so can't try iterm2. I tried both 3.1.3 and 3.1.4 AppImages of Hyper, both same result. Maybe there is a way to access updating via the CLI?
One unrelated comment is that it is unclear how to start using Serenadeai even for dictation without any plugins installed. It appears to block progress until VSCode or Atom is installed.