I have figured it out.
The problem is fairly easy to understand once you understand how iOS treats SSL certificates.
The main problem with the interception was that iOS was not "happy enough" with the SSL cert that was injected. It's main problem was that it that the cert was going beyond iOS' "this is kinda weird but meh okay" threshold and therefore would think a MITM attack was tacking place and just straight up killed the connection during the TLS handshake (I know this because people using charles proxy got that error code and reported it).
The solution to this is fairly easy. iOS doesn't like the cert we inject because it doesn't come from a "trusted" source. Yeah well why don't we just make it a trusted source then
In order to do that I downloaded
Apples Configurator.
I thought to make iOS even more believe this is legit traffic via a legit TLS cert I make inject the root cert via a
mobileconf (it's just another fancy way of Apple saying its an XML file ).
So. Let's go ahead and do ourself a favor shall we
Open the Apple Configurator app and create a new config file (prepare).
On the installation tab disable the "Update iOS" since we don't want to go all that. We just want to inject the cert.
You then go into the "Installation" tab and under "Settings" you select the certificate.
Since we can't include a .pem file in this mobileconf we have to convert our root cert into a .cert file and since it already is in the keychain app just go and export it as an .cert file somewhere where you can easily find it.
Back in the Apple Configurator app you select the just exported .cert root certificate and push the mobileconfig onto your phone via USB cable.
You will be prompted to accept that this is being installed since it is a "untrusted" root cert and afterwards you go through the steps explained by the creator
here in order to install the .pem certificate onto the device. Once there you can setup the proxy just like you would do for a http proxy in the networking settings and see all the TLS encrypted traffic flow in on iOS 8
Happy hacking everyone