I have the same problem when using gutsy in persistent mode from a usb
stick.  I know persistence has been broken, but I have been thinking
this failure of gnome network manager to maintain the key might be a
different issue because some of the persistent functionality in gutsy
has actually worked for me.

Note, I believe some people may have experienced this same network
manager issue in the patched feisty iso that was prepared in which
persistence worked.  Don't know if that was the same problem as this one
(particularly if normal (non live-cd) feisty installations didn't
experience this problem.  But, I wanted to mention that in case it is
possible this issue was introduced by changes back in feisty (don't know
if that might help in the trouble shooting).

Alexander, it might be intersting to see if your problem persists with
the feisty version of gnome network manager and, if it does, with the
edgy version of network manager.  You could revert to each of these by
creating a preferences file in your /etc/apt directory and pinning gnome
network manager at the feisty and edgy versions of the gnome network
manager, respectively.  (Don't know if they will be compatible, but you
might try if you have time.  I might try that as well).

-- 
WPA - network-manager keeps asking for password
https://bugs.launchpad.net/bugs/131233
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