Sending mail via SMTP using TLS

It requires configuring the email servers with valid SSL certification to configure them with SMTP TLS.

Sending mail via SMTP using TLS
  1. Become an administrator.

    For more information, see Using Your Assigned Administrative Rights in Securing Users and Processes in Oracle Solaris 11.2 .

  2. Stop sendmail.
    # svcadm disable -t network/smtp:sendmail
  3. Set up the certificates that enable sendmail to use TLS.
    1. Complete the following:
      # cd /etc/mail
      # mkdir -p certs/CA
      # cd certs/CA
      # mkdir certs crl newcerts private
      # echo "01" > serial
      # cp /dev/null index.txt
      # cp /etc/openssl/openssl.cnf .
    2. Use your preferred text editor to change the dir value in the openssl.cnf file from /etc/openssl to /etc/mail/certs/CA.
    3. Use the openssl command-line tool to implement TLS.

      Note that the following command line generates interactive text.

      # openssl req -new -x509 -keyout private/cakey.pem -out cacert.pem -days 365 \
      -config openssl.cnf
      Generating a 1024 bit RSA private key
      .....................................++++++
      .....................................++++++
      writing new private key to 'private/cakey.pem'
      Enter PEM pass phrase:
      Verifying - Enter PEM pass phrase:
      -----
      You are about to be asked to enter information that will be incorporated
      into your certificate request.
      What you are about to enter is what is called a Distinguished Name or a DN.
      There are quite a few fields but you can leave some blank
      For some fields there will be a default value,
      If you enter '.', the field will be left blank.
      -----
      Country Name (2 letter code) []:US
      State or Province Name (full name) []:California
      Locality Name (eg, city) []:Menlo Park
      Organization Name (eg, company) [Unconfigured OpenSSL Installation]:Oracle
      Organizational Unit Name (eg, section) []:Solaris
      Common Name (eg, YOUR name) []:somehost.somedomain.example.com
      Email Address []:someuser@example.com
      req

      This command creates and processes certificate requests.

      –new

      This req option generates a new certificate request.

      –x509

      This req option creates a self-signed certificate.

      –keyout private/cakey.pem

      This req option enables you to assign private/cakey.pem as the file name for your newly created private key.

      –out cacert.pem

      This req option enables you to assign cacert.pem as your output file.

      –days 365

      This req option enables you to certify the certificate for 365 days. The default value is 30.

      –config openssl.cnf

      This req option enables you to specify openssl.cnf as the configuration file.

      Note that this command requires that you provide the following:

      • Country Name, such as US.

      • State or Province Name, such as California.

      • Locality Name, such as Menlo Park.

      • Organization Name, such as Oracle.

      • Organizational Unit Name, such as Solaris.

      • Common Name, which is the machine's fully qualified host name. For more information, see the check-hostname(1M) man page.

      • Email Address, such as someuser@example.com.

  4. (Optional)If you need a new secure connection, make a new certificate and sign the new certificate with the certificate authority.
    1. Make a new certificate.
      # cd /etc/mail/certs/CA
      # openssl req -nodes -new -x509 -keyout newreq.pem -out newreq.pem -days 365 \
      -config openssl.cnf
      Generating a 1024 bit RSA private key
      ..............++++++
      ..............++++++
      writing new private key to 'newreq.pem'
      -----
      You are about to be asked to enter information that will be incorporated
      into your certificate request.
      What you are about to enter is what is called a Distinguished Name or a DN.
      There are quite a few fields but you can leave some blank
      For some fields there will be a default value,
      If you enter '.', the field will be left blank.
      -----
      Country Name (2 letter code) []:US
      State or Province Name (full name) []:California
      Locality Name (eg, city) []:Menlo Park
      Organization Name (eg, company) [Unconfigured OpenSSL Installation]:Oracle
      Organizational Unit Name (eg, section) []:Solaris
      Common Name (eg, YOUR name) []:somehost.somedomain.example.com
      Email Address []:someuser@example.com

      This command requires that you provide the same information that you provided in step 3c.

      Note that in this example, the certificate and private key are in the file newreq.pem.

    2. Sign the new certificate with the certificate authority.
      # cd /etc/mail/certs/CA
      # openssl x509 -x509toreq -in newreq.pem -signkey newreq.pem -out tmp.pem
      Getting request Private Key
      Generating certificate request
      # openssl ca -config openssl.cnf -policy policy_anything -out newcert.pem -infiles tmp.pem
      Using configuration from openssl.cnf
      Enter pass phrase for /etc/mail/certs/CA/private/cakey.pem:
      Check that the request matches the signature
      Signature ok
      Certificate Details:
              Serial Number: 1 (0x1)
              Validity
                  Not Before: Jun 23 18:44:38 2005 GMT
                  Not After : Jun 23 18:44:38 2006 GMT
              Subject:
                  countryName               = US
                  stateOrProvinceName       = California
                  localityName              = Menlo Park
                  organizationName          = Oracle
                  organizationalUnitName    = Solaris
                  commonName                = somehost.somedomain.example.com
                  emailAddress              = someuser@example.com
              X509v3 extensions:
                  X509v3 Basic Constraints: 
                      CA:FALSE
                  Netscape Comment: 
                      OpenSSL Generated Certificate
                  X509v3 Subject Key Identifier: 
                      93:D4:1F:C3:36:50:C5:97:D7:5E:01:E4:E3:4B:5D:0B:1F:96:9C:E2
                  X509v3 Authority Key Identifier: 
                      keyid:99:47:F7:17:CF:52:2A:74:A2:C0:13:38:20:6B:F1:B3:89:84:CC:68
                      DirName:/C=US/ST=California/L=Menlo Park/O=Oracle/OU=Solaris/\
                      CN=someuser@example.com/emailAddress=someuser@example.com
                      serial:00
      
      Certificate is to be certified until Jun 23 18:44:38 2006 GMT (365 days)
      Sign the certificate? [y/n]:y
      
      
      1 out of 1 certificate requests certified, commit? [y/n]y
      Write out database with 1 new entries
      Data Base Updated
      # rm -f tmp.pem

      In this example the file newreq.pem contains the unsigned certificate and private key. The file newcert.pem contains the signed certificate.

      x509 utility

      Displays certificate information, converts certificates to various forms, and signs certificate requests

      ca application

      Used to sign certificate requests in a variety of forms and to generate CRLs (certificate revocation lists)

  5. Enable sendmail to use the certificates by adding the following lines to your .mc file.
    define(`confCACERT_PATH', `/etc/mail/certs')dnl
    define(`confCACERT', `/etc/mail/certs/CAcert.pem')dnl
    define(`confSERVER_CERT', `/etc/mail/certs/MYcert.pem')dnl
    define(`confSERVER_KEY', `/etc/mail/certs/MYkey.pem')dnl
    define(`confCLIENT_CERT', `/etc/mail/certs/MYcert.pem')dnl
    define(`confCLIENT_KEY', `/etc/mail/certs/MYkey.pem')dnl

    For more information, see Configuration File Options for Running SMTP With TLS.

  6. Rebuild and install your sendmail.cf file in your /etc/mail directory.

    For detailed instructions, see Changing the sendmail Configuration.

  7. Create symbolic links from the files you created with openssl to the files you defined in your .mc file.
    # cd /etc/mail/certs
    # ln -s CA/cacert.pem CAcert.pem
    # ln -s CA/newcert.pem MYcert.pem
    # ln -s CA/newreq.pem MYkey.pem
  8. For added security, deny read permission to group and others for MYkey.pem.
    # chmod go-r MYkey.pem
  9. Use a symbolic link to install CA certs in the directory assigned to confCACERT_PATH.
    # C=CAcert.pem
    # ln -s $C `openssl x509 -noout -hash < $C`.0
  10. For secure mail with other hosts, install their host certificates.
    1. Copy the file defined by the other host's confCACERT option to /etc/mail/certs/host.domain.cert.pem.

      Replace host.domain with the other host's fully qualified host name.

    2. Use a symbolic link to install CA certs in the directory assigned to confCACERT_PATH.
      # C=host.domain.cert.pem
      # ln -s $C `openssl x509 -noout -hash < $C`.0

      Replace host.domain with the other host's fully qualified host name.

  11. Restart sendmail.
    # svcadm enable network/smtp:sendmail

Example 2-2  Received: Mail Header

The following is an example of a Received: header for secure mail with TLS.

Received: from his.example.com ([IPv6:2001:db8:3c4d:15::1a2f:1a2b])
        by her.example.com (8.13.4+Sun/8.13.4) with ESMTP id j2TNUB8i242496
        (version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-SHA bits=256 verify=OK)
        for <janepc@her.example.com>; Tue, 29 Mar 2005 15:30:11 -0800 (PST)
Received: from her.example.com (her.city.example.com [192.168.0.0])
        by his.example.com (8.13.4+Sun/8.13.4) with ESMTP id j2TNU7cl571102
        version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-SHA bits=256 verify=OK)
        for <janepc@her.example.com>; Tue, 29 Mar 2005 15:30:07 -0800 (PST)

Note that the value for verify is OK, which means that the authentication was successful. For more information, see Macros for Running SMTP With TLS.

Read This Pages :
http://hackage.haskell.org/package/HaskellNet-SSL-0.2.1/docs/Network-HaskellNet-SMTP-SSL.html
Easily Connector :) https://github.com/dpwright/HaskellNet-SSL
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