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Assessing iOS Applications – setting up a test environment and grabbing low hanging fruit

Thisguide should serve as an introduction for those wishing to get into iOSapplication security testing. It demonstrates grabbing low hanging fruit. Thisguide will not cover all aspects of iOS application security and thereforeshould not be used as a fully fledged methodology. The line between webapplication assessments and mobile assessments is blurred as both consist ofclient/server models and most apps (if not all) speak HTTP (and hopefully someHTTPS). Many of the vulnerabilities you find will therefore require anintelligent web application security specialist's brain behind that Burp proxy.Incidentally, we have tons of them here at SpiderLabs! :)

Alas, let's get on with the show.


1x Jailbroken iPhone/iPad (Cydia)

1x Macbook Pro (to create a wireless network) OR a wirelessnetwork

1x Burp
 Proxy (or similar)

1x Self-signed Certificate (to MiTM HTTPS traffic)

Prepare iPhone/iPad

Cydia should already be installed if the device is jailbroken. OpenCydia, select Sources and add a new source; "http://cydia.hackulo.us".


Install OpenSSH, Installous 4 and Clutch.

Installing the app

If the app is on iTunes then this is easy - find it on the AppStore, download, sync device. If the app isn't on iTunes then the likelihood isthat your client will send you a .IPA file. You can double click this file andit will load in iTunes - sync device as before.

WARNING: iTunes may force you to wipe the device if it issynced with another computer. If so, there is a way around this that doesn'tinvolve syncing. Don't click on the .IPA and don't open iTunes. Instead, scpthe .IPA file over to /User/Documents/Installous/Downloads/ on thedevice and install that way using Installous.

If your client sends you a .XCArchive package, don't worry,not all is lost. Assuming you're on OS X, sort out your Xcode path else you'llget this error.

Error: No developer directory foundat /Developer. Run /usr/bin/xcode-select to update the developer directorypath.

To fix, do thefollowing:

sudo xcode-select -switch/Applications/Xcode.app/Contents/Developer

Now go to your .XCArchive file, right click and"Show Package Contents" and navigate to where the iOS .app file is - jot thisdown, you'll need it for the next bit.

Now armed with the .app file location you canbust out xcrun (our magic wand in this case) and create the .IPA file/package.Replace the path to your .app (what you jotted down before) in the commandbelow. Note to specify "-sdk iphoneos" even if it is for the iPad.

/usr/bin/xcrun -sdk iphoneos PackageApplication"/absolute/path/to/MyApp.xcarchive/Products/Applications/MyApp.app"-o "/absolute/path/to/MyApp.ipa"

You can now scp the .IPA to your iPad and use Installous (withinCydia) to install as usual.

Finding the app

SSHto the device, the app will be installed in /var/mobile/Applications/<ID>/.

HINT: Look for the date when trying to locate the app, or justdo a find.

Connect to the wireless network

Connect the device to the wireless network - be it the MacbookPro's "Internet Sharing" wireless network or an actual wirelessnetwork. Ensure that the Macbook Pro which will intercept requests/responses(via Burp) is on the same network.

Install the self-signed certificate

On the intercepting Macbook Pro we will export Burp'scertificate via Firefox. Set Burp up as a proxy on TCP port 8080 (listening onALL interfaces). Open Firefox, visit any HTTPS site, view the exceptionmessage, view certificate, highlight "PortSwigger CA" in thecertificate hierarchy and not the site. Export as .CER. Mail it to yourself,open the e-mail on the device, click on the attachment and install it.

Important: Make sure you export the "PortSwigger CA" line itemand not the random website below (twitter.com in this case).


Setting up the proxy

Ensure that Burp is listening on ALL interfaces, or at leastone that the device could see over the network. On the device, go to Network,Wi-Fi, click on the blue arrow to the right of the connected wireless network,scroll down to "HTTP Proxy" and select Manual. Insert the details ofthe Macbook Pro with Burp running, IP and TCP port 8080.


Testing the proxy works

Open Safari on the device and test that Burp captures the HTTPtraffic correctly. If it works then load up the iOS application and you will beable to see traffic.


Decrypting apps from iTunes

If you downloaded your client's app from iTunes then you willneed to remove the encryption before you analyse it with strings, etc. Toremove iTunes encryption you can use gdb, or you can use an app called Clutch(which you installed earlier in Cydia). Clutch puts cracked apps in /var/root/Documents/Cracked/.Scp the .IPA file off the device to the Macbook Pro to analyse.

Looking for strings in the binary

Unzip the .IPA file (it's a package really) that you receivedfrom the previous step. Go to the extracted folder, e.g./BAH.app/<BAH> and use "strings" on the binary: stringsBAH > stringsdump.txt. Review stringsdump.txt for any useful stuff.HINT: grep "password", "secret", "http://","encrypt", etc, etc.


Looking at classes, objects, libraries

Use class-dump against the binary and discover information: ./class-dumpbinary or otool: ./otool -ov binary. Things here will becomeuseful during runtime manipulation - variables, view classes, etc.


App files

Apps are installed in /var/mobile/Applications/<ID>/.Inside <APP>.app are application resource files including the binary.Have a look for cached data, databases, etc. A typical app file structure lookslike:







various .plist files

various .sqlite files


Apple's Keychain also worth a look for sensitivedata relating to the app: /var/Keychains/keychain-2.db. Use the KeychainDumper tool at https://github.com/ptoomey3/Keychain-Dumper/blob/master/keychain_dumper to dump allKeychain items (using a wildcard entitlements.xml). If you don't trust thebinary you can also download the source and build it yourself.


What I covered is finding low hanging fruit. Testing past thispoint will depend on what the app does, its complexity, etc. A lot of testingcan be done via Burp as it will interface with web services in many cases,speak HTTP(S) (JSON goodness) and the OWASP Top 10 will apply. Other things to lookfor; how the app is sent to the background (snapshots), file protection, how ituses the pasteboard, how input/output is handled (UIWebView), etc. There isalso a whole world related to runtime manipulation... another blog post!