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Im pointing my iPad to be we sense cloud service by configuring it as a proxy in my iPad settings. I'm also specifying my user/pass in the proxy settings.
Internet access is fine but when logging into iCooud I get an SSL error. Any ideas?
You'll need to do a bit more triaging to get anywhere with this...
1) does the problem also exist when not pointed to the Websense cloud service?
if it doesn't, this doesn't necessarily mean that the problem is on the websense side. Could just be that you're hitting a different icloud servicer..
2) what is the specific error message?
3) Do you have the SSL decryption feature enabled or not?