Question regarding setting up HTTPS with Tailscale

Hi, I’ve installed Umbrel. Setup Nextcloud & Tailscale on the install. Later enabled MagicDNS and switched on HTTPS on Tailscale admin console.

Later ran tailscale cert <domain> inside the Tailscale docker instance, it succeeded. But when I try to visit the https domain I get an err saying ERR_CONNECTION_RESET . I ran the same command from the instance where I installed umbrel (on the host machine, not the docker) and that also seems to not make a difference. I don’t think I fully understand as of yet how certs are managed by Tailscale.

What am I missing?

I’m attempting the same thing but can’t even figure out how to run ‘tailscale cert’ to assign a certificate.

How did you manage it?

Update just for reference, I managed to obtain the certificate by running the following command whilst ssh’ed into Umbrel:

sudo docker exec -it tailscale_web_1 tailscale cert [tailscale machine name].[tailnet domain alias]

Where tailscale machine name and tailnet domain alias were assigned in the machines and DNS settings.

I found the name of the docker container using sudo docker ps which listed a container name for both web and Tor and ran the command in the non-Tor container.

This appeared to run successfully and create the necessary files on the server, but as with OP when I attempted to visit the domain whilst connected to Tailscale I also received the message:


Any Tailscale/DNS/TLS/HTTPS experts amongst us?

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In the Tailscale admin console, under Services, a list is presented of all running services. In mine, port 443 is not listed. I think the solution is to open port 443 in the Nginx config. However, the nginx.conf file will be overwritten when the software is updated, so this is not a good solution.