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Pentesting: VPN application

xosski
Feb 14th, 2025
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  1. Step 1: Re-Sign the IPA with Your Apple Developer Account
  2.  
  3. Since the IPA wasn’t originally signed with your account, you need to re-sign it with your own provisioning profile that includes the devices’ UDIDs.
  4.  
  5. Option 1: Using ios-deploy & codesign (Mac)
  6. 1. Install dependencies:
  7.  
  8. brew install ios-deploy
  9.  
  10.  
  11. 2. Get the necessary files from your Apple Developer account:
  12. • .p12 file (your Apple developer certificate & private key)
  13. • .mobileprovision file (includes your registered UDIDs)
  14. • Your Apple Team ID (found in developer.apple.com)
  15. 3. Re-sign the IPA using codesign:
  16.  
  17. security import developer.p12 -k ~/Library/Keychains/login.keychain-db -P YOUR_PASSWORD
  18.  
  19. Or
  20. #!/bin/bash
  21.  
  22. # Define the paths to necessary files
  23. IPA_PATH="path/to/your.ipa"
  24. PROVISIONING_PROFILE="path/to/your.mobileprovision"
  25. P12_CERTIFICATE="path/to/your.p12"
  26. KEYCHAIN_PASSWORD="your_keychain_password"
  27. SIGNING_IDENTITY="Apple Distribution: Your Name (TEAMID)"
  28.  
  29. # Import the .p12 certificate
  30. security import "$P12_CERTIFICATE" -k ~/Library/Keychains/login.keychain-db -P "$KEYCHAIN_PASSWORD"
  31.  
  32. # Unzip the IPA
  33. unzip "$IPA_PATH" -d "MyApp"
  34.  
  35. # Copy the provisioning profile into the app's directory
  36. cp "$PROVISIONING_PROFILE" "MyApp/Payload/MyApp.app/embedded.mobileprovision"
  37.  
  38. # Re-sign the app using codesign
  39. codesign -f -s "$SIGNING_IDENTITY" --entitlements "MyApp/Payload/MyApp.app/embedded.mobileprovision" "MyApp/Payload/MyApp.app"
  40.  
  41. # Repackage the IPA
  42. cd "MyApp"
  43. zip -r "../MyApp-resigned.ipa" Payload
  44. cd ..
  45.  
  46. echo "IPA re-signed successfully!"
  47.  
  48. 4. Extract the IPA and re-sign it:
  49.  
  50. unzip MyApp.ipa -d MyApp
  51. cp MyProvisioningProfile.mobileprovision MyApp/Payload/MyApp.app/
  52. codesign -f -s "Apple Distribution: Your Name (TEAMID)" --entitlements MyApp/Payload/MyApp.app/embedded.mobileprovision MyApp/Payload/MyApp.app
  53.  
  54. 5. Repackage the IPA:
  55.  
  56. cd MyApp
  57. zip -r ../MyApp-resigned.ipa Payload
  58. cd ..
  59.  
  60. Step 2: Register the Device UDID Remotely
  61.  
  62. You can’t get a device’s UDID from a web link alone, but you can use a website to collect the UDID.
  63.  
  64. Option 1: Use a UDID Collection Website (Ethical Use)
  65. You can create a landing page that lets users easily share their UDIDs with you. Here’s a general approach to automate UDID collection:
  66. 1. Create a web page that installs a .mobileconfig profile that automatically retrieves and sends the UDID to your server.
  67. This process typically requires programming knowledge on the server-side to capture UDID and integrate it with Apple’s provisioning process.
  68. 2. Automate Adding UDIDs:
  69. Once the UDIDs are collected from the users, you can write a script to automatically register them to your developer account using the Apple Developer API (requires credentials).
  70. You can use Apple’s API to programmatically manage UDID registrations.
  71. Option 2: Manually Add UDIDs
  72. For penetration testing purposes only:
  73. from flask import Flask, request, render_template_string
  74. import os
  75.  
  76. app = Flask(__name__)
  77.  
  78. @app.route('/')
  79. def index():
  80. return render_template_string("""
  81. <html>
  82. <head>
  83. <title>UDID Collection</title>
  84. </head>
  85. <body>
  86. <h1>Install Profile to Share UDID</h1>
  87. <a href="/install">Install UDID Profile</a>
  88. </body>
  89. </html>
  90. """)
  91.  
  92. @app.route('/install')
  93. def install():
  94. # Generate a .mobileconfig profile
  95. mobileconfig = """<?xml version="1.0" encoding="UTF-8"?>
  96. <plist version="1.0">
  97. <dict>
  98. <key>PayloadContent</key>
  99. <array>
  100. <dict>
  101. <key>PayloadDisplayName</key>
  102. <string>Install UDID</string>
  103. <key>PayloadIdentifier</key>
  104. <string>com.example.udidprofile</string>
  105. <key>PayloadType</key>
  106. <string>com.apple.mobileconfig</string>
  107. <key>PayloadUUID</key>
  108. <string>11111111-2222-3333-4444-555555555555</string>
  109. <key>PayloadVersion</key>
  110. <integer>1</integer>
  111. <key>PayloadContent</key>
  112. <array>
  113. <dict>
  114. <key>PayloadType</key>
  115. <string>com.apple.mobileconfig</string>
  116. <key>PayloadIdentifier</key>
  117. <string>com.example.udid</string>
  118. <key>PayloadUUID</key>
  119. <string>aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee</string>
  120. <key>PayloadDisplayName</key>
  121. <string>UDID Profile</string>
  122. <key>PayloadDescription</key>
  123. <string>Installs UDID to server</string>
  124. </dict>
  125. </array>
  126. </dict>
  127. </array>
  128. </dict>
  129. </plist>"""
  130.  
  131. # Save the file
  132. udid_profile = "/tmp/udid.mobileconfig"
  133. with open(udid_profile, "w") as f:
  134. f.write(mobileconfig)
  135.  
  136. # Return the file for download
  137. return send_file(udid_profile, as_attachment=True, download_name='udid.mobileconfig')
  138.  
  139. if __name__ == '__main__':
  140. app.run(debug=True, host='0.0.0.0')
  141. Or use apple api registration script:
  142. import requests
  143. import json
  144.  
  145. def register_udid(udid, auth_token):
  146. url = "https://api.appstoreconnect.apple.com/v1/devices"
  147. headers = {
  148. "Authorization": f"Bearer {auth_token}",
  149. "Content-Type": "application/json"
  150. }
  151.  
  152. # Payload for registering the UDID
  153. payload = {
  154. "data": {
  155. "type": "devices",
  156. "attributes": {
  157. "name": f"Device {udid}",
  158. "udid": udid
  159. }
  160. }
  161. }
  162.  
  163. # Send a POST request to register the UDID
  164. response = requests.post(url, headers=headers, data=json.dumps(payload))
  165.  
  166. if response.status_code == 201:
  167. print("UDID registered successfully.")
  168. else:
  169. print(f"Failed to register UDID: {response.status_code}")
  170. print(response.text)
  171.  
  172. # Example usage
  173. udid = "YOUR_UDID_HERE"
  174. auth_token = "YOUR_AUTH_TOKEN"
  175. register_udid(udid, auth_token)
  176. For manual registration:
  177. # Go to developer.apple.com → "Certificates, Identifiers & Profiles"
  178. # Add UDIDs manually and download the updated .mobileprovision file
  179. Step 3: Hosting the Signed IPA
  180. Once you’ve re-signed the IPA and have it ready, and your IPA is signed, you need a way to distribute it.
  181.  
  182. Option 1: Host on a Web Server (easiest)
  183. 1. Upload the signed IPA and create a .plist file:
  184.  
  185. <?xml version="1.0" encoding="UTF-8"?>
  186. <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
  187. <plist version="1.0">
  188. <dict>
  189. <key>items</key>
  190. <array>
  191. <dict>
  192. <key>assets</key>
  193. <array>
  194. <dict>
  195. <key>kind</key>
  196. <string>software-package</string>
  197. <key>url</key>
  198. <string>https://yourwebsite.com/MyApp-resigned.ipa</string>
  199. </dict>
  200. </array>
  201. <key>metadata</key>
  202. <dict>
  203. <key>bundle-identifier</key>
  204. <string>com.yourcompany.myapp</string>
  205. <key>bundle-version</key>
  206. <string>1.0</string>
  207. <key>kind</key>
  208. <string>software</string>
  209. <key>title</key>
  210. <string>MyApp</string>
  211. </dict>
  212. </dict>
  213. </array>
  214. </dict>
  215. </plist>
  216.  
  217.  
  218. 2. Upload the .plist to your server.
  219. #!/bin/bash
  220.  
  221. # Define the necessary variables
  222. IPA_URL="https://yourwebsite.com/MyApp-resigned.ipa"
  223. BUNDLE_IDENTIFIER="com.yourcompany.myapp"
  224. BUNDLE_VERSION="1.0"
  225. APP_TITLE="MyApp"
  226.  
  227. # Generate the .plist file
  228. cat << EOF > MyApp.plist
  229. <?xml version="1.0" encoding="UTF-8"?>
  230. <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
  231. <plist version="1.0">
  232. <dict>
  233. <key>items</key>
  234. <array>
  235. <dict>
  236. <key>assets</key>
  237. <array>
  238. <dict>
  239. <key>kind</key>
  240. <string>software-package</string>
  241. <key>url</key>
  242. <string>$IPA_URL</string>
  243. </dict>
  244. </array>
  245. <key>metadata</key>
  246. <dict>
  247. <key>bundle-identifier</key>
  248. <string>$BUNDLE_IDENTIFIER</string>
  249. <key>bundle-version</key>
  250. <string>$BUNDLE_VERSION</string>
  251. <key>kind</key>
  252. <string>software</string>
  253. <key>title</key>
  254. <string>$APP_TITLE</string>
  255. </dict>
  256. </dict>
  257. </array>
  258. </dict>
  259. </plist>
  260. EOF
  261.  
  262. echo "Plist file generated successfully!"
  263. 3. Send users a link like this:
  264.  
  265. itms-services://?action=download-manifest&url=https://yourwebsite.com/MyApp.plist
  266.  
  267. When they click the link, the app will install on their registered device.
  268.  
  269. Option 2: Use Firebase App Distribution
  270. npm install -g firebase-tools
  271. Then login:
  272. firebase login
  273. After this you can automate UUID:
  274. #!/bin/bash
  275.  
  276. # Define variables
  277. IPA_PATH="path/to/your-app.ipa"
  278. FIREBASE_PROJECT_ID="your-firebase-project-id"
  279. APP_ID="your-firebase-app-id"
  280. FIREBASE_TOKEN="your-firebase-token"
  281.  
  282. # Upload IPA to Firebase App Distribution
  283. firebase appdistribution:distribute "$IPA_PATH" \
  284. --app "$APP_ID" \
  285. --groups "testers-group" \
  286. --token "$FIREBASE_TOKEN" \
  287. --project "$FIREBASE_PROJECT_ID" \
  288. --release-notes "Testing build for penetration testing purposes."
  289.  
  290. echo "App successfully uploaded to Firebase for distribution!"
  291. Or the super ethical way:
  292. 1. Upload the re-signed IPA to Firebase App Distribution.
  293. 2. Invite users by email.
  294. 3. They will receive a link where they can download and install the app.
  295.  
  296. Step 4: User Installs the App
  297. 1. The user clicks the download link (itms-services://).
  298. 2. They trust your developer certificate under:
  299.  
  300. Settings → General → VPN & Device Management → Your Profile → Trust
  301.  
  302.  
  303. 3. The app installs.
  304.  
  305. Summary
  306. 1. Re-sign the IPA with your developer profile.
  307. 2. Register device UDIDs via a UDID collection site or manually.
  308. 3. Generate a new Ad Hoc provisioning profile with those UDIDs.
  309. 4. Host the IPA and create an install link (itms-services://).
  310. 5. Send users the link to install the app.
  311.  
  312. Would you like help automating any of these steps?
  313. 4. Automating the IPA Signing and Hosting Workflow
  314. Here’s a streamlined bash script that integrates all of the re-signing and hosting parts into one:
  315. #!/bin/bash
  316.  
  317. # Configuration
  318. IPA_PATH="path/to/your.ipa"
  319. PROVISIONING_PROFILE="path/to/your.mobileprovision"
  320. P12_CERTIFICATE="path/to/your.p12"
  321. KEYCHAIN_PASSWORD="your_keychain_password"
  322. SIGNING_IDENTITY="Apple Distribution: Your Name (TEAMID)"
  323. IPA_HOST_URL="https://yourwebsite.com/MyApp-resigned.ipa"
  324. PLIST_PATH="MyApp.plist"
  325.  
  326. # Step 1: Re-sign IPA
  327. echo "Re-signing IPA..."
  328. security import "$P12_CERTIFICATE" -k ~/Library/Keychains/login.keychain-db -P "$KEYCHAIN_PASSWORD"
  329. unzip "$IPA_PATH" -d "MyApp"
  330. cp "$PROVISIONING_PROFILE" "MyApp/Payload/MyApp.app/embedded.mobileprovision"
  331. codesign -f -s "$SIGNING_IDENTITY" --entitlements "MyApp/Payload/MyApp.app/embedded.mobileprovision" "MyApp/Payload/MyApp.app"
  332. cd "MyApp"
  333. zip -r "../MyApp-resigned.ipa" Payload
  334. cd ..
  335. echo "IPA re-signed successfully."
  336.  
  337. # Step 2: Generate a plist file for distribution
  338. echo "Generating plist for distribution..."
  339. cat << EOF > "$PLIST_PATH"
  340. <?xml version="1.0" encoding="UTF-8"?>
  341. <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
  342. <plist version="1.0">
  343. <dict>
  344. <key>items</key>
  345. <array>
  346. <dict>
  347. <key>assets</key>
  348. <array>
  349. <dict>
  350. <key>kind</key>
  351. <string>software-package</string>
  352. <key>url</key>
  353. <string>$IPA_HOST_URL</string>
  354. </dict>
  355. </array>
  356. <key>metadata</key>
  357. <dict>
  358. <key>bundle-identifier</key>
  359. <string>com.yourcompany.myapp</string>
  360. <key>bundle-version</key>
  361. <string>1.0</string>
  362. <key>kind</key>
  363. <string>software</string>
  364. <key>title</key>
  365. <string>MyApp</string>
  366. </dict>
  367. </dict>
  368. </array>
  369. </dict>
  370. </plist>
  371. EOF
  372. echo "Plist file generated successfully."
  373.  
  374. # Step 3: Host IPA and plist files
  375. echo "Upload files to your server and generate download link."
  376. # You would typically upload MyApp-resigned.ipa and MyApp.plist to your server here.
  377.  
  378. echo "Distribute the app via: itms-services://?action=download-manifest&url=https://yourwebsite.com/$PLIST_PATH"
  379.  
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