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When you put your server's tailscale IP in the dns, anything that looks up that dns gets the tailscale IP. You only need to connect the devices you want to have connect to the server to the same tailscale network, and your system will handle the routing.
Okay, that makes sense. Would that help to set up NextCloud or other services that require https?
It doesn't really help with connecting my calendar to an external scheduling app that is not based on my device.