On the road I find WireGuard to be quirky when connecting to DNS names. When I'm on an IPv6 only network (like T-Mobile), connecting to a DNS name that offers A and AAAA, WireGuard on iOS prefers the A record, making me connect over one of T-Mobile's 464XLAT proxies which time out after x minutes. This then makes the connection look dead until I do something on my phone that re-enables it.

Tailscale doesn't have this issue.