I also have this issue on a Macbook Pro 5,5 running Ubuntu 10.04. NM
will try to connect for 5 minutes (with the laptop sitting right next to
the wireless router), and will either re-prompt me for the WPA2 password
a dozen times, or just give up and say it was disconnected (even though
it was never connected in the first place). Only about 1 in 12 times it
will connect successfully. This essentially makes wireless networking
unusuable for me using NM. I've had no issues at all connecting to the
same wireless router with other machines (Ubuntu desktop using a USB
wireless dongle, and an Android phone), so the issue doesn't seem to be
on the router's side.

The only workaround I've found is to remove ALL network-manager
packages, and install the equivalent Wicd packages, which is able to
connect immediately. It would be nice to have similar functionality with
NM, since it has a more intuitive interface than Wicd IMHO.

-- 
network manager takes long time to connect then connection drops - ath9k
https://bugs.launchpad.net/bugs/395919
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