Roughly three months ago when iOS 9 was still the newest version available for the iPhone, we encountered a bug in the Twitter iOS app. When doing a transparent proxy setup for one of our iOS app security tests, a Twitter HTTPS request turned up in the Burp proxy log. This should never happen, as the proxy’s HTTPS certificate is not trusted on iOS and therefore connections should be rejected. Being shocked, we checked that certainly we did not install the CA certificate of the proxy on the iPhone and verified with a second non-jailbroken iPhone. The bug was repoducible on iOS 9.3.3 and 9.3.5.
After opening a Hackerone bug report with Twitter I took some time to further investigate the issue. Changing the seemingly unrelated location of the DHCP server in our test setup from the interception device to the WiFi access point made the bug non-reproducible. Moving the DHCP server back to the interception device the issue was reproducible again. This could only mean this was a bug that needed exact timing of certain network related packets. After a lot of back and forth, I was certain that this has to be a race condition/thread safety problem.
Dissecting the network packets with Wireshark, I was able to spot the bug. It seems that if the server certificate in the server hello packet is invalid, the TLS session is not removed fast enough/in a thread safe manner from the TLS connection pool. If the race condition is triggered, this TLS session will be reused for another TLS connection (TLS session resumption). During the TLS session resumption the server hello packet will not include a server certificate. The TLS session is already trusted and the client has no second opportunity to check the server certificate. If an attacker is able to conduct such an attack, the authentication mechanism of TLS is broken, allowing extraction of sensitive OAuth tokens, redirecting the Twitter app via HTTP redirect messages and other traffic manipulations.
I was not able to reproduce the issue on iOS 10. Twitter additionally fixed the issue on their side in Twitter iOS version 6.44, but noted that this was probably related to an Apple bug. We did not further investigate the issue, but the assumption seems plausible.
The issue was rated high severity by Twitter. The entire details are published on Hackerone.
Update: CVE-2016-10511 was assigned to this security issue.