I have to dissent.  This is not a Ubuntu bug but a networkmanager bug.
I have experienced this behavior with my dell inspiron 1520 which uses
an IPW3945 chipset in two different distros.  Arch and Debian Sid.  The
problem is in networkmanager.  a workaround is to try to use the command
line + sudo to run

iwconfig ethN essid whatever ap whatever channel whatever

repeatedly while it's trying to associate.  it for some reason
unassociates when trying get the key and configure WPA2, and gets
confused.  this workaround is how I connected this very morn.

here's some extra info if it helps any. my WPA2 network is configured
with a hidden ESSID.  there are two other networks in the area, one runs
WPA2 one runs WEP.  both show essids. my network works fine if I
configure it manually using wpa supplicant and iwconfig.  it worked fine
in arch without using network manager.  it works fine in *shudders*
vista.  (don't look at me like that, I play a game with my wife, and xp
doesn't install on my laptop)

I can provide more detailed information on request, but this is just to
confirm that it's not ubuntu specific.

-- 
WPA2 Personal wireless networks don't work without manual configuration
https://bugs.launchpad.net/bugs/106129
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