Hmm apparently After=network-online.target may not be enough as I'm still running into a race.

bdmurray@clean-xenial-amd64:~$ systemctl status whoopsie
● whoopsie.service - crash report submission daemon
   Loaded: loaded (/lib/systemd/system/whoopsie.service; enabled; vendor preset: enabled)
   Active: active (running) since Fri 2017-07-21 11:51:09 PDT; 8s ago
 Main PID: 587 (whoopsie)
   CGroup: /system.slice/whoopsie.service
           └─587 /usr/bin/whoopsie -f

Jul 21 11:51:09 clean-xenial-amd64 systemd[1]: Started crash report submission daemon.
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] Using lock path: /var/lock/whoopsie/lock
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] offline
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] Cannot reach: https://daisy.ubuntu.com
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] The default IPv4 route is: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] Not a paid data plan: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] Found usable connection: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:51:10 clean-xenial-amd64 whoopsie[587]: [11:51:10] online
bdmurray@clean-xenial-amd64:~$ sudo shutdown -r now
[sudo] password for bdmurray:
Connection to clean-xenial-amd64.local closed by remote host.
Connection to clean-xenial-amd64.local closed.

Last login: Fri Jul 21 11:51:11 2017 from 192.168.122.1
bdmurray@clean-xenial-amd64:~$ systemctl status whoopsie
● whoopsie.service - crash report submission daemon
   Loaded: loaded (/lib/systemd/system/whoopsie.service; enabled; vendor preset: enabled)
   Active: active (running) since Fri 2017-07-21 11:52:46 PDT; 4min 6s ago
 Main PID: 596 (whoopsie)
   CGroup: /system.slice/whoopsie.service
           └─596 /usr/bin/whoopsie -f

Jul 21 11:52:46 clean-xenial-amd64 systemd[1]: Started crash report submission daemon.
Jul 21 11:52:46 clean-xenial-amd64 whoopsie[596]: [11:52:46] Using lock path: /var/lock/whoopsie/lock
Jul 21 11:52:46 clean-xenial-amd64 whoopsie[596]: [11:52:46] Could not get the Network Manager state:
Jul 21 11:52:46 clean-xenial-amd64 whoopsie[596]: [11:52:46] GDBus.Error:org.freedesktop.DBus.Error.ServiceUnknown: The name org.freedesktop.NetworkManager was
Jul 21 11:52:46 clean-xenial-amd64 whoopsie[596]: [11:52:46] offline
Jul 21 11:52:46 clean-xenial-amd64 whoopsie[596]: [11:52:46] Cannot reach: https://daisy.ubuntu.com
Jul 21 11:52:47 clean-xenial-amd64 whoopsie[596]: [11:52:47] The default IPv4 route is: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:52:47 clean-xenial-amd64 whoopsie[596]: [11:52:47] Not a paid data plan: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:52:47 clean-xenial-amd64 whoopsie[596]: [11:52:47] Found usable connection: /org/freedesktop/NetworkManager/ActiveConnection/0
Jul 21 11:52:47 clean-xenial-amd64 whoopsie[596]: [11:52:47] online

Regardless, this isn't making the situation worse and fixes it some of the time so I think it is still worth letting into -updates while we further sort out the matter.