I have not yet reproduced this on my Ubuntu 21.10 for lack of time, but
I ran into it on a Debian 11 machine I was converting to Netplan and
preparing to port the ifupdown scripts.

I tried ignoring unimportant interfaces, but no dice. So I ran an strace
on /lib/systemd/systemd-networkd-wait-online (attached). I failed to
understand what is really going on, but the program configures a epoll
instance. After some successful use of that something fails to happen
and the two minute timeout strikes. During that timeout, the program is
repeatedly looking at /run/systemd/netif/links/1, but it does not
change.

The machine has four interfaces: lo, ens3, dummy1 and tun0.
/run/systemd/netif/links/2 and /run/systemd/netif/links/3 are ens3 and
dummy1, 4 is probably tun0, being the last created, and the state is
ADDRESS_STATE=routable.

But /run/systemd/netif/links/1 is strange. This should be lo, but lo is 
configured:
1: lo: <LOOPBACK,UP,LOWER_UP> mtu 65536 qdisc noqueue state UNKNOWN group 
default qlen 1000
    link/loopback 00:00:00:00:00:00 brd 00:00:00:00:00:00
    inet 127.0.0.1/8 scope host lo
       valid_lft forever preferred_lft forever
    inet6 ::1/128 scope host 
       valid_lft forever preferred_lft forever

but /run/systemd/netif/links/1 is
ADMIN_STATE=unmanaged
OPER_STATE=carrier
CARRIER_STATE=carrier
ADDRESS_STATE=off

So I thought that adding a netplan configuration for lo might help.
Well, it doesn't. The strace is the same, except for the contents of the
netif file.

Please reopen this ticket and push it upstream. There is something
uncouth about systemd-networkd-wait-online's relationship with lo.

** Attachment added: "wait-online.strace"
   
https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1779340/+attachment/5577039/+files/wait-online.strace

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https://bugs.launchpad.net/bugs/1779340

Title:
  systemd-networkd-wait-online.service Failed to start Wait for Network
  to be Configured with bridge

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