"failed to connect to local tailscaled" on self-hosted runners

Running my workflow on github's hosted runner works fine, but when I switch to self-hosted runners (using a DinD approach and ultimately running in a nimmis/ubuntu:latest container) I'm finding that the action fails (see GitHub workflow output):

  sudo -E tailscaled --state=mem: ${ADDITIONAL_DAEMON_ARGS} 2>~/tailscaled.log &
  # And check that tailscaled came up. The CLI will block for a bit waiting
  # for it. And --json will make it exit with status 0 even if we're logged
  # out (as we will be). Without --json it returns an error if we're not up.
  sudo -E tailscale status --json >/dev/null
  shell: bash --noprofile --norc -e -o pipefail {0}
  env:
    ADDITIONAL_DAEMON_ARGS: 
  
failed to connect to local tailscaled; it doesn't appear to be running (sudo systemctl start tailscaled ?)
Error: Process completed with exit code 1.

I think the issue may have something to do with the CLI not blocking as expected, since as you can see in the image below with the timestamps, the entire thing is completed in seconds.

The only change I made to the nimmis/ubuntu:latest image was to run:

apt-get update
apt-get install -y sudo --fix-missing

since sudo was not installed by default since the only user is root.

Maybe some other error is being thrown by sudo -E tailscale status --json but it's being swallowed by the >/dev/null ?

EDIT: No, it's not redirecting stderr, only stdout... 🤔

No repository files or tests are named. Start by reproducing the workflow on a self-hosted runner using the nimmis/ubuntu:latest DinD setup, then inspect tailscaled.log and the output of the shown commands. Done means the action connects successfully without the local tailscaled error.