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Cisco 5500 Series Controller and 2606 AP's

Good evening everyone, 

I have a problem that our staff and myself have been beating our head against the wall for sometime on, maybe someone here has seen a similar issue.


The problem has many variables so I will try to be as complete and clear as I can. 


Cisco 5500 Series Controller : AIR-CT5508-K9

software version

Cisco 2602 AP's AIR-CAP2602I-A-K9

iOS Version: 15.2(4)JB5$

Dell Venue 11 Tablets  w/ Windows 8.1

k-12 school district 


I have 2 5500 series controllers, call them controller 1 and controller 2,

Controller 1 manages half the district

Controller 2 manages the other half

I can take the dell tablets to a school connected to controller 2 with 2602 AP's and try to connect that device to the ap and i get "checking network requirements" then "Cannot Connect to this Network" 

I can take that same device to an AP on controller 1 at another school and the device will connect without issue. I am broadcasting WPA2 SSID and 802.1x, same behavior on both SSID's 

I can go to the school where I have connection issues (controller 2) and I can move that AP to controller 1 and I cannot connect. 

Also, I can take a 2602 configure it at my desk on controller 2 (the problem controller) and the device will connect. 

Take the same AP to the school site and it will not connect. I can take other windows 7 AND 8.1 clients at this site and they will connect using both the WPA2 and 802.1x SSID.  So I do not believe its a layer 1 or 2 issue at the school, because other devices, including other 8.1 devies and apple devices will connect. I do not believe its a device issue because the device connects without issue at other schools. 

I spent today checking the controller configs line by line and I cant see any difference, all controllers and AP's on the same firmware. 

I realize this is a lot of information, please ask any questions in areas I may be been unclear. 

Looking forward to the responses!

Here are two images from our Prime appliance when the device is trying to connect to the AP 

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