APR-HTTPS enables the capture and the decryption of HTTPS traffic between hosts. It works in conjunction with Cain's Certificate Collector to inject fake certificates into SSL sessions, previously hijacked by mean of APR. Using this trick it is possible to decrypt encrypted data before it arrives to the real destination performing a what so called Man-in-the-Middle attack.

 

Be warned that clients will notice this kind of attack because the server's certificate file injected into the SSL session is a fake one and although it is very similar to the real one it is not signed by a trusted certification authority. When the victim client starts a new HTTPS session, his browser shows a pop-up dialog warning about the problem.

 

 

APR-HTTPS uses the certificate files manipulated by the Certificate Collector. They contains the same parameters of the real ones except for asymmetric encryption keys; this deceives a lot of users to accept the server certificate and continue with the session.

 

 

The lower list in the APR-HTTPS tab contains all the session files that have been captured during the Man-in-the-Middle attack; decrypted data is saved in these text files located under the "HTTPS" subdirectory of the main installation folder.

 

 

How it works

Cain's HTTPS sniffer works in FULL-DUPLEX CLIENT-SIDE STEALTH mode; both server and client traffic is decrypted and if spoofing is enabled the attacker's IP and MAC addresses are never exposed to the victim client. Connections are accepted by a local "acceptor" socket listening on HTTPS port defined in the configuration dialog; this socket handle hijacked client connections but only when APR is enabled. OpenSSL libraries are used to manage SSL communications over two more sockets, one used for the traffic between the client <-> Cain and the other used for the traffic between Cain <-> server.

 

This is how all works step by step:

 

1) The HTTPS filter is enabled by the user in the configuration dialog

2) APR is enabled by the user using the button on the toolbar -> the Man-in-the-Middle attack is ready

3) The victim client starts a new session to an HTTPS enabled server (e.g. https://login.passport.com)

4) Packets from the client are hijacked by APR and captured by Cain's sniffer by mean of Winpcap driver

5) APR-HTTPS search for a fake certificate associated to the requested server in the Certificate Collector; if present the certificate will be used if not it will be automatically downloaded, properly modified and stored locally for future usage .

6) Packets from the victim are modified so that they are re-directed to the local acceptor socket; modifications are made on MAC addresses, IP addresses and TCP source ports (Port Address Translation "PAT" is used to handle multiple connections). The data captured is then sent again into the network using Winpcap but it is this time addressed to the local socket that will accept the Client-side connection.

7) The Server-side socket is created and connected to the real server requested by the victim.

8) OpenSSL libraries are used to manage encryption on both sockets using the fake certificate victim-side and the real certificate sever-side.

9) Packets sent by the Client-side socket are modified again to reach the victim's host.

10) Data coming from the server is decrypted, saved to session files, re-encrypted and sent to the victim host by mean of the Client-side socket.

11) Data coming from the client is decrypted, saved to session files, re-encrypted and sent to the server by mean of the Server-side socket.

 

Although it can be noticed from the fake certificate file used, this kind of attack is STEALTH from a client point of view because the victim thinks to be connected to the real server; try a "netstat -an" on the client to check yourself.

 

Once decrypted, traffic from the client is also sent to the HTTP sniffer filter for a further analysis on credentials. You can take a look at the data saved in session files by APR-HTTPS here.

Prerequisites  

This feature needs APR to be enabled and a Man-in-the-Middle condition between the HTTPS server and the victim host.

Limitations

This feature does not work like a PROXY server; because of the usage of the Winpcap driver it cannot decrypt HTTPS sessions initiated from the local host.

Usage

After you successfully set up APR and enabled the HTTPS sniffer filter, sessions are automatically saved in the HTTPS subdirectory and can be viewed using the relative function within the list pop up menu.