Found these other bugs which look related:

https://bugs.launchpad.net/ubuntu/+source/openvpn/+bug/1598522

https://bugs.launchpad.net/ubuntu/+source/openvpn/+bug/1580356 (marked
as dup of the above)

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https://bugs.launchpad.net/bugs/1689833

Title:
  OpenVPN server does not start properly on boot

Status in openvpn package in Ubuntu:
  Triaged
Status in systemd package in Ubuntu:
  New

Bug description:
  OpenVPN intermittently fails to bind to local address during boot on
  Ubuntu Server 16.04.2 LTS. Sometimes it succeeds, sometimes it does
  not.

  /var/log/openvpn.log
  Wed May 10 15:42:02 2017 OpenVPN 2.3.10 x86_64-pc-linux-gnu [SSL (OpenSSL)] 
[LZO] [EPOLL] [PKCS11] [MH] [IPv6] built on Feb  2 2016
  Wed May 10 15:42:02 2017 library versions: OpenSSL 1.0.2g  1 Mar 2016, LZO 
2.08
  Wed May 10 15:42:02 2017 Diffie-Hellman initialized with 2048 bit key
  Wed May 10 15:42:02 2017 Control Channel Authentication: using 
'./easy-rsa/keys/ta.key' as a OpenVPN static key file
  Wed May 10 15:42:02 2017 Outgoing Control Channel Authentication: Using 160 
bit message hash 'SHA1' for HMAC authentication
  Wed May 10 15:42:02 2017 Incoming Control Channel Authentication: Using 160 
bit message hash 'SHA1' for HMAC authentication
  Wed May 10 15:42:02 2017 Socket Buffers: R=[212992->212992] S=[212992->212992]
  Wed May 10 15:42:02 2017 TCP/UDP: Socket bind failed on local address 
[AF_INET]192.168.4.254:1194: Cannot assign requested address
  Wed May 10 15:42:02 2017 Exiting due to fatal error

  In case it does not start, running 'sudo service openvpn start' fixes
  that problem.

  /var/log/openvpn.log
  Wed May 10 15:42:43 2017 OpenVPN 2.3.10 x86_64-pc-linux-gnu [SSL (OpenSSL)] 
[LZO] [EPOLL] [PKCS11] [MH] [IPv6] built on Feb  2 2016
  Wed May 10 15:42:43 2017 library versions: OpenSSL 1.0.2g  1 Mar 2016, LZO 
2.08
  Wed May 10 15:42:43 2017 Diffie-Hellman initialized with 2048 bit key
  Wed May 10 15:42:43 2017 Control Channel Authentication: using 
'./easy-rsa/keys/ta.key' as a OpenVPN static key file
  Wed May 10 15:42:43 2017 Outgoing Control Channel Authentication: Using 160 
bit message hash 'SHA1' for HMAC authentication
  Wed May 10 15:42:43 2017 Incoming Control Channel Authentication: Using 160 
bit message hash 'SHA1' for HMAC authentication
  Wed May 10 15:42:43 2017 Socket Buffers: R=[212992->212992] S=[212992->212992]
  Wed May 10 15:42:43 2017 ROUTE_GATEWAY 192.168.4.1/255.255.255.0 IFACE=ens4 
HWADDR=52:54:00:f0:26:0c
  Wed May 10 15:42:43 2017 TUN/TAP device tun0 opened
  Wed May 10 15:42:43 2017 TUN/TAP TX queue length set to 100
  Wed May 10 15:42:43 2017 do_ifconfig, tt->ipv6=0, 
tt->did_ifconfig_ipv6_setup=0
  Wed May 10 15:42:43 2017 /sbin/ip link set dev tun0 up mtu 1500
  Wed May 10 15:42:43 2017 /sbin/ip addr add dev tun0 local 172.16.1.1 peer 
172.16.1.2
  Wed May 10 15:42:43 2017 /sbin/ip route add 172.16.1.0/24 via 172.16.1.2
  Wed May 10 15:42:43 2017 GID set to nogroup
  Wed May 10 15:42:43 2017 UID set to nobody
  Wed May 10 15:42:43 2017 UDPv4 link local (bound): [AF_INET]192.168.4.254:1194
  Wed May 10 15:42:43 2017 UDPv4 link remote: [undef]
  Wed May 10 15:42:43 2017 MULTI: multi_init called, r=256 v=256
  Wed May 10 15:42:43 2017 IFCONFIG POOL: base=172.16.1.4 size=62, ipv6=0
  Wed May 10 15:42:43 2017 IFCONFIG POOL LIST
  Wed May 10 15:42:43 2017 Initialization Sequence Completed

  My guess is that systemd starts OpenVPN too early before the network
  is brought up sufficiently. Running 'sudo systemctl edit --full
  openvpn' and adding 'Wants=network-online.target' does not change that
  behaviour.

  user@server:~$ sudo systemd-analyze critical-chain
  graphical.target @2.160s
  └─multi-user.target @2.159s
    └─ntp.service @2.054s +104ms
      └─remote-fs.target @2.052s
        └─remote-fs-pre.target @2.052s
          └─open-iscsi.service @1.993s +57ms
            └─iscsid.service @1.942s +47ms
              └─network-online.target @1.941s
                └─network.target @1.929s
                  └─networking.service @1.793s +134ms
                    └─apparmor.service @1.140s +395ms
                      └─local-fs.target @1.140s
                        └─local-fs-pre.target @1.139s
                          └─lvm2-monitor.service @602ms +536ms
                            └─lvm2-lvmetad.service @773ms
                              └─systemd-journald.socket @574ms
                                └─-.slice @500ms

  The boot time is quite short. Clean install with the additional
  packages ntp and openssh-server. This happens both on bare metal and
  as a Virtual Machine (KVM) as well.

  /etc/openvpn/server.conf
  local 192.168.4.254
  port 1194
  proto udp
  dev tun
  ca ./easy-rsa/keys/ca.crt
  cert ./easy-rsa/keys/crt.crt
  key ./easy-rsa/keys/key.key
  dh ./easy-rsa/keys/dh2048.pem
  tls-auth ./easy-rsa/keys/ta.key 0
  server 172.16.1.0 255.255.255.0
  ifconfig-pool-persist ipp.txt
  push "route 192.168.0.0 255.255.255.0"
  push "route 192.168.4.0 255.255.255.0"
  keepalive 10 120
  comp-lzo
  max-clients 5
  user nobody
  group nogroup
  persist-key
  persist-tun
  status openvpn-status.log
  log-append  /var/log/openvpn.log
  verb 3

  /etc/network/interfaces
  # The loopback network interface
  auto lo
  iface lo inet loopback

  # The primary network interface
  auto ens3
  iface ens3 inet static
    address 192.168.0.1
    netmask 255.255.255.0
    network 192.168.0.0
    broadcast 192.168.0.255

  # The secondary network interface
  auto ens4
  iface ens4 inet static
    address 192.168.4.254
    netmask 255.255.255.0
    network 192.168.4.0
    broadcast 192.168.4.255
    gateway 192.168.4.1

  user@server:~$ sudo apt-cache policy openvpn
  openvpn:
    Installed: 2.3.10-1ubuntu2
    Candidate: 2.3.10-1ubuntu2
    Version table:
   *** 2.3.10-1ubuntu2 500
          500 http://de.archive.ubuntu.com/ubuntu xenial/main amd64 Packages
          100 /var/lib/dpkg/status

  user@server:~$ sudo apt-cache policy systemd
  systemd:
    Installed: 229-4ubuntu17
    Candidate: 229-4ubuntu17
    Version table:
   *** 229-4ubuntu17 500
          500 http://de.archive.ubuntu.com/ubuntu xenial-updates/main amd64 
Packages
          100 /var/lib/dpkg/status
       229-4ubuntu10 500
          500 http://security.ubuntu.com/ubuntu xenial-security/main amd64 
Packages
       229-4ubuntu4 500
          500 http://de.archive.ubuntu.com/ubuntu xenial/main amd64 Packages

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