Tailscale ssh to a gitpod container: "Unable to change owner or mode of tty stdin: Operation not permitted"

Bug description

I cannot tailscale ssh into a gitpod container. I've tried several different client devices with the same result.

Authentication via tailscale ssh works, but then the tty cannot be allocated and the process fails with:

Unable to change owner or mode of tty stdin: Operation not permitted

I can tailscale ssh into other non-gitpod containers without issue.

Steps to reproduce

In a gitpod container:

1. I've configured the TAILSCALE_AUTHKEY env var in gitpod with an ephemeral authkey
2. Open the gitpod https://github.com/gitpod-io/template-tailscale
3. Run tailscale up with your authkey and the ssh flag

On another device connected to the tailnet

• ssh -v gitpod@<tailnet ip for the gitpod container>

Workspace affected

all

Expected behavior

I expect to be able to SSH to the gitpod instance via tailscale

Example repository

https://github.com/gitpod-io/template-tailscale

Anything else?

I first reported this issue over at tailscale, but based on the findings of this gitpod issue it seems that this phenomenon may be a consequence of gitpod's ssh daemon + container setup.

Start with the gitpod-io/template-tailscale example repository and reproduce the Tailscale SSH connection in a Gitpod container. Review the linked Tailscale issue and Gitpod issue 3424 for findings about the SSH daemon and container setup. Done means a Tailscale SSH session can allocate its tty without the ownership or mode error.