Yup, obviously my workaround isn't much help when you have two
interfaces. I suggest locally editing the ifup.d script, I don't think
restarting is an appropriate response for everyone.

Even better, work on improving cntlm :)

Sorry, I can't understand what your issue with "config 2" is. Was the
parent proxy available at the time that cntlm started? It needs to be.

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https://bugs.launchpad.net/bugs/825593

Title:
  cntlm does not work at reboot

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