Public bug reported:

recently i have upgraded 4 VM-based systems to 16.04.1 LTS (Xenial
Xerus). on startup, settings within /etc/network/interfaces do not
appear to be taking effect reliably. specifically, the gateway and dns-
settings have been problematic for me. on subsequent restarts, all or
some of the settings take effect other times the gateway is set and the
dns- options are not set. very problematic when the default gateway is
not added to the routing table.

the dns- settings were a bit easier to illustrate the issue. i added a
comment to /etc/resolvconf/resolv.conf.d/base (# base) &
etc/resolvconf/resolv.conf.d/tail (# tail).

$ cat /etc/resolvconf/resolv.conf.d/*
# base
# Dynamic resolv.conf(5) file for glibc resolver(3) generated by resolvconf(8)
#     DO NOT EDIT THIS FILE BY HAND -- YOUR CHANGES WILL BE OVERWRITTEN
# tail

on startup on 1 of the systems showed this:
$ cat /etc/resolv.conf
# Dynamic resolv.conf(5) file for glibc resolver(3) generated by resolvconf(8)
#     DO NOT EDIT THIS FILE BY HAND -- YOUR CHANGES WILL BE OVERWRITTEN
# tail

you can see the "# base" comment wasn't added.
let me know if i can add anymore details or if this should be posted somewhere 
else.

$ lsb_release -rd
Description:    Ubuntu 16.04.1 LTS
Release:        16.04

$ apt-cache policy ifupdown
ifupdown:
  Installed: 0.8.10ubuntu1.1
  Candidate: 0.8.10ubuntu1.1
  Version table:
 *** 0.8.10ubuntu1.1 500
        500 http://us.archive.ubuntu.com/ubuntu xenial-updates/main amd64 
Packages
        100 /var/lib/dpkg/status
     0.8.10ubuntu1 500
        500 http://us.archive.ubuntu.com/ubuntu xenial/main amd64 Packages

$ apt-cache policy resolvconf
resolvconf:
  Installed: 1.78ubuntu2
  Candidate: 1.78ubuntu2
  Version table:
 *** 1.78ubuntu2 500
        500 http://us.archive.ubuntu.com/ubuntu xenial/main amd64 Packages
        500 http://us.archive.ubuntu.com/ubuntu xenial/main i386 Packages
        100 /var/lib/dpkg/status

** Affects: ifupdown (Ubuntu)
     Importance: Undecided
         Status: New

** Affects: resolvconf (Ubuntu)
     Importance: Undecided
         Status: New

** Also affects: resolvconf (Ubuntu)
   Importance: Undecided
       Status: New

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https://bugs.launchpad.net/bugs/1628552

Title:
  on startup gateway & dns- options in /etc/network/interfaces are not
  always set

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