IPad & 3502i WAP wlc 5508 H-REAP

Question

I have a wierd situation occouring at a new remote location.
Here is my scheme.
At my phyiscal location =WHQ
wlc 5508 (7.0.98.0)
vlan 800
ssid KWD-Guest
open authentication
wep 48bit key
(ACL restricted to internet only access)
Remote physical location = 80NY 
2821 router (12.4ios) - routes and dhcp for the locations networks.
3560-48 switch     - user connections and WAP connections.
3502i WAP - H-REAP back to WHQ for management and configuration.
Remote physical location = 1441NY
3825 router (12.4ios) - routes and dhcp for the locations networks.
3560-48 switch     - user connections and WAP connections.
1131AG WAP - H-REAP back to WHQ for management and configuration.
Here is the issue we are running into.
At 80NY the users want to connect to the guest vlan 800 ssid KWD-Guest with iPads and smart phones (model unknown).
They can see the ssid broadcasting. Try to connect to the ssid, input the wep key. wait, wait and time out on dhcp, giving themselves a 168.x.x.x addy
From the router side, I can see the dhcp request on the correct vlan hitting the correct dhcp pool.
The router hands out a valid ip address and associates it to the correct wireless devices Mac-Address
But as I said the client times out waiting for the dhcp address.
Now the kicker here is that the very same iPad and smart phone CAN connect to the guest ssid at 1441NY which is also hosted off the same 5508 at WHQ.
The only difference I see is the WAP model and the network addresses I hand out at each location.
To the best of my ability I have double checked my router/switch and controller/WAP configurations against each site to make sure there is a mirror in place.
Any ideas?
SR 617433573

Answer 1

dmantill,
Good morning and thank you for linking in the pdf.
I read it and hit several of the hyperlinks included in the pdf.
While I found the information useful and informative overall I did not really see anything that explained or covered the issue I am encountering.
I have a SR open now and the TAC engineer wants me to capture some debugs on the client mac. Once I can get the local tech onsite again we will perform the connection attempt with the debugging enabled.
FYI this is what the engineer wants to see.
Here is the information that I need to see when the problem occurs:
Disable/Disconnect the wireless client from the network – wait 1-2 mins
Open Telnet/SSH session to the WLC CLI - (Use Putty/SecureCRT with logging enabled)
type: Debug client
Turn the wireless device back on and let it authenticate/associate to the wireless network.  Once the client experiences the problem, disable the debug process using the command: 
debug disable-all
Filename: DebugClient.TXT