If you want to test your iOS penetration testing skills, I recommend that you give Damn Vulnerable iOS Application (DVIA) a try.
DVIA, developed by Indian security expert Prateek Gianchandani, has been created so that it’s riddled with a lot of vulnerabilities, particularly the most common issues found in iOS apps.
The list of security holes includes client-side injection, insecure data storage, runtime manipulation, jailbreak detection, TLS, information disclosure, application patching and broken cryptography.
The current version of DVIA contains flaws tested for iOS versions up to 7.0.4.
You can download Damn Vulnerable iOS Application from the damnvulnerableiosapp.com website. The app itself is free, but if you want the solutions for the challenges, you’ll have to pay $59 (€43). It’s worth noting that you need a jailbroken device in order to use DVIA.