Hey @moses, I’ve run into this issue before when I’ve had DNS issues on my machine. In that scenario, the machine on which I was running waypoint install did not have DNS properly configured for lookups on hostnames in the .consul domain. I’m not sure if that’s the case here, but it appears that for some reason or another, your machine couldn’t connect to the server at the address waypoint-ui.service.us-west1.consul.
You could also attempt to run waypoint server bootstrap to bootstrap your new server and set the server address to an address which your machine can access, so long as it routes to the Waypoint server. This can be done with the -server-addr flag.