Apple iOS via Ironport WSA

Question

I'm hoping for some help with trying to authenticate Apple iOS devices via an Ironport S650.
I'm authenticating devices to the corporate network successfully with NPS, however I'm frequently encountering authentication failures.
In the authlogs I am seeing a number of messages such as:
Tue Nov 20 14:08:14 2012 Info: PROX_AUTH : - : Login for user []\[[email protected]]@[DN6FXBA4DFJ1] failed due to [No such user]
Tue Nov 20 14:27:40 2012 Info: PROX_AUTH : - : NTLM CRAP authentication for user [DOMAIN]\[ipad] returned NT_STATUS_INVALID_WORKSTATION (PAM: 7)Tue Nov 20 14:27:40 2012 Info: PROX_AUTH : - : Login for user [DOMAIN]\[ipad]@[DN6FXBA4DFJ1] failed due to [Invalid workstation}
I have configured the iPad to use the proxy server on port 80 and entered a valid username (iPad) and password. On launching Safari, I am repeatedly prompted for a username and password still.
Having done a little more reading, I gather that this is just the first of many issues I may encounter. As such, I'm keen to know if anybody has successfully deployed iPads connecting to the web via an Ironport appliance and if so what you would recommend.
Thanks,
Neil

Answer 1

Hi Neil,
How to process Apple QuickTime (MAC/OSX) requests via Cisco Ironport Web Security
Appliance (WSA) if NTLM authentication is required?
Environment:
Cisco Ironport Web Security Appliance (WSA)
NTLM authentication using the schemes "NTLMSSP" or "Basic or NTLMSSP"
Mac OS X 10.5 (Leopard) / Mac OS X 10.6 (Snow Leopard)
Apple QuickTime (verified 7.6.5 / 7.6.6)
Symptoms:
The Mac OS X version of QuickTime fails to pass the NTLM authentication challenge and to fetch streaming
content via WSA if either the NTLM scheme "NTLMSSP" or "Basic or NTLMSSP"
has been selected. Executing QuickTime in embedded (browser) or standalone mode makes no difference.
Solution:
QuickTime for Mac OS X does not support the NTLM authentication schemes "NTLMSSP" and "Basic or NTLMSSP".
QuickTime will establish connections once one of the following workarounds has been applied:
(A) Disable authentication (Not recommended)
(B) Change the global authentication scheme to NTLM "Basic (only)".
(C) Create an authentication exception for the OSX QuickTime player using the
      custom user agent "QuickTime" or "QuickTime/VERSION" (QuickTime/7.6.6 for example).