Debian systemd network-online.target not working?

Since you're using /etc/network/interfaces, you'll need a systemd service to monitor the status of each interface. Check to see if you have /lib/systemd/system/ifup-wait-all-auto.service (installed by the ifupdown package in Ubuntu 15.04). If not, then create /etc/systemd/system/ifup-wait-all-auto.service, and paste in the following:

[Unit]
Description=Wait for all "auto" /etc/network/interfaces to be up for network-online.target
Documentation=man:interfaces(5) man:ifup(8)
DefaultDependencies=no
After=local-fs.target
Before=network-online.target

[Service]
Type=oneshot
RemainAfterExit=yes
TimeoutStartSec=2min
ExecStart=/bin/sh -ec '\
  for i in $(ifquery --list --exclude lo --allow auto); do INTERFACES="$INTERFACES$i "; done; \
  [ -n "$INTERFACES" ] || exit 0; \
  while ! ifquery --state $INTERFACES >/dev/null; do sleep 1; done; \
  for i in $INTERFACES; do while [ -e /run/network/ifup-$i.pid ]; do sleep 0.2; done; done'

[Install]
WantedBy=network-online.target

This is the service file as present on an Ubuntu 15.04 system, but with the [Install] section added in to make things a little easier. I'm hoping that the behavior of ifup in Ubuntu 15.04 is the same as the behavior of ifup in Debian Jessie. If not, some modification will be necessary (particularly with the last line).

Then, run sudo systemctl enable ifup-wait-all-auto.service. After rebooting your computer, you should see that the network-online.target is reached after the interfaces are brought up (at least).

I once found an answer on Github that solved it by continuously trying to ping a server. Only when the ping comes through, the service continues:

[Service]
ExecStartPre=/bin/sh -c 'until ping -c1 google.com; do sleep 1; done;'
ExecStart=<your command>

I replaced google.com with my own server because my main script needed to connect to my server.