I have this problem too, still not resolved.

I'm on Gutsy with all updates, using WPA through the network-manager
with a static IP. I have no error message in dmesg about WPA but the
network isn't active at reboot, I have to do a /etc/init.d/networking
restart to make it works.

My /etc/network/interfaces look like this :

auto eth3
iface eth3 inet static
address 192.168.1.100
netmask 255.255.255.0
gateway 192.168.1.1
wpa-psk ac22b218cf97263ef58887a86f9e32605bd638017a9c4dacd8d80e8f6bd07696
wpa-driver wext
wpa-key-mgmt WPA-PSK
wpa-proto WPA
wpa-ssid strangebanality

When doing a /etc/init.d/networking restart, I get this in dmesg but
nothing more :

[  231.332000] ADDRCONF(NETDEV_UP): eth3: link is not ready
[  231.392000] ADDRCONF(NETDEV_CHANGE): eth3: link becomes ready
[  232.480000] ieee80211_crypt: registered algorithm 'TKIP'

Is it really a boot order problem?

-- 
Boot order problem
https://bugs.launchpad.net/bugs/53387
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