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Transparent SSL Squid Proxy & Mobile Devices

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Hi guys,

I've started building on my pfsense platform to provide additional security features.

One thing I have turned on is the Squid Proxy, and I'm using it in transparent SSL mode with a self signed cert installed on client machines. This all works fine on our client computers, but I am having issues with some apps on mobile devices.

On my iphone the facebook app will not update, although with the cert installed and enabled in certificate services on the device I can browse the internet through safari without issues.

In my org we allow staff to use our wifi with their personal devices, albeit with no access to our local LAN, only DHCP and gateway access, so not sure what I should be doing to troubleshoot, I've looked at the realtime logging when trying to use the app and it looks like my device isn't getting anywhere near the proxy.

I...


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