Opportunistic TLS

Opportunistic TLS refers to extensions in plain text communication protocols, which offer a way to upgrade a plain text connection to an encrypted (TLS or SSL) connection instead of using a separate port for encrypted communication. Several protocols use a command named "STARTTLS" for this purpose. It is primarily intended as a countermeasure to passive monitoring.

The STARTTLS command for IMAP and POP3 is defined in RFC 2595, for SMTP in RFC 3207, for XMPP in RFC 6120 and for NNTP in RFC 4642. For IRC, the de facto definition is documented at the InspIRCd Wiki.^[1] FTP uses the command "AUTH TLS" defined in RFC 4217 and LDAP defines a protocol extension OID in RFC 2830.

Layering

TLS is application-neutral; in the words of RFC 5246:

One advantage of TLS is that it is application protocol independent. Higher-level protocols can layer on top of the TLS protocol transparently. The TLS standard, however, does not specify how protocols add security with TLS; the decisions on how to initiate TLS handshaking and how to interpret the authentication certificates exchanged are left to the judgment of the designers and implementors of protocols that run on top of TLS.^[2]

The style used to specify how to use TLS matches the same layer distinction that is also conveniently supported by several library implementations of TLS. E.g., the RFC 3207 SMTP extension illustrates with the following dialog how a client and server can start a secure session:^[3]

  S: <waits for connection on TCP port 25>
  C: <opens connection>
  S: 220 mail.example.org ESMTP service ready
  C: EHLO client.example.org
  S: 250-mail.example.org offers a warm hug of welcome
  S: 250 STARTTLS
  C: STARTTLS
  S: 220 Go ahead
  C: <starts TLS negotiation>
  C & S: <negotiate a TLS session>
  C & S: <check result of negotiation>
  C: EHLO client.example.org[4]
  . . .

The last EHLO command above is issued over a secure channel. Note that authentication is optional in SMTP, and the omitted server reply may now safely advertise an AUTH PLAIN SMTP extension, which is not present in the plain-text reply.

SSL ports

Before opportunistic TLS was well established, a number of TCP ports were defined for SSL-secured versions of well-known protocols. These establish secure communications and then present a communication stream identical to the old un-encrypted protocol. These are no longer recommended, since opportunistic TLS makes more efficient use of scarce port numbers and allows simpler device configuration. On the other hand, SSL ports have the advantage of fewer round-trips; also less meta-data is transmitted in unencrypted form.^[5] Some examples include:

Weaknesses and mitigations

Opportunistic TLS is an opportunistic encryption mechanism. Because the initial handshake takes place in plain text, an attacker in control of the network can modify the server messages via a man-in-the-middle attack to make it appear that TLS is unavailable (called a STRIPTLS attack). Most SMTP clients will then send the email and possibly passwords in plain text, often with no notification to the user. In particular, many SMTP connections occur between mail servers, where user notification is not practical.

In September 2014, two ISPs in Thailand were found to be doing this to their own customers.^[7][8] In October 2014, Aio Wireless, then a subsidiary of Cricket Wireless, was found to be doing this to their customers.^[9][10]

STRIPTLS attacks can be blocked by configuring SMTP clients to require TLS for outgoing connections (for example, the Exim Message transfer agent can require TLS via the directive "hosts_require_tls" ^[11]). However, since not every mail server supports TLS, it is not practical to simply require TLS for all connections.

This problem is addressed by DNS-based Authentication of Named Entities (DANE), a part of DNSSEC, and in particular by RFC 7672 for SMTP. DANE allows to advertise support for secure SMTP via a TLSA record. This tells connecting clients they should require TLS, thus preventing STRIPTLS attacks. The STARTTLS Everywhere project from the Electronic Frontier Foundation works in a similar way. However, DNSSEC due to deployment complexities and peculiar criticism,^[12] faced a low adoption rate and a new protocol called SMTP Strict Transport Security or SMTP STS has recently been drafted by a group of major email service providers including Microsoft, Google and Yahoo. SMTP STS does not requires the use of DNSSEC to authenticate DANE TLSA records but relies on the certificate authority (CA) system and a trust-on-first-use (TOFU) approach to avoid interceptions. The TOFU model allows a degree of security similar to that of HPKP, reducing the complexity but without the guarantees on first use offered by DNSSEC. In addition, SMTP STS introduces a mechanism for failure reporting and a report-only mode, enabling progressive roll-out and auditing for compliance.

Popularity

Following the revelations made by Edward Snowden in light of the global mass surveillance scandal, popular email providers have bettered their email security by enabling STARTTLS.^[13] Facebook reported that after enabling STARTTLS and encouraging other providers to do the same, 95% of Facebook's outbound email is encrypted with both Perfect Forward Secrecy and strict certificate validation.^[14]

References

External links

• SMTP TLS Tests and Tools (the "Receiver Test" shows dialogs like the one above)
• Verify if a receiving domain has STARTTLS enabled for email and with which security level