Hello, I had a very similar issue in Debian 9.
A Debian 9 system that indeed has interface configured with allow-hotplug stanza in /etc/network/interfaces file, it fails to mount nfs shares (over nfs4.0). From the journal it seems that dhclient finishes **after** networking.service is activated. Networking.service is the one that calls ifup -a. Hence other services including nfs mounts are started early. But if auto ensxx is added to interfaces then ordering is correct (networking service is activated after ifup -a). I don't know if this is documented somewhere. But it is important to note! VG Debian 9.13 ifupdown 0.8.19 systemd 232-25+deb9u13 /etc/fstab 10.2.0.10:/data/oc-data /data/oc-data nfs timeo=20,_netdev 0 0 /etc/network/intefaces # The primary network interface allow-hotplug ens14 iface ens14 inet dhcp Logs excerpt from "journalctl -b" after a failed auto mount reboot allow-hotplug ens14 iface ens14 inet dhcp Μάρ 02 15:37:08 host1 systemd[1]: Started Raise network interfaces. Μάρ 02 15:37:10 host1 systemd[1]: Reached target Remote File Systems (Pre). Μάρ 02 15:37:10 host1 systemd[1]: Reached target RPC Port Mapper. Μάρ 02 15:37:10 host1 systemd[1]: Reached target Network is Online. Μάρ 02 15:37:10 host1 dhclient[439]: Copyright 2004-2016 Internet Systems Consortium Μάρ 02 15:37:10 host1 systemd[1]: Mounting /data/oc-data... Μάρ 02 15:37:11 host1 dhclient[439]: DHCPDISCOVER on ens14 to 255.255.255.255 port 67 interval 7 Μάρ 02 15:37:11 host1 dhclient[439]: DHCPREQUEST of 10.2.0.4 on ens14 to 255.255.255.255 port 67 Μάρ 02 15:37:11 host1 dhclient[439]: DHCPOFFER of 10.2.0.4 from 10.2.0.1 Μάρ 02 15:37:11 host1 dhclient[439]: DHCPACK of 10.2.0.4 from 10.2.0.1 Μάρ 02 15:37:11 host1 systemd[1]: data-oc\x2ddata.mount: Mount process exited, code=exited status=32 Μάρ 02 15:37:11 host1 systemd[1]: Failed to mount /data/oc-data. ------- #allow-hotplug ens14 auto ens14 iface ens14 inet dhcp Μάρ 02 16:17:52 host1 systemd[1]: Starting Raise network interfaces.. Μάρ 02 16:17:56 host1 dhclient[455]: DHCPOFFER of 10.2.0.4 from 10.2.0.1 Μάρ 02 16:17:56 host1 ifup[420]: DHCPOFFER of 10.2.0.4 from 10.2.0.1 Μάρ 02 16:17:56 host1 dhclient[455]: DHCPACK of 10.2.0.4 from 10.2.0.1 Μάρ 02 16:17:56 host1 ifup[420]: DHCPACK of 10.2.0.4 from 10.2.0.1 Μάρ 02 16:17:57 host1 ifup[420]: bound to 10.2.0.4 -- renewal in 2959 seconds. Μάρ 02 16:17:57 host1 systemd[1]: Started Raise network interfaces. Μάρ 02 16:17:57 host1 systemd[1]: Reached target Network. Μάρ 02 16:17:57 host1 systemd[1]: Reached target Network is Online. Μάρ 02 16:17:57 host1 systemd[1]: Mounting /data/oc-data... Μάρ 02 16:17:59 host1 systemd[1]: Mounted /data/oc-data. ---- allow-hotplug ens14 auto ens14 iface ens14 inet dhcp Μάρ 02 16:28:23 host1 systemd[1]: Starting Raise network interfaces... Μάρ 02 16:28:25 host1 sh[375]: DHCPOFFER of 10.2.0.33 from 10.2.0.1 Μάρ 02 16:28:25 host1 dhclient[422]: DHCPOFFER of 10.2.0.33 from 10.2.0.1 Μάρ 02 16:28:25 host1 dhclient[422]: DHCPACK of 10.2.0.33 from 10.2.0.1 Μάρ 02 16:28:25 host1 sh[375]: DHCPACK of 10.2.0.33 from 10.2.0.1 Μάρ 02 16:28:26 host1 dhclient[422]: bound to 10.2.0.33 -- renewal in 2976 seconds. Μάρ 02 16:28:26 host1 systemd[1]: Started Raise network interfaces. Μάρ 02 16:28:26 host1 systemd[1]: Reached target Network. Μάρ 02 16:28:26 host1 systemd[1]: Reached target Network is Online. Μάρ 02 16:28:26 host1 systemd[1]: Mounting /data/oc-data...