Package: ifupdown2 Version: 1.0~git20170114-1~bpo8+1 ifupdown2 requires python-pkg-resources but doesn't list it as dependency. When rebooting a system with ifupdown2 the network would not come up without that package since the python script requires the `pkg_resourcess` module.
The debian system was fully patched at the point of restart. An package upgrade was performed just before the reboot. Backports kernels (linux 4.9 at this time) are installed. I suggest to add `python-pkg-resources` to the dependencies of ifupdown2. This bug probably also affects the upcoming strech release but I didn't test it there. Regards, Andi