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Cisco Defense Orchestrator

Troubleshooting SSL Decryption Issues

 

Handling Web Sites Where Decrypt Re-sign Works for a Browser but not an App (SSL or Certificate Authority Pinning)

Some apps for smart phones and other devices use a technique called SSL (or Certificate Authority) pinning. The SSL pinning technique embeds the hash of the original server certificate inside the app itself. As a result, when the app receives the resigned certificate from the Firepower Threat Defense device, the hash validation fails and the connection is aborted.

The primary symptom is that users cannot connect to the web site using the site’s app, but they can connect using the web browser, even when using the browser on the same device where the app fails. For example, users cannot use the Facebook iOS or Android app, but they can point Safari or Chrome at https://www.facebook.com and make a successful connection.

Because SSL pinning is specifically used to avoid man-in-the-middle attacks, there is no workaround. You must choose between the following options:

  • Support app users, in which case you cannot decrypt any traffic to the site. Create a Do Not Decrypt rule for the site’s application (on the Application tab for the SSL Decryption rule) and ensure that the rule comes before any Decrypt Re-sign rule that would apply to the connections.
  • Force users to use browsers only. If you must decrypt traffic to the site, you will need to inform users that they cannot use the site’s app when connecting through your network, that they must use their browsers only.

More Details

If a site works in a browser but not in an app on the same device, you are almost certainly looking at an instance of SSL pinning. However, if you want to delve deeper, you can use connection events to identify SSL pinning in addition to the browser test.

There are two ways an app might deal with hash validation failures:

  • Group 1 apps, such as Facebook, send an SSL ALERT Message as soon as it receives the SH, CERT, SHD message from the server. The Alert is usually an “Unknown CA (48)” alert indicating SSL Pinning. A TCP Reset is sent following the Alert message. You should see the following symptoms in the event details:
    • SSL Flow Flags include ALERT_SEEN.
    • SSL Flow Flags do not include APP_DATA_C2S or APP_DATA_S2C.
    • SSL Flow Messages typically are: CLIENT_HELLO, SERVER_HELLO, SERVER_CERTIFICATE, SERVER_KEY_EXCHANGE, SERVER_HELLO_DONE.
  • Group 2 apps, such as Dropbox, do not send any alerts. Instead they wait until the handshake is done and then send a TCP Reset. You should see the following symptoms in the event:
    • SSL Flow Flags do not include ALERT_SEEN, APP_DATA_C2S, or APP_DATA_S2C.
    • SSL Flow Messages typically are: CLIENT_HELLO, SERVER_HELLO, SERVER_CERTIFICATE, SERVER_KEY_EXCHANGE, SERVER_HELLO_DONE, CLIENT_KEY_EXCHANGE, CLIENT_CHANGE_CIPHER_SPEC, CLIENT_FINISHED, SERVER_CHANGE_CIPHER_SPEC, SERVER_FINISHED.
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