I did some more troubleshooting.  I can get the exact same results by
manually editing the /etc/networking/interfaces and restarting
networking thus yes -- I mis-categorized this bug report by selecting
"gnome-system-tools" package.  I don't know if the problem is in the
ifupdown package, or wireless-tools (iwconfig), or elsewhere?

What appears to be happening is that any values the card uses during startup 
are retained until they are explicitly changed using iwconfig.   For instance, 
my config file (/etc/network/interfaces) has:
auto eth1
iface eth1 inet dhcp
wireless-essid WORKACCESSPOINT
wireless-key s:WORKWEPKEY
but since I am at home these values are invalid.  So I boot (and get no 
connectivity) and then edit the config file to change the essid line to 
"wireless-essid HOMEACCESSPOINT" and remove the entry for "key".  Even if I do 
"$ sudo /etc/init.d/networking restart" it appears that it still is trying to 
do WEP authentication.  Unless I explicitly issue an "$ sudo iwconfig eth1 key 
off" first, the ifup appears to still attempt to use the WEP key that was in 
the config file during boot -- even though the wireless-key line has been 
removed.

So the problem appears to be that "$ sudo /etc/init.d/networking
restart" isn't starting the network similar to how it starts from a
power-off condition and instead it only changes the values that are
explicitly listed in the /etc/network/interfaces.

Here's another example.
With an invalid essid in the config file at boot, if I then do an "$ iwconfig 
eth1", it will list frequency 2.437 GHz which is Channel 06 -- the first access 
point found when I "$ iwlist eth1 scanning" is channel 6 so I am suspecting 
that this is why it show this specific frequency.  After I change the config 
file to "wireless-essid HOMEACCESSPOINT" and then restart networking, the 
dhclient part of the restart will still report NO DHCPOFFERS".  I then do "$ 
iwconfig eth1" which now shows the correct ESSID but it still shows the 2.437 
GHz frequency, and it also still shows "Access Point: Invalid".  If I make no 
further changes to the config file and then reboot, I'll get a connection no 
problem.  But to get the changes to the config file to take effect without 
rebooting I need to manually do:
  $ sudo iwconfig eth1 channel 11 essid "HOMEACCESSPOINT"
  $ sudo /etc/init.d/networking restart 
and it then restarts and connects no problem.

To answer your question about whether or not dhcp server is at fault, I
get the same problem at work (Airport Extreme AP) as at home (Linksys
BEFWS114 router), so I don't think dhcp server is at fault -- especially
since every dhclient subsequent to an iwconfig (with channel, essid, and
key)  is always successful.

Is what I am experiencing (changes to config not taking effect until
iwconfig or reboot) unique?

-- 
Changing ESSID requires reboot or, or manual iwconfig for changes to take effect
https://launchpad.net/bugs/80499

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