3.7.2 Upward negotiation

Other application protocols⁷ use a different approach to enable the secure layer. They use something often called as the “TLS upgrade” method. This method is quite tricky but it is more flexible. The idea is to extend the application protocol to have a “STARTTLS” request, whose purpose it to start the TLS protocols just after the client requests it. This approach does not require any extra port to be reserved. There is even an extension to HTTP protocol to support this method [RFC2817].

The tricky part, in this method, is that the “STARTTLS” request is sent in the clear, thus is vulnerable to modifications. A typical attack is to modify the messages in a way that the client is fooled and thinks that the server does not have the “STARTTLS” capability. See a typical conversation of a hypothetical protocol:

(client connects to the server)

CLIENT: HELLO I’M MR. XXX

SERVER: NICE TO MEET YOU XXX

CLIENT: PLEASE START TLS

SERVER: OK

*** TLS STARTS

CLIENT: HERE ARE SOME CONFIDENTIAL DATA

And an example of a conversation where someone is acting in between:

(client connects to the server)

CLIENT: HELLO I’M MR. XXX

SERVER: NICE TO MEET YOU XXX

CLIENT: PLEASE START TLS

(here someone inserts this message)

SERVER: SORRY I DON’T HAVE THIS CAPABILITY

CLIENT: HERE ARE SOME CONFIDENTIAL DATA

As you can see above the client was fooled, and was naïve enough to send the confidential data in the clear, despite the server telling the client that it does not support “STARTTLS”.

How do we avoid the above attack? As you may have already noticed this situation is easy to avoid. The client has to ask the user before it connects whether the user requests TLS or not. If the user answered that he certainly wants the secure layer the last conversation should be:

(client connects to the server)

CLIENT: HELLO I’M MR. XXX

SERVER: NICE TO MEET YOU XXX

CLIENT: PLEASE START TLS

(here someone inserts this message)

SERVER: SORRY I DON’T HAVE THIS CAPABILITY

CLIENT: BYE

(the client notifies the user that the secure connection was not possible)

This method, if implemented properly, is far better than the traditional method, and the security properties remain the same, since only denial of service is possible. The benefit is that the server may request additional data before the TLS Handshake protocol starts, in order to send the correct certificate, use the correct password file, or anything else!