iOS13 public beta7 have problem with Charles certificate and unable to SSL proxying

9
votes

Everything is fine when my iPhone 7 is still iOS 12. After it upgrade to iOS13 public beta7, I found that my iPhone can not do SSL proxying with Charles 3.x version.

Charles says:

SSLHandshake: Remote host closed connection during handshake

You may need to configure your browser or application to trust the Charles Root Certificate. See SSL Proxying in the Help menu.

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3
charles-proxyios13
I have to ask, because you don't clarify in your question: did you trust the Charles Root Certificate? charlesproxy.com/documentation/using-charles/ssl-certificates – Lluís Suñol
Of cause I do trust certificate and iPhone could do SSL proxying when it's runing iOS12 – Yan Li
Could be related to new SSL requirements in iOS 13: support.apple.com/en-us/HT210176 (After all, this sort of middle-manning is exactly what such technology is intended to prevent!) – Lightness Races in Orbit
There is no "3.x version". What actual version are you running? 4 came out three years ago - did you try upgrading? Did you try asking the developer? – Lightness Races in Orbit

3 Answers

5
votes

Follow the steps given by the Charles. Steps from Charles After granting trust to the Charles certificate, need to do 1 more step, to enable full trust: https://support.apple.com/en-nz/HT204477

Instruction from Apple

4
votes

Far as I know, Apple has released new security requirements for TLS server certificates in iOS 13 and macOS 10.15. Thus, your Charles CA Root Certificate might be out-of-date. I think you could try to delete that certificate and re-install and trust Charles CA with the newest version of Charles to see if it works (Hope that Charles has updated and fixed this bug). I had switched from Charles to Proxyman and they also had a release to fix this bug: https://github.com/ProxymanApp/Proxyman/releases/tag/1.4.4.1

0
votes

The same issue on iOS 14.3. My solution was reinstalling the certificate. This requires regenerating Root certificate in Charles, which would prompt to install a new one when visiting chls.pro/ssl Recently I reset the device to factory settings, and maybe this caused this error to appear.