I have the same problem too: wpasupplicant doesn't start automatically
at boot and to get a working interface I have to:

$ ifdown eth1  [<--]
$ ifup eth1

So it seems that the network is actually started and configured, only
wpasupplicant refuses to start.

I have only one suspect: maybe there is some odd interaction with udev rule 
ifupdown.rules? Udev is started before than Networking in the init process and 
(as far as I understood) tries to configure the interfaces it found. So, when 
Networking starts, interfaces are already brought up (and in fact I can't do 
ifup directly to make eth1 working).
Am I saying nonsense?

-- 
wpasupplicant doesn't start when the network start
https://bugs.launchpad.net/bugs/44194
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