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iOS 8 Proxy Settings and Self-Signed Certificates
Posted by Dustin Hoeppner, Last modified by on 06 February 2015 10:25 AM

Apple devices running iOS 8 will not accept untrusted or otherwise "bad" certificates over proxy settings. The device will not prompt you to accept the certificate or proceed; it just reports that there was an error connecting. However, this is misleading; the device has actually connected, but it silently refuses the certificate without informing the user.

iOS 7 has no issue. iOS 8 has no issue with proxy disabled.


In iOS 8, to use portal over proxy, your options are:

1) Purchase a valid portal certificate from a reputable certificate authority.

2) Generate a self-signed SSL decryption certificate and deploy it via an MDM to the device. This will allow the device to successfully access the Cipafilter's portal. (SSL decryption is not required. The same SSL certificate is used for both SSL Decryption and the captive portal system, unless a third-party certificate has been purchased for use with the portal.) Please see our article on SSL Configuration from the SSL Decryption tab of Internet Filtering -> Content Filtering.

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