Application Inspection and Control for SMTP

The Application Inspection for SMTP feature provides an intense provisioning mechanism that can be configured to inspect packets on a granular level so that malicious network activity, related to the transfer of e-mail at the application level, can be identified and controlled. This feature qualifies the Cisco IOS firewall extended Simple Mail Transfer Protocol (ESMTP) module as an “SMTP application firewall,” which protects in a similar way to that of an HTTP application firewall.

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Prerequisites for Application Inspection and Control for SMTP

Follow the appropriate configuration tasks outlined in the Zone-Based Policy Firewall module before configuring the Application Inspection and Control for SMTP feature. This module contains important information about class-maps and policy-maps and their associated “match” statements necessary for configuring an SMTP policy.

SMTP Policy Requirements

Both SMTP and ESMTP inspection provide a basic method for exchanging e-mail messages between the client and server to negotiate capabilities and use these capabilities in an e-mail transaction. An ESMTP session is similar to an SMTP session, except for one difference--the Extended HELO (EHLO) command. The EHLO command is sent by a client to initiate the capability dialogue. After the client receives a successful response to the EHLO command, the client works the same way as SMTP, except that the client may issue new extended commands, and it may add a few parameters to the MAIL FROM and REPT TO commands.

Previously, if the Cisco IOS software was configured to inspect SMTP session only, inspection was configured by entering the match protocol smtp command. This action would “mask” the EHLO command to prevent capability negotiation and cause the client to go back to the HELO command and basic SMTP.

To have a workable policy for both ESMTP and SMTP inspection, the match protocol smtp command must be configured in the top-level policy before the Application Inspection and Control for SMTP features are implemented. See the Configuring a Default Policy for Application Inspection task for more information.

The SMTP policy (which specifies the particular SMTP configuration) is included as a child-policy in the top-level “inspect” policy-map. See the “Top-level Class Maps and Policy Maps” section in the Zone-Based Policy Firewall module for more information.

Restrictions for Application Inspection and Control for SMTP

The Application Inspection and Control for SMTP feature has the following restrictions:

  • The match cmd-line length gt command filter can co-exist only with a match cmd verb command filter in the SMTP match-all class -map (class-map type inspect smtp). Any attempt to pair the match cmd-line length gt command filter with any other filter is not allowed by the CLI.

  • The alternative data transfer SMTP command extension BDAT is not supported. This command is substituted for the DATA command while the SMTP body is transferred. The BDAT command extension is used by the Cisco IOS firewall to mask the CHUNKING keyword in the EHLO response to the Application Inspection and Control for SMTP feature, preventing a client from using it.

  • The “mask” action can be configured only with a class having either or both of the match cmd verb or match ehlo reply commands. This action cannot be configured with a class having any other filter.

Information About Application Inspection and Control for SMTP

The Application Inspection and Control for SMTP feature inspects SMTP in a granular way and is complemented by an intensive provisioning system to help filter e-mail.

Benefits of Application Inspection and Control for SMTP

The Application Inspection and Control for SMTP feature provides the following benefits:

  • E-mail senders and user accounts are restricted to filter spam e-mail from suspected domains.

  • An action can be specified, which occurs when a number of invalid recipients appears on an SMTP connection. This action helps identify spammers who are looking for valid user accounts.

  • The number of invalid SMTP recipients can be restricted by specifying a maximum number for invalid recipients on an SMTP connection.

  • A pattern can be specified that identifies e-mail addressed to a particular recipient or domain in cases where a server is functioning as a relay.

  • A provisioning mechanism that provides masks specified verbs in an SMTP connection to block potentially dangerous SMTP commands.

  • The maximum length value for the SMTP e-mail header can be specified to prevent a Denial of Service (DoS) attack (also called a buffer overflow attack). A DoS attack occurs when the attacker continuously sends a large number of incomplete IP fragments, causing the firewall to lose time and memory while trying to reassemble the fake packets.

  • The maximum length of an SMTP command line can be specified to prevent a DoS attack.

  • Multipurpose Internet Mail Extension (MIME) content file-types (text, HTML, images, applications, documents,and so on) can be restricted in the body of the e-mail from being transmitted over SMTP.

  • Unknown content-encoding types can be restricted from being transmitted over SMTP.

  • Specified content-types and content encoding types can be restricted in the SMTP e-mail body.

  • Monitor arbitrary patterns (text strings) in the SMTP e-mail message header (subject field) or body.

  • A parameter in an EHLO server reply and mask can be specified to prevent a sender (client) from using the service extension in the server reply.

  • An SMTP connection can be dropped with an SMTP sender (client) if the SMTP connection violates the specified policy.

  • SMTP commands or the parameters returned by the server in response to an EHLO command can be explicitly masked by specifying these SMTP commands.

  • An action can be logged for a class type in an SMTP policy-map.

Cisco Common Classification Policy Language

The Cisco Common Classification Policy Language (C3PL) CLI structure is used to provision ESMTP inspection. ESMTP is provisioned by defining a match criterion on an SMTP class-map and associate actions to the match criterion defined in the SMTP policy-map. The Application Inspection and Control for SMTP feature adds new match criteria and actions to the existing SMTP policy maps that are discussed in the Zone-Based Policy Firewall module, which describes the Cisco IOS unidirectional firewall policy between groups of interfaces known as zones.

Figure 1. ESMTP Communication Between a Sender and Receiver

Common Classification Engine SMTP Database and Action Module

The Common Classification Engine (CCE) SMTP database is the site at which manually configured policy information is processed and converted into signatures. The information in these signatures is put into regular expression tables, which are then used to parse packets as they are switched by a router.

The SMTP database has two interfaces. One interface has the control plane, which is used to accept user configured policies, and the other interface has the CCE data-plane engine, which is used to classify a packet.

An action module is used as a part of the Context-Based Access Control (CBAC) SMTP inspection module to organize and trigger SMTP inspection. CBAC is used to detect and block SMTP attacks (illegal SMTP commands) and sends notifications when SMTP attacks occur.

How to Configure Application Inspection and Control for SMTP

Configuring a Default Policy for Application Inspection

If no policy is configured for SMTP, then there is no application inspection for SMTP. The firewall creates a TCP session and only performs “pinholing,” which allows an application to have access to the protected network. Having an open gap in a firewall can expose the protected system to malicious abuse. The steps below are used to provide minimum application inspection protections for SMTP by enforcing the EHLO and HELO SMTP commands.

SUMMARY STEPS

    1.    enable

    2.    configure terminal

    3.    class-map type inspect smtp class-map-name

    4.    match protocol smtp


DETAILED STEPS
     Command or ActionPurpose
    Step 1 enable


    Example:
    Router> enable
     

    Enables privileged EXEC mode.

    • Enter your password if prompted.

     
    Step 2 configure terminal


    Example:
    Router# configure terminal
     

    Enters global configuration mode.

     
    Step 3 class-map type inspect smtp class-map-name


    Example:
    Router(config)# class-map type inspect smtp c1
     

    Creates a class map for the SMTP protocol and enters class-map configuration mode.

     
    Step 4 match protocol smtp


    Example:
    Router(config-cmap)# match protocol smtp
     

    Enables inspection for ESMTP and SMTP.

     

    Restricting Spam from a Suspicious E-Mail Sender Address or Domain

    An e-mail sender and user accounts can be restricted to filter spam e-mail from suspected domains. Spam is restricted by using the match sender address regex command to match the parameter-map name of a specific traffic pattern that specifies a sender domain or e-mail address in the SMTP traffic. The specified pattern is scanned in the parameter for the SMTP MAIL FROM: command.

    SUMMARY STEPS

      1.    enable

      2.    configure terminal

      3.    parameter-map type regex parameter-map-name

      4.    pattern traffic-pattern

      5.    exit

      6.    class-map type inspect smtp match-any class-map-name

      7.    match sender address regex parameter-map-name

      8.    exit

      9.    policy-map type inspect smtp policy-map-name

      10.    class type inspect smtp class-map-name

      11.    log

      12.    reset


    DETAILED STEPS
       Command or ActionPurpose
      Step 1 enable


      Example:
      Router> enable
       

      Enables privileged EXEC mode.

      • Enter your password if prompted.

       
      Step 2 configure terminal


      Example:
      Router# configure terminal
       

      Enters global configuration mode.

       
      Step 3 parameter-map type regex parameter-map-name


      Example:
      Router(config)# parameter-map type regex bad-guys
       

      Enter the parameter-map name of a specific traffic pattern. Once the parameter-map name is specified, parameter-map profile configuration mode is entered.

       
      Step 4 pattern traffic-pattern


      Example:
      Router(config-profile)# pattern “*deals\.com”


      Example:
      Router(config-profile)# pattern “*crazyperson*@wrdmail\.com”
       

      Specifies the Cisco IOS regular expression (regex) pattern that matches the traffic pattern for the e-mail sender or user accounts from suspected domains that are causing the spam e-mail.

       
      Step 5 exit 

      Exits parameter-map profile configuration mode.

       
      Step 6 class-map type inspect smtp match-any class-map-name


      Example:
      Router(config)# class-map type inspect smtp match-any c1
       

      Creates a class map for the SMTP protocol so the match criteria is set to match any criteria for this class map and enters class-map configuration mode.

       
      Step 7 match sender address regex parameter-map-name


      Example:
      Router(config-cmap)# match sender address regex bad-guys
       

      Enters the parameter-map name class, which was defined in Step 3, to specify the Cisco IOS regular expression (regex) patterns for the class-map.

       
      Step 8 exit 

      Exits class-map configuration mode.

       
      Step 9 policy-map type inspect smtp policy-map-name


      Example:
      Router(config)# policy-map type inspect smtp p1
       

      Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

       
      Step 10 class type inspect smtp class-map-name


      Example:
      Router(config-pmap)# class type inspect smtp c1
       

      Configures SMTP inspection parameters for this class map.

       
      Step 11 log


      Example:
      Router(config-pmap)# log
       

      Logs an action related to this class-type in the SMTP policy map.

       
      Step 12 reset


      Example:
      Router(config-pmap)# reset
       

      (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

       

      Identifying and Restricting Spammers Searching for User Accounts in a Domain

      Spammers who search for a large number of user accounts in a domain typically send the same e-mail to all the user accounts they find in this domain. Spammers can be identified and restricted from searching for user accounts in a domain by using the match recipient count gt command to specify an action that occurs when a number of invalid recipients appear on an SMTP connection.


      Note


      The match recipient count gt command does not count the number of recipients specified in the To or Cc fields in the e-mail header.


      SUMMARY STEPS

        1.    enable

        2.    configure terminal

        3.    class-map type inspect smtp class-map-name

        4.    match recipient count gt value

        5.    exit

        6.    policy-map type inspect smtp policy-map-name

        7.    class type inspect smtp class-map-name

        8.    reset


      DETAILED STEPS
         Command or ActionPurpose
        Step 1 enable


        Example:
        Router> enable
         

        Enables privileged EXEC mode.

        • Enter your password if prompted.

         
        Step 2 configure terminal


        Example:
        Router# configure terminal
         

        Enters global configuration mode.

         
        Step 3 class-map type inspect smtp class-map-name


        Example:
        Router(config)# class-map type inspect smtp c1
         

        Creates a class map for the SMTP protocol and enters class-map configuration mode.

         
        Step 4 match recipient count gt value


        Example:
        Router(config-cmap)# match recipient count gt 25
         

        Sets a limit on the number of RCPT SMTP commands sent by the sender (client) to recipients who are specified in a single SMTP transaction.

        This command determines the number of RCPT lines and invalid recipients (for which the server has replied “500 No such address”) in the SMTP transaction.

         
        Step 5 exit 

        Exits class-map configuration mode.

         
        Step 6 policy-map type inspect smtp policy-map-name


        Example:
        Router(config)# policy-map type inspect smtp p1
         

        Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

        • The policy-map-name argument is the name of the policy map.

         
        Step 7 class type inspect smtp class-map-name


        Example:
        Router(config-pmap)# class type inspect smtp c1
         

        Configures SMTP inspection parameters for this class map.

         
        Step 8 reset


        Example:
        Router(config-pmap)# reset
         

        (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

         

        Restricting the Number of Invalid SMTP Recipients

        If a sender specifies in an invalid e-mail recipient and SMTP encounters this invalid recipient on the SMTP connection, then SMTP sends an error code reply to the e-mail sender (client) to specify another recipient. In this case, the event did not violate the SMTP protocol or indicate that this particular SMTP connection is bad. However, if a pattern of invalid recipients appears, then a reasonable threshold can be set to restrict these nuisance SMTP connections. The match recipient invalid count gt command is used to help identify and restrict the number of invalid SMTP recipients that can appear in an e-mail from senders who try common names on a domain in the hope that they discover a valid username to whom they can send spam.

        SUMMARY STEPS

          1.    enable

          2.    configure terminal

          3.    class-map type inspect smtp class-map-name

          4.    match recipient invalid count gt value

          5.    exit

          6.    policy-map type inspect smtp policy-map-name

          7.    class type inspect smtp class-map-name

          8.    reset


        DETAILED STEPS
           Command or ActionPurpose
          Step 1 enable


          Example:
          Router> enable
           

          Enables privileged EXEC mode.

          • Enter your password if prompted.

           
          Step 2 configure terminal


          Example:
          Router# configure terminal
           

          Enters global configuration mode.

           
          Step 3 class-map type inspect smtp class-map-name


          Example:
          Router(config)# class-map type inspect smtp c1
           

          Creates a class map for the SMTP protocol and enters class-map configuration mode.

           
          Step 4 match recipient invalid count gt value


          Example:
          Router(config-cmap)# match recipient invalid count gt 5 
           

          Specifies a maximum number of invalid e-mail recipients on this SMTP connection.

           
          Step 5 exit 

          Exits class-map configuration mode.

           
          Step 6 policy-map type inspect smtp policy-map-name


          Example:
          Router(config)# policy-map type inspect smtp p1
           

          Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

           
          Step 7 class type inspect smtp class-map-name


          Example:
          Router(config-pmap)# class type inspect smtp c1
           

          Configures SMTP inspection parameters for this class map.

           
          Step 8 reset


          Example:
          Router(config-pmap)# reset
           

          (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

           

          Specifying a Recipient Pattern to Learn Spam Senders and Domain Information

          A nonexistent e-mail recipient pattern can be specified to learn about spam senders and their domain information by luring them to use this nonexistent e-mail recipient pattern. This pattern is a regular-expression (regex) that can be specified to identify an e-mail addressed to a particular recipient or domain when a server is functioning as a relay. The specified pattern is checked in the SMTP RCPT command (SMTP envelope) parameter to identify if the recipient is either used as an argument or a source-list to forward mail in the route specified in the list.


          Note


          The match recipient address regex command does not operate on the To or Cc fields in the e-mail header.


          SUMMARY STEPS

            1.    enable

            2.    configure terminal

            3.    parameter-map type regex parameter-map-name

            4.    pattern traffic-pattern

            5.    exit

            6.    class-map type inspect smtp class-map-name

            7.    match recipient address regex parameter-map-name

            8.    exit

            9.    policy-map type inspect smtp policy-map-name

            10.    class type inspect smtp class-map-name

            11.    log

            12.    reset


          DETAILED STEPS
             Command or ActionPurpose
            Step 1 enable


            Example:
            Router> enable
             

            Enables privileged EXEC mode.

            • Enter your password if prompted.

             
            Step 2 configure terminal


            Example:
            Router# configure terminal
             

            Enters global configuration mode.

             
            Step 3 parameter-map type regex parameter-map-name


            Example:
            Router(config)# parameter-map type regex known-unknown-users
             

            Enter the parameter-map name of a specific traffic pattern. Once the parameter-map name is specified, parameter-map profile configuration mode is entered.

             
            Step 4 pattern traffic-pattern


            Example:
            Router(config-profile)# pattern “username@mydomain.com”
             

            Specifies a Cisco IOS regular expression (regex) pattern that matches the traffic pattern for the e-mail sender or user accounts from suspected domains that are causing the spam e-mail. In the example, “username” is configured as the name for a fake e-mail account used to discover senders (and their domain) when they try to send spam e-mail to this fake account.

             
            Step 5 exit 

            Exits parameter-map profile configuration mode.

             
            Step 6 class-map type inspect smtp class-map-name


            Example:
            Router(config)# class-map type inspect smtp c1
             

            Creates a class map for the SMTP protocol and enters class-map configuration mode.

             
            Step 7 match recipient address regex parameter-map-name


            Example:
            Router(config-cmap)# match recipient address regex known-unknown-users
             

            Specifies the nonexistent e-mail recipient pattern in order to learn spam senders and their domain information by luring them to use this contrived e-mail recipient.

             
            Step 8 exit 

            Exits class-map configuration mode.

             
            Step 9 policy-map type inspect smtp policy-map-name


            Example:
            Router(config)# policy-map type inspect smtp p1
             

            Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

             
            Step 10 class type inspect smtp class-map-name


            Example:
            Router(config-pmap)# class type inspect smtp c1
             

            Configures SMTP inspection parameters for this class map.

             
            Step 11 log


            Example:
            Router(config-pmap)# log
             

            Logs an action related to this class-type in the SMTP policy map.

             
            Step 12 reset


            Example:
            Router(config-pmap)# reset
             

            (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

             

            Hiding Specified Private SMTP Commands on an SMTP Connection

            Use this task to hide or “mask” commonly encountered SMTP verbs (SMTP commands) or specified private SMTP verbs used to provision an SMTP connection.

            Specified verbs, such as the ATRN, ETRN, BDAT verbs may be considered vulnerable to exploitation if seen by a sender (client). The most commonly encountered SMTP verbs are listed along with the facility to specify a private verb as a string (using the WORD option).


            Note


            The BDAT verb (used as an alternative to DATA) is not used, so in its place, the CHUNKING keyword is masked in the EHLO response. However, if the sender (client) continues to send the BDAT command, it is masked.



            Note


            Using the mask command applies to certain match command filters like match cmd verb. Validations are performed to make this check and the configuration is not be accepted in case of invalid combinations.


            SUMMARY STEPS

              1.    enable

              2.    configure terminal

              3.    class-map type inspect smtp class-map-name

              4.    match cmd verb {verb-name | WORD}

              5.    exit

              6.    policy-map type inspect smtp policy-map-name

              7.    class type inspect smtp class-map-name

              8.    mask


            DETAILED STEPS
               Command or ActionPurpose
              Step 1 enable


              Example:
              Router> enable
               

              Enables privileged EXEC mode.

              • Enter your password if prompted.

               
              Step 2 configure terminal


              Example:
              Router# configure terminal
               

              Enters global configuration mode.

               
              Step 3 class-map type inspect smtp class-map-name


              Example:
              Router(config)# class-map type inspect smtp c1
               

              Creates a class map for the SMTP protocol and enters class-map configuration mode.

               
              Step 4 match cmd verb {verb-name | WORD}


              Example:
              Router(config-cmap)# match cmd verb ATRN
               

              Specifies either the private verb name to “mask” that is used to provision an SMTP connection.

              • The verb-name argument is the name of an SNMP command verb.

              • The WORD argument is the name of a user-specified SMTP command verb, which is treated as an unknown verb and is masked regardless of whether the ‘mask action is configured for the class or not.

               
              Step 5 exit 

              Exits class-map configuration mode.

               
              Step 6 policy-map type inspect smtp policy-map-name


              Example:
              Router(config)# policy-map type inspect smtp p1
               

              Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

               
              Step 7 class type inspect smtp class-map-name


              Example:
              Router(config-pmap)# class type inspect smtp c1
               

              Configures SMTP inspection parameters for this class map.

               
              Step 8 mask


              Example:
              Router(config-pmap)# mask
               

              Explicitly masks the specified SMTP commands or the parameters returned by the server in response to an EHLO command.

               

              Preventing a DoS Attack by Limiting the Length of the SMTP Header

              A DoS attack (also called a buffer overflow attack) by a malicious sender (client) can cause the SMTP application firewall to lose time and memory while trying to reassemble the fake packets (large e-mail headers) associated with the e-mail. In an SMTP transaction, the header portion of an e-mail is considered part of the DATA area, which contains fields like Subject, From, To, Cc, Date, and proprietary information, which is used by a recipient’s e-mail agent to process the e-mail. A DoS attack can be prevented by using the match header length gt command to limit the length of the SMTP header that can be received. If a match is found, possible actions that can be specified within the policy are as follows: allow, reset, or log (the log action triggers a syslog message when a match is found).

              SUMMARY STEPS

                1.    enable

                2.    configure terminal

                3.    class-map type inspect smtp class-map-name

                4.    match header length gt bytes

                5.    exit

                6.    policy-map type inspect smtp policy-map-name

                7.    class type inspect smtp class-map-name

                8.    reset


              DETAILED STEPS
                 Command or ActionPurpose
                Step 1 enable


                Example:
                Router> enable
                 

                Enables privileged EXEC mode.

                • Enter your password if prompted.

                 
                Step 2 configure terminal


                Example:
                Router# configure terminal
                 

                Enters global configuration mode.

                 
                Step 3 class-map type inspect smtp class-map-name


                Example:
                Router(config)# class-map type inspect smtp c1
                 

                Creates a class map for the SMTP protocol and enters class-map configuration mode.

                 
                Step 4 match header length gt bytes


                Example:
                Router(config-cmap)# match header length gt 16000
                 

                Specifies a value from 1 to 65535 that limits the maximum length of the SMTP header in bytes to thwart DoS attacks.

                 
                Step 5 exit 

                Exits class-map configuration mode.

                 
                Step 6 policy-map type inspect smtp policy-map-name


                Example:
                Router(config)# policy-map type inspect smtp p1
                 

                Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                 
                Step 7 class type inspect smtp class-map-name


                Example:
                Router(config-pmap)# class type inspect smtp c1
                 

                Configures SMTP inspection parameters for this class map.

                 
                Step 8 reset


                Example:
                Router(config-pmap)# reset
                 

                (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

                 

                Preventing a DoS Attack by Limiting the Length or TYPE of SMTP Command Line

                The following task is used to limit the length of an SMTP command line to prevent a DoS attack, which occurs when a malicious sender (client) specifies large command lines in an e-mail to perform DoS attacks on SMTP servers.

                SUMMARY STEPS

                  1.    enable

                  2.    configure terminal

                  3.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                  4.    match cmd {line length gt length | verb {AUTH | DATA | EHLO | ETRN | EXPN | HELO | HELP | MAIL NOOP | QUIT | RCPT | RSET | SAML | SEND | SOML | STARTTLS | VERB | VRFY | WORD}}

                  5.    exit

                  6.    policy-map type inspect smtp policy-map-name

                  7.    class type inspect smtp class-map-name

                  8.    reset


                DETAILED STEPS
                   Command or ActionPurpose
                  Step 1 enable


                  Example:
                  Router> enable
                   

                  Enables privileged EXEC mode.

                  • Enter your password if prompted.

                   
                  Step 2 configure terminal


                  Example:
                  Router# configure terminal
                   

                  Enters global configuration mode.

                   
                  Step 3 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                  Example:
                  Router(config)# class-map type inspect smtp c1
                   

                  Enters class-map configuration mode and creates a class map for the SMTP protocol.

                  • The class-map-name argument by itself specifies a single class-map.

                  • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                  • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                  Note   

                  If no match cmd verb command statement is specified in a class-map type inspect smtp match-all command statement for a class-map, which contains the match cmd line length gt command statement, then the class-map applies to all SMTP commands.

                   
                  Step 4 match cmd {line length gt length | verb {AUTH | DATA | EHLO | ETRN | EXPN | HELO | HELP | MAIL NOOP | QUIT | RCPT | RSET | SAML | SEND | SOML | STARTTLS | VERB | VRFY | WORD}}


                  Example:
                  Router(config-cmap)# match header length gt 16000
                   

                  Specifies a value that limits the length of the ESMTP command line or ESMTP command line verb used to thwart DoS attacks.

                  • The length argument specifies the ESMTP command line greater than the length of a number of characters from 1 to 65535.

                   
                  Step 5 exit  

                  Exits class-map configuration mode.

                   
                  Step 6 policy-map type inspect smtp policy-map-name


                  Example:
                  Router(config)# policy-map type inspect smtp p1
                   

                  Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                   
                  Step 7 class type inspect smtp class-map-name


                  Example:
                  Router(config-pmap)# class type inspect smtp c1
                   

                  Configures an SMTP class-map firewall for SMTP inspection parameters.

                   
                  Step 8 reset


                  Example:
                  Router(config-pmap)# reset
                   

                  (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

                   

                  Examples

                  The following configuration has class-map c2 match when the length of the e-mail (MAIL) command exceeds 256 bytes.

                  When the class-map type inspect smtp match-all command statement is configured with the match cmd verb command statement, only the match cmd line length gt command statement can coexist.

                  class-map type inspect smtp match-all c2
                    match cmd line length gt 256
                    match cmd verb MAIL
                  

                  There are no match restrictions in case of a class-map type inspect smtp match-any command statement for a class map because the class-map applies to all SMTP commands.

                  Restricting Content File Types in the Body of the E-Mail

                  The match mime content-type regex command is used to specify MIME content file types, which are restricted in attachments in the body of the e-mail being sent over SMTP. See the Example: MIME E-Mail Format section for more information.

                  SUMMARY STEPS

                    1.    enable

                    2.    configure terminal

                    3.    parameter-map type regex parameter-map-name

                    4.    pattern traffic-pattern

                    5.    exit

                    6.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                    7.    match mime content-type regex content-type-regex

                    8.    exit

                    9.    policy-map type inspect smtp policy-map-name

                    10.    class type inspect smtp class-map-name

                    11.    log


                  DETAILED STEPS
                     Command or ActionPurpose
                    Step 1 enable


                    Example:
                    Router> enable
                     

                    Enables privileged EXEC mode.

                    • Enter your password if prompted.

                     
                    Step 2 configure terminal


                    Example:
                    Router# configure terminal
                     

                    Enters global configuration mode.

                     
                    Step 3 parameter-map type regex parameter-map-name


                    Example:
                    Router(config)# parameter-map type regex jpeg
                     

                    Enter the parameter-map name of a specific traffic pattern. Once the parameter-map name is specified, parameter-map profile configuration mode is entered.

                     
                    Step 4 pattern traffic-pattern


                    Example:
                    Router(config-profile)# pattern “*image//*”
                     

                    Specifies a Cisco IOS regular expression (regex) pattern that matches the traffic pattern for the e-mail sender or user accounts from suspected domains that are causing the spam e-mail.

                     
                    Step 5 exit  

                    Exits parameter-map profile configuration mode.

                     
                    Step 6 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                    Example:
                    Router(config)# class-map type inspect smtp c1
                     

                    Enters class-map configuration mode and creates a class map for the SMTP protocol.

                    • The class-map-name argument by itself specifies a single class-map.

                    • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                    • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                     
                    Step 7 match mime content-type regex content-type-regex


                    Example:
                    Router(config-cmap)# match mime content-type regex jpeg
                     

                    Specifies the MIME content file type, which are restricted in attachments in the body of the e-mail being sent over SMTP.

                    • The content-type-regex argument is the type of content in the MIME header in regular expression form.

                    This example lets the user specify any form of JPEG image content to be restricted.

                    Note   

                    The actual content of the MIME part is not checked to see if it matches with the declared content-type in the MIME header.

                     
                    Step 8 exit  

                    Exits class-map configuration mode.

                     
                    Step 9 policy-map type inspect smtp policy-map-name


                    Example:
                    Router(config)# policy-map type inspect smtp p1
                     

                    Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                     
                    Step 10 class type inspect smtp class-map-name


                    Example:
                    Router(config-pmap)# class type inspect smtp c1
                     

                    Configures an SMTP class-map firewall for SMTP inspection parameters.

                     
                    Step 11 log


                    Example:
                    Router(config-pmap)# log
                     

                    Logs an action related to this class-type in the SMTP policy map.

                     

                    Restricting Unknown Content Encoding Types from Being Transmitted

                    Unknown MIME content-encoding types or values can be restricted from being transmitted over SMTP by using one of the following parameters with the match mime encodingcommand.

                    These preconfigured content-transfer-encoding types act as a filter on the content-transfer-encoding field in the MIME header within the SMTP body. The uuencode encoding type is not recognized as a standard type by the MIME RFCs because many subtle differences exist in its various implementations. However, since it is used by some mail systems, the x-uuencode type is included in the preconfigured list.

                    SUMMARY STEPS

                      1.    enable

                      2.    configure terminal

                      3.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                      4.    match mime encoding {unknown | WORD | encoding-type}

                      5.    exit

                      6.    policy-map type inspect smtp policy-map-name

                      7.    class type inspect smtp class-map-name

                      8.    log


                    DETAILED STEPS
                       Command or ActionPurpose
                      Step 1 enable


                      Example:
                      Router> enable
                       

                      Enables privileged EXEC mode.

                      • Enter your password if prompted.

                       
                      Step 2 configure terminal


                      Example:
                      Router# configure terminal
                       

                      Enters global configuration mode.

                       
                      Step 3 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                      Example:
                      Router(config)# class-map type inspect smtp c1
                       

                      Enters class-map configuration mode and creates a class map for the SMTP protocol.

                      • The class-map-name argument by itself specifies a single class-map.

                      • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                      • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                       
                      Step 4 match mime encoding {unknown | WORD | encoding-type}


                      Example:
                      Router (config-cmap)# match mime encoding quoted-printable
                       

                      Restricts unknown MIME content-encoding types or values.

                      • The unknown keyword is used if content-transfer-encoding value in the e-mail does not match any of the ones in the list to restrict unknown and potentially dangerous encodings.

                      • The WORD argument is a user-defined content-transfer encoding type, which must begin with “X-” (for example, “X-myencoding-scheme”).

                      • The encoding-type argument specifies one of the following preconfigured content-transfer-encoding types:
                        • 7-bit-ASCII characters
                        • 8-bit-Facilitates the exchange of e-mail messages containing octets outside the 7-bit ASCII range.
                        • base64-Any similar encoding scheme that encodes binary data by treating it numerically and translating it into a base 64 representation.
                        • quoted-printable-Encoding using printable characters (that is alphanumeric and the equals sign "=") to transmit 8-bit data over a 7-bit data path. It is defined as a MIME content transfer encoding for use in Internet e-mail.
                        • binary-Representation for numbers using only two digits (usually, 0 and 1).
                        • x-uuencode-Nonstandard encoding.
                      Note   

                      The quoted-printable and base64 encoding types tell the e-mail client that a binary-to-text encoding scheme was used and that appropriate initial decoding is necessary before the message can be read with its original encoding.

                       
                      Step 5 exit 

                      Exits class-map configuration mode.

                       
                      Step 6 policy-map type inspect smtp policy-map-name


                      Example:
                      Router(config)# policy-map type inspect smtp p1
                       

                      Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                       
                      Step 7 class type inspect smtp class-map-name


                      Example:
                      Router(config-pmap)# class type inspect smtp c1
                       

                      Configures an SMTP class-map firewall for SMTP inspection parameters.

                       
                      Step 8 log


                      Example:
                      Router(config-pmap)# log
                       

                      Logs an action related to this class-type in the SMTP policy map.

                       

                      Specifying a Text String to Be Matched and Restricted in the Body of an E-Mail

                      The match body regex command can be used to specify an arbitrary text expression to restrict specified content-types and content encoding types for text and HTML in the body of the e-mail. The text or HTML pattern is scanned only if the encoding is 7-bit or 8-bit and the encoding is checked before attempting to match the pattern. If the pattern is of another encoding type (for example, base64, zip files, and so on), then the pattern cannot be scanned.


                      Note


                      Using this command can impact performance because the complete SMTP connection has to be scanned.


                      SUMMARY STEPS

                        1.    enable

                        2.    configure terminal

                        3.    parameter-map type regex parameter-map-name

                        4.    pattern traffic-pattern

                        5.    exit

                        6.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                        7.    match body regex parameter-map-name

                        8.    exit

                        9.    policy-map type inspect smtp policy-map-name

                        10.    class type inspect smtp class-map-name

                        11.    log


                      DETAILED STEPS
                         Command or ActionPurpose
                        Step 1 enable


                        Example:
                        Router> enable
                         

                        Enables privileged EXEC mode.

                        • Enter your password if prompted.

                         
                        Step 2 configure terminal


                        Example:
                        Router# configure terminal
                         

                        Enters global configuration mode.

                         
                        Step 3 parameter-map type regex parameter-map-name


                        Example:
                        Router(config)# parameter-map type regex doc-data
                         

                        Enter the parameter-map name of a specific traffic pattern. Once the parameter-map name is specified, parameter-map profile configuration mode is entered.

                         
                        Step 4 pattern traffic-pattern


                        Example:
                        Router(config-profile)# pattern “*UD-421590*”
                         

                        Specifies a Cisco IOS regular expression (regex) pattern that matches the traffic pattern for the e-mail sender or user accounts from suspected domains that are causing the spam e-mail.

                         
                        Step 5 exit 

                        Exits parameter-map profile configuration mode.

                         
                        Step 6 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                        Example:
                        Router(config)# class-map type inspect smtp c1
                         

                        Enters class-map configuration mode and creates a class map for the SMTP protocol.

                        • The class-map-name argument by itself specifies a single class-map.

                        • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                        • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                         
                        Step 7 match body regex parameter-map-name


                        Example:
                        Router(config-cmap)# match body regex doc-data
                         

                        Specifies an arbitrary text expression to restrict specified content-types and content encoding types for text and HTML in the “body” of the e-mail.

                         
                        Step 8 exit 

                        Exits class-map configuration mode.

                         
                        Step 9 policy-map type inspect smtp policy-map-name


                        Example:
                        Router(config)# policy-map type inspect smtp p1
                         

                        Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                         
                        Step 10 class type inspect smtp class-map-name


                        Example:
                        Router(config-pmap)# class type inspect smtp c1
                         

                        Configures an SMTP class-map firewall for SMTP inspection parameters.

                         
                        Step 11 log


                        Example:
                        Router(config-pmap)# log
                         

                        Logs an action related to this class-type in the SMTP policy map.

                         

                        Configuring the Monitoring of Text Patterns in an SMTP E-Mail Subject Field

                        The match header regex command can be used specify an arbitrary text expression in the SMTP e-mail message header (Subject field) or e-mail body such as Subject, Received, To, or other private header fields to monitor text patterns.

                        SUMMARY STEPS

                          1.    enable

                          2.    configure terminal

                          3.    parameter-map type regex parameter-map-name

                          4.    pattern traffic-pattern

                          5.    exit

                          6.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                          7.    match header regex parameter-map-name

                          8.    exit

                          9.    policy-map type inspect smtp policy-map-name

                          10.    class type inspect smtp class-map-name

                          11.    reset


                        DETAILED STEPS
                           Command or ActionPurpose
                          Step 1 enable


                          Example:
                          Router> enable
                           

                          Enables privileged EXEC mode.

                          • Enter your password if prompted.

                           
                          Step 2 configure terminal


                          Example:
                          Router# configure terminal
                           

                          Enters global configuration mode.

                           
                          Step 3 parameter-map type regex parameter-map-name


                          Example:
                          Router(config)# parameter-map type regex lottery-spam
                           

                          Enter the parameter-map name of a specific traffic pattern. Once the parameter-map name is specified, parameter-map profile configuration mode is entered.

                           
                          Step 4 pattern traffic-pattern


                          Example:
                          Router(config-profile)# pattern “Subject:*lottery*”
                           

                          Specifies a Cisco IOS regular expression (regex) pattern that matches the traffic pattern for the e-mail sender or user accounts from suspected domains that are causing the spam e-mail.

                           
                          Step 5 exit 

                          Exits parameter-map profile configuration mode.

                           
                          Step 6 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                          Example:
                          Router(config)# class-map type inspect smtp c1
                           

                          Enters class-map configuration mode and creates a class map for the SMTP protocol.

                          • The class-map-name argument by itself specifies a single class-map.

                          • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                          • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                           
                          Step 7 match header regex parameter-map-name


                          Example:
                          Router(config-cmap)# match header regex lottery-spam
                           

                          Specifies an arbitrary text expression in the SMTP e-mail message header to monitor text patterns.

                           
                          Step 8 exit 

                          Exits class-map configuration mode.

                           
                          Step 9 policy-map type inspect smtp policy-map-name


                          Example:
                          Router(config)# policy-map type inspect smtp p1
                           

                          Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                           
                          Step 10 class type inspect smtp class-map-name


                          Example:
                          Router(config-pmap)# class type inspect smtp c1
                           

                          Configures an SMTP class-map firewall for SMTP inspection parameters.

                           
                          Step 11 reset


                          Example:
                          Router(config-pmap)# reset
                           

                          (Optional) Drops an SMTP connection with an SMTP sender (client) if it violates the specified policy. This action sends an error code to the sender and closes the connection gracefully.

                           

                          Configuring a Parameter to Be Identified and Masked in the EHLO Server Reply

                          The match reply ehlo command is used to identify and mask a service extension parameter in the EHLO server reply (for example, 8BITMIME and ETRN) to prevent a sender (client) from using that particular service extension.

                          SUMMARY STEPS

                            1.    enable

                            2.    configure terminal

                            3.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                            4.    match reply ehlo {parameter | WORD}

                            5.    exit

                            6.    policy-map type inspect smtp policy-map-name

                            7.    class type inspect smtp class-map-name

                            8.    log

                            9.    mask


                          DETAILED STEPS
                             Command or ActionPurpose
                            Step 1 enable


                            Example:
                            Router> enable
                             

                            Enables privileged EXEC mode.

                            • Enter your password if prompted.

                             
                            Step 2 configure terminal


                            Example:
                            Router# configure terminal
                             

                            Enters global configuration mode.

                             
                            Step 3 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                            Example:
                            Router(config)# class-map type inspect smtp c1
                             

                            Enters class-map configuration mode and creates a class map for the SMTP protocol.

                            • The class-map-name argument by itself specifies a single class-map.

                            • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                            • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                             
                            Step 4 match reply ehlo {parameter | WORD}


                            Example:
                            Router(config-cmap)# match reply ehlo ETRN
                             

                            Identifies and masks a service extension parameter in the EHLO server reply.

                            • The parameter argument specifies a parameter from the well-known EHLO keywords.

                            • The WORD argument specifies an extension which is not on the EHLO list.

                             
                            Step 5 exit 

                            Exits class-map configuration mode.

                             
                            Step 6 policy-map type inspect smtp policy-map-name


                            Example:
                            Router(config)# policy-map type inspect smtp p1
                             

                            Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                             
                            Step 7 class type inspect smtp class-map-name


                            Example:
                            Router(config-pmap)# class type inspect smtp c1
                             

                            Configures an SMTP class-map firewall for SMTP inspection parameters.

                             
                            Step 8 log


                            Example:
                            Router(config-pmap)# log
                             

                            Logs an action related to this class-type in the SMTP policy map.

                             
                            Step 9 mask


                            Example:
                            Router(config-pmap)# mask
                             

                            Explicitly masks the specified SMTP commands or the parameters returned by the server in response to an EHLO command.

                             

                            Configuring a Logging Action for a Class Type in an SMTP Policy-Map

                            A logging action can be configured for a class type in an SMTP policy-map when conditions specified by the traffic class are met. The logging action results in a LOG_WARNING syslog message followed by the specific log message. The log message format is similar to other application firewall modules (for example, HTTP, IM, Peer-to-Peer (P2P)); session initiator/responder information, and zone-pair and class names.


                            Note


                            The log action currently exists for other types of policy-maps (http, pop3).


                            SUMMARY STEPS

                              1.    enable

                              2.    configure terminal

                              3.    class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}

                              4.    match cmd verb {parameter | WORD}

                              5.    exit

                              6.    policy-map type inspect smtp policy-map-name

                              7.    class type inspect smtp class-map-name

                              8.    log


                            DETAILED STEPS
                               Command or ActionPurpose
                              Step 1 enable


                              Example:
                              Router> enable
                               

                              Enables privileged EXEC mode.

                              • Enter your password if prompted.

                               
                              Step 2 configure terminal


                              Example:
                              Router# configure terminal
                               

                              Enters global configuration mode.

                               
                              Step 3 class-map type inspect smtp {class-map-name | match-all class-map-name | match-any class-map-name}


                              Example:
                              Router(config)# class-map type inspect smtp c1
                               

                              Enters class-map configuration mode and creates a class map for the SMTP protocol.

                              • The class-map-name argument by itself specifies a single class-map.

                              • The match-all keyword and class-map-name argument places logical and all matching statements under this class map.

                              • The match-any keyword and class-map-name argument places logical or all matching statements under this class map.

                               
                              Step 4 match cmd verb {parameter | WORD}


                              Example:
                              Router(config-cmap)# match cmd verb ATRN
                               

                              Identifies and masks a service extension parameter in the EHLO server reply.

                              • The parameter argument specifies a parameter from the well-known EHLO keywords.

                              • The WORD argument specifies an extension which is not on the EHLO list.

                               
                              Step 5 exit 

                              Exits class-map configuration mode.

                               
                              Step 6 policy-map type inspect smtp policy-map-name


                              Example:
                              Router(config)# policy-map type inspect smtp p1
                               

                              Creates a Layer 7 SMTP policy map and enters policy-map configuration mode.

                               
                              Step 7 class type inspect smtp class-map-name


                              Example:
                              Router(config-pmap)# class type inspect smtp c1
                               

                              Configures an SMTP class-map firewall for SMTP inspection parameters.

                               
                              Step 8 log


                              Example:
                              Router(config-pmap)# log
                               

                              Logs an action related to this class-type in the SMTP policy map.

                               

                              Configuration Examples for Application Inspection and Control for SMTP

                              Example Creating a Pinhole for the SMTP Port

                              The following example shows a configuration without any Layer 7 SMTP policy that creates a pinhole only for the SMTP port. Any command sent to the server, including the EHLO command is accepted.

                              class-map type inspect smtp c1
                              match protocol smtp
                              policy-map type inspect smtp c1
                              	class type inspect smtp c1
                              		inspect

                              Note


                              No SMTP policy is configured by default. If an SMTP policy is not configured, then no SMTP inspection is done by default.


                              Example Preventing ESMTP Inspection

                              If a user decides to create a workable policy that is configured for SMTP inspection only, then it now needs to be explicitly specified in the policy.

                              The following example can be used to prevent ESMTP inspection:

                              class-map type inspect smtp c1
                              	match cmd verb EHLO
                              policy-map type inspect smtp c1
                              	class type inspect smtp c1
                              		mask

                              Example MIME E-Mail Format

                              The format of data being transmitted through SMTP is specified by using the MIME standard, which uses headers to specify the content-type, encoding, and the filenames of data being sent (text, html, images, applications, documents and so on). The following is an example of an e-mail using the MIME format:

                              From: "username2" <username2@example.com>
                              To: username3 <username3@example.com>
                              Subject: testmail
                              Date: Sat, 7 Jan 2006 20:18:47 -0400
                              Message-ID: <000dadf7453e$bee1bb00$8a22f340@oemcomputer>
                              MIME-Version: 1.0
                              Content-Type: image/jpeg;
                              name='picture.jpg' 
                              Content-Transfer-Encoding: base64

                              <base64 encoded data for the picture.jpg image>

                              In the above example, the “name=’picture.jpg’” is optional. Even without the definition, the image is sent to the recipient. The e-mail client of the recipient may display the image as “part-1” or “attach-1” or it may render the image in-line. Also, attachments are not ‘stripped’ from the e-mail. If a content-type for which reset action was configured is detected, an 5XX error code is sent and the connection is closed, in order to prevent the whole e-mail from being delivered. However, the remainder of the e-mail message is sent.

                              Additional References for Application Inspection and Control for SMTP

                              Related Documents

                              Related Topic

                              Document Title

                              Cisco IOS commands

                              Cisco IOS Master Command List, All Releases

                              Firewall commands

                              ESMTP firewall information.

                              ESMTP Support for Cisco IOS Firewall

                              Information for configuring an SMTP policy.

                              Zone-Based Policy Firewall

                              Standards and RFCs

                              Standard/RFC

                              Title

                              RFC 1869 and other SMTP RFC extensions apart from RFC 821

                              SMTP Service Extensions

                              Technical Assistance

                              Description

                              Link

                              The Cisco Support and Documentation website provides online resources to download documentation, software, and tools. Use these resources to install and configure the software and to troubleshoot and resolve technical issues with Cisco products and technologies. Access to most tools on the Cisco Support and Documentation website requires a Cisco.com user ID and password.

                              http:/​/​www.cisco.com/​cisco/​web/​support/​index.html

                              Feature Information for Application Inspection and Control for SMTP

                              The following table provides release information about the feature or features described in this module. This table lists only the software release that introduced support for a given feature in a given software release train. Unless noted otherwise, subsequent releases of that software release train also support that feature.

                              Use Cisco Feature Navigator to find information about platform support and Cisco software image support. To access Cisco Feature Navigator, go to www.cisco.com/​go/​cfn. An account on Cisco.com is not required.
                              Table 1 Feature Information for Application Inspection and Control for SMTP

                              Feature Name

                              Releases

                              Feature Information

                              Application Inspection and Control for SMTP

                              12.4(20)T

                              The Application Inspection and Control for SMTP feature provides an intense provisioning mechanism that can be configured to inspect packets on a granular level so that malicious network activity, related to the transfer of e-mail at the application level, can be identified and controlled. This feature qualifies the Cisco IOS firewall extended SMTP (ESMTP) module as an “SMTP application firewall,” which protects in a similar way to that of an HTTP application firewall.

                              The following commands were introduced or modified by this feature: log (policy-map and class-map) , mask (policy-map), match body regex, match cmd, match header length gt, match header regex, match mime content-type regex, match mime encoding, match sender address regex, match recipient address regex, match recipient count gt, match recipient invalid count gt, match reply ehlo, reset (policy-map).

                              Glossary

                              C3PL --Cisco Common Classification Policy Language. Structured, feature-specific configuration commands that use policy maps and class maps to create traffic policies based on events, conditions, and actions.

                              EHLO --Extended HELO substitute command for starting the capability negotiation. This command identifies the sender (client) connecting to the remote SMTP server by using the ESMTP protocol.

                              ESMTP --Extended Simple Mail Transfer Protocol. Extended version of the Simple Mail Transfer Protocol (SMTP), which includes additional functionality, such as delivery notification and session delivery. ESMTP is described in RFC 1869, SMTP Service Extensions.

                              HELO --Command that starts the SMTP capability negotiation. This command identifies the sender (client) connecting to the remote SMTP server by its fully qualified DNS hostname.

                              MAIL FROM --Start of an e-mail message that identifies the sender e-mail address (and name, if used), which appears in the From: field of the message.

                              MIME --Multipurpose Internet Mail Extension. Standard for transmitting nontext data (or data that cannot be represented in plain ASCII code) in e-mail, such as binary, foreign language text (such as Russian or Chinese), audio, or video data. MIME is defined in RFC 2045.

                              RCPT TO --Recipient e-mail address (and name, if used) that can be repeated multiple times for a likely message to deliver a single message to multiple recipients.

                              SMTP --Simple Mail Transfer Protocol. Internet protocol providing e-mail services.