I have tried a Gutsy Tribe 5 desktop CD and the problem still exists.
Only now nm-applet does not pop up the dialogue for a new key, it just
disables the interface. During it's attempts to connect I can
successfully ping my other Ubuntu PC via it's IPv6 address. So I know
that the connection along with it's WPA encryption works.

>From the syslog (see attached), I can see that after dhcp fails the
interface is disabled, even though avahi-autoip has been enabled. What's
the point of avahi-autoip if it's not going to be allowed to work?

Two more tries and it gets an address from the DHCP server and the
interface is up and working. So this is only a problem when DHCP fails.

** Attachment added: "syslog of DHCP failure"
   http://launchpadlibrarian.net/9117478/syslog.txt.gz

-- 
network manager disables wireless if dhcp times out
https://bugs.launchpad.net/bugs/84103
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