SSL/TLS S/MIME

SSL/TLS

  • Secure Socket Layer
  • Transport Layer Security
  • RFC2246

TLS

  • TLS Record Protocol
  • TLS Handshake Protocol

TLS Record Protocol

  • Private
    • Symmetric Cryptography
    • DES, RC4 etc
  • Enhanced Connection Reliability
    • CRC, Checksum ... Ether / TCP
    • HMAC ... Keyed-Hashing for Message Authentication Code
    • MD5, SHA1

TLS Handshake Protocol

  • Peer's Identity Authentication ... Public Key Cryptography
  • Symmetric Algorithm/Key Exchange Negotiation ... Secure and Reliable

Handshake

  • Handshake ... 0x16 (22)
  • Version ... 3, 1
  • Length ... 16bit

ClientHello

  • ClientHello ... (1)
  • Sends Random, SessionID, Cipher Suits, Compression Methods
  • CipherSuit examples
    • 01 = TLS_RSA_WITH_NULL_MD5
    • 05 = TLS_RSA_WITH_RC4_128_SHA

ServerHello

  • ServerHello ... (2)
  • Select CipherSuit and CompressionMethod
  • Selects for example: 
       39 = Ephemeral Diffie-Hellman key exchange using RSA certificate
  • See

Diffie-Hellman key exchange

  • See
  • C->S: A = ga mod p, g, p
  • S->C: B = gb mod p
  • KA = Ab = gab mod p
  • KB = Ba = gba mod p

ChangeCipherSpec

  • Later on, encrypted messages are sent

HTTPS

  • HTTP over TLS/SSL
  • use TLS/SSL from the very start
    • Immediately after TCP connection was established
  • C->S: ClientHello
  • S->C: ServerHello (DHE) ChangeCipherSpec ...
  • C->S: ChangeCipherSpec ...

TLS over POP

  • S->C: +OK Qpopper (version 4.0.18) at is01 starting.
  • C->S: CAPA
  • S->C: +OK Capability list follows
  • S->C: STLS ...
  • C->S: STLS
  • S->C: +OK STLS
  • C->S: ClientHello ...

TLS over SMTP

  • EHLO ... STARTTLS

Server Certificate

  • Server's public key should be signed by a trusted authority
  • CA ... Certificate Authority

SSL Server Setup (1)

  • Compile Apache with SSL enabled
  • You need OpenSSL library and include files
  • --enable-ssl and --with-ssl=DIR options for apache httpd configure command

Server keys

  • Key generation: 
       $ openssl genrsa -out server.key 1024
  • Certficate Request: 
       $ openssl req -new -key server.key -out server.csr
   Country Name (2 letter code) [AU]:JP
   State or Province Name (full name) [Some-State]:Kochi
   Locality Name (eg, city) []:Kochi
   Organization Name (eg, company) [Internet Widgits Pty Ltd]:Kochi University
   Organizational Unit Name (eg, section) []:Information Science
   Common Name (eg, YOUR name) []:www.is.kochi-u.ac.jp
   Email Address []:example@is.kochi-u.ac.jp

Get CA signature

Apache SSL Configuration

  • in httpd.conf (extra/httpd-ssl.conf)
  • SSLEngine on
  • SSLCertificateFile /path/to/server.crt
  • SSLCertificateKeyFile /path/to/server.key
  • etc. etc.

Role of CA

PGP vs PKI

  • PGP ... Pretty Good Privacy
  • PGP -> OpenPGP, GnuPG
  • Peer Signed Public Key
  • PKI ... Public Key Infrastructure
  • PKI -> SSL/TLS, S/MIME
  • Authorized Key Signing

Signing

  • PGP (message.txt -> message.txt.asc): 
       $ gpg --detach-sign -a message.txt
  • S/MIME (message.txt -> mail.msg): 
       $ openssl smime -sign -in message.txt -text -out mail.msg -inkey mykey.pem -signer mycrt.pem

Verifying Signature

  • PGP: 
       $ gpg --verify message.txt.asc
  • S/MIME: 
       $ openssl smime -verify -in mail.msg -CAfile demoCA/cacert.pem
  • Note that signer's public key is included in mail.msg

Encrypting

  • PGP: 
       $ gpg -r tkikuchi@is.kochi-u.ac.jp -ea message.txt
  • S/MIME (message.txt -> encmail.msg): 
       $ openssl smime -encrypt -in message.txt -des3 -out encmail.msg mycrt.pem

Decrypting

  • PGP: 
       $ gpg message.txt.asc
  • S/MIME: 
       $ openssl smime -decrypt -in encmail.msg -recip mycrt.pem -inkey mykey.pem

Miscellaneous Applications

Quiz of the Day

  • Spell out the following acronyms
  • TLS
  • CA