The error occurs when using the linuxserver nextcloud image. This image configures its nginx reverse proxy to listen on 443, which you can then bind to a host port for the usual WebUI. Tailscale serve also tries to forward a targe portt to port 443, hence the clash. So you have two options: 1. configure tailscale (via the advanced setting Tailscale Serve Protocol Port) to forward the target port to a different port, e.g. 444, and append that port to your tailscale url. make nginx not listen on 443 and configure tailscale to forward port 80 to 443. This means that the regular WebUI will only be accessible via http, but you won't need to append a port to your tailscale url. To do this you need the following: set Tailscale Serve Port to 80 comment out or delete the two lines configuring nginx 443 listeners in /mnt/user/appdata/nextcloud/nginx/site-confs/default.conf Should look something like: ``` ... server { listen 80 default_server; listen [::]:80 default_server; # listen 443 ssl default_server; # listen [::]:443 ssl default_server; ... ``` run the nextcloud web installer add the other url to your trusted domains config, i.e. if you ran the installer via the tailscale url, add the regular WebUI IP:PORT to the trusted domains, otherwise add the tailscale url. You need to add a new entry to the trusted_domains settings in /mnt/user/appdata/nextcloud/www/nextcloud/config/config.php. The initial number is the index, so you need to increment that by one. Should look like: ``` 'trusted_domains' => array ( 0 => <unraid ip>:<the webui port you configured>, 1 => nextcloud.yourtailnet.ts.net, ), ```