I've done a bit more work on this to see if I can get everything in.

If I do a manual configuration, switch off roaming mode and enter the
SSID details by hand then I can get an association and the network
works.


Process to reproduce:

Restart access point.
Restart laptop in roaming mode.
Login. 
Fire up a terminal running 'iwevent' and 'tail -f /var/log/daemon.log'
Enter incorrect WPA password. 
 - Network manager will now try and associate with access point, and eventually 
ask for a new key (usually in a minimised window which is annoying).
Enter correct WPA password.
- Network manager will log an assertion failure 
'nm_utils_supplicant_request_with_check: assertion 'ctrl !=NULL' failed. This 
comes after a 'Error opening supplicant global control interface' earlier on. 
- Association fails.
- (You get the same association failure without the assertion fault if you 
enter the correct WPA password first time).
Select manual configuration and enter 'network admin' password.
Switch off roaming mode on the wireless and select the ESSID from the drop down 
list.
Enter the correct WPA password and select DHCP configuration.
- Access point will associate correctly.
Go back into the wireless configuration and switch 'roaming mode' back on.
- Once network manager wakes up, it will associate correctly with the AP (and 
probably ask for the WPA password again - probably with a window in the 
background or minimised).
If you now reboot the machine, then network manager appears to work correctly 
(although it doesn't retrieve the WPA password from the keyring - you have to 
enter it again). Multiple reboots appear to have the same effect until the AP 
is restarted

-- 
[Gutsy]Network Manager Applet can't connect wireless with ipw3945 driver
https://bugs.launchpad.net/bugs/121439
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Bugs, which is the bug contact for Ubuntu.

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