30 Oct 2013 dkg   » (Master)


Many protocols today allow you to upgrade to TLS from within a cleartext version of the protocol. This often falls under the rubric of "STARTTLS", though different protocols have different ways of doing it.

I often forget the exact steps, and when i'm debugging a TLS connection (e.g. with tools like gnutls-cli i need to poke a remote peer into being ready for a TLS handshake. So i'm noting the different mechanisms here. lines starting with C: are from the client, lines starting with S: are from the server.

many of these are (roughly) built into openssl s_client, using the -starttls option. Sometimes this doesn't work because the handshake needs tuning for a given server; other times you want to do this with a different TLS library. To use the techniques below with gnutls-cli from the gnutls-bin package, just provide the --starttls argument (and the appropriate --port XXX argument), and then hit Ctrl+D when you think it's ok to start the TLS negotiation.


The polite SMTP handshake (on port 25 or port 587) that negotiates a TLS upgrade looks like:
C: EHLO myhostname.example
S: [...]
S: [...]
S: 250 [somefeature]
S: 220 2.0.0 Ready to start TLS
<Client can begin TLS handshake>


The polite IMAP handshake (on port 143) that negotiates a TLS upgrade looks like:
S: OK [CAPABILITY IMAP4rev1 [...] STARTTLS [...]] [...]
S: A OK Begin TLS negotiation now
<Client can begin TLS handshake>


The polite POP handshake (on port 110) that negotiates a TLS upgrade looks like:
S: +OK POP3 ready
S: +OK Begin TLS 
<Client can begin TLS handshake>


The polite XMPP handshake (on port 5222 for client-to-server, or port 5269 for server-to-server) that negiotiates a TLS upgrade looks something like (note that the domain requested needs to be the right one):
C: <?xml version="1.0"?><stream:stream to="example.net"
C:  xmlns="jabber:client" xmlns:stream="http://etherx.jabber.org/streams" version="1.0">
S: <?xml version='1.0'?>
S: <stream:stream
S:  xmlns:db='jabber:server:dialback'
S:  xmlns:stream='http://etherx.jabber.org/streams'
S:  version='1.0'
S:  from='example.net'
S:  id='d34edc7c-22bd-44b3-9dba-8162da5b5e72'
S:  xml:lang='en'
S:  xmlns='jabber:server'>
S: <stream:features>
S: <dialback xmlns='urn:xmpp:features:dialback'/>
S: <starttls xmlns='urn:ietf:params:xml:ns:xmpp-tls'/>
S: </stream:features>
C: <starttls xmlns="urn:ietf:params:xml:ns:xmpp-tls" id="1"/>
S: <proceed xmlns='urn:ietf:params:xml:ns:xmpp-tls'/>
<Client can begin TLS handshake>
I don't know (but would like to) how to do:
  • postgresql TLS negotiation
  • mysql TLS negotiation
  • other reasonable network protocols capable of upgrade
  • other free TLS wrapping tools like openssl s_client or gnutls-cli that can start off in the clear and negotiate to TLS. I am trying to get libNSS's tstclnt into the libnss3-tools package, but that hasn't happened yet.
If you know other mechanisms, or see bugs with the simple handshakes i've posted above, please let me know either by e-mail or on the comments here.

Other interesting notes: RFC 2817, a not-widely-supported mechanism for upgrading to TLS in the middle of a normal HTTP session.

Syndicated 2013-10-30 17:00:00 from Weblogs for dkg

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