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A second approach to initiate a TLS session is to use the standard TCP port number for the application layer protocol and define a special message in this protocol to trigger the start of the TLS session. This is the solution used for SMTP with the ``STARTTLS`` message. This extension to SMTP :rfc:`3207` defines the new STARTTLS command. The client can issue this command to indicate to the server that it wants to start a TLS session as shown in the example below captured during a session on port 25.
In the remaining parts of this chapter, we assume that the TLS session starts immediately after the establishment of the TCP connection. This corresponds to the deployments on web servers. We focus our presentation of TLS on this very popular use case. TLS is a complex protocol that supports other features than the one used by web servers. A more detailed presentation of TLS may be found in [KPS2002]_ and [Ristic2015]_.
A TLS session is divided in two phases: the handshake and the data transfer. During the handshake, the client and the server negotiate the security parameters and the keys that will be used to secure the data transfer. During the second phase, all the messages exchanged are encrypted and authenticated with the negotiated algorithms and keys.
The TLS handshake
When used to interact with a regular web server, the TLS handshake has three important objectives:
Securely negotiate the cryptographic algorithms that will be used by the client and the server over the TLS session
Verify that the client interacts with a valid server
Securely agree on the keys that will be used to encrypt and authenticate the messages exchanged over the TLS session
The TLS handshake is a four-way handshake illustrated in the figure below.
In a nutshell, the client starts the TLS handshake by proposing a random nonce. The server replies with its random nonce and a certificate that binds its name to a public key. The client generates a MasterSecret that will be used later to derive the session keys and encrypts it with the public key of the server. It also generates a `Finished` message that contains a MAC of all the messages exchanged to allow the server to detect any modification of the messages sent by the client. The server also sends its own `Finished` message. At that point, the client and the server sent encrypted records thanks to the keys derived from the MasterSecret.
Let us first discuss the negotiation of the cryptographic algorithms and parameters. Like all security protocols, TLS includes some agility in its design since new cryptographic algorithms appear over the years and some older algorithms become deprecated once cryptanalysts find flaws. The TLS handshakes starts with the ``ClientHello`` message that is sent by the client. This message carries the following information :
`Protocol version number`: this is the version of the TLS protocol supported by the client. The server should use the same version of the TLS protocol as the client, but may opt for an older version. Both versions 1.2 and 1.3 of TLS are deployed today. Older versions are being deprecated.
`Random number`: security protocols rely on random numbers. The client sends a 32 bytes long random number where usually four of these bytes correspond to the client's clock. This random number is used, together with the server's random number, as a seed to generate the security keys.
`Cipher suites` : this ordered list contains the set of cryptographic algorithms that are supported by the client, with the most preferred one listed first. In contrast with ``ssh`` that allows negotiating independent algorithms for encryption, key exchange and authentication, TLS relies on suites that combine these algorithms together. Many cryptographic suites have been defined for TLS. Various recommendations have been published on the security of some of these suites :rfc:`7525`.
`Compression algorithm` : the client may propose the utilization of a specific compression algorithm (e.g. zlib). In theory, compressing the data before encrypting it is an intelligent way to reduce the amount of data exchanged. Unfortunately, its implementation in TLS has caused several security problems [PHG2013]_. For this reason, compression is usually disabled in TLS :rfc:`7525`.
`Extensions` : TLS supports various extensions in the ``ClientHello`` message. These extensions :rfc:`6066` are important to allow the protocol to evolve, but many of them go beyond the scope of this chapter.
The ``Server Name Indication (SNI)``
The ``Server Name Indication (SNI)`` extension defined in :rfc:`6066` is an important TLS extension for web servers. It is used by the client to indicate the name of the server that it wishes to contact. The IP address associated to this name has been queried from the DNS and used to establish the TCP connection. Why should the client indicate the server name in the TLS ``ClientHello`` ? The motivation is the same as for the ``Host`` header line in HTTP/1.0. With the SNI extension, a single TLS server can support several web sites that use different domain names. Thanks to the SNI extension, the server knows the concerned domain name at the start of the TLS session. Without this extension, hosting providers would have been forced use one IP address per TLS-enabled server.
The server replies to the ``ClientHello`` with several messages:
the ``ServerHello`` message that contains the protocol version chosen by the server (assumed to be the same as the client version in this chapter), the 32 random bytes chosen by the server, the `Cipher Suite` selected by the server from the list advertised by the client and a `Session Id`. This `Session Id` is an identifier which is chosen by the server. It identifies the TLS session and the security parameters (algorithms and keys) negotiated for this session. It is used to support session resumption.
the ``Certificate`` message provides the certificate (or usually a chain of certificates) that binds a domain name to the public key used by the server. TLS uses the server certificates to authenticate the server. It relies on a Public Key Infrastructure that is composed of a set of root certification authorities that issue certificates to certification authorities that in the end issue certificates to servers. TLS clients are usually configured with the public keys of several root certification authorities and use this information to validate the certificates that they receive from servers. For historical reasons, the TLS certificates are encoded in ASN.1 format. The details of the ASN.1 syntax [Dubuisson2000]_ are outside the scope of this book.
the ``ServerKeyExchange`` message is used by the server to transmit the information that is required to perform the key exchange. The content of this message is function of the selected key exchange algorithm.
the ``ServerHelloDone`` indicates that the server has sent all the messages for the first phase of the handshake.
At this point, it is time to describe the TLS key exchange. TLS supports different key exchange mechanisms that can be negotiated as part of the selection of the cipher suite. We focus on two of them to highlight their differences:

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