Trace Outbound Mail SMTP Sessions from the ESA

Introduction

This document describes how to trace and view an entire email conversation from your Cisco Email Security Appliance (ESA).

Trace Outbound Mail SMTP Sessions Per Recipient Domain

The domain debug logs allow you to trace an entire Simple Mail Transfer Protocol (SMTP) conversation between your ESA and the destination domain/host. Each line in the domain debug log outlines the data that is sent (Sent) and received (Rcvd) during the SMTP conversation.

Enter the logconfig command into the ESA CLI in order to configure the logging so that the ESA records a domain debug log for the recipient domain of interest:

Choose the operation you want to perform:
- NEW - Create a new log.
- EDIT - Modify a log subscription.
- DELETE - Remove a log subscription.
- SETUP - General settings.
- LOGHEADERS - Configure headers to log.
- HOSTKEYCONFIG - Configure SSH host keys.
[]> new

Choose the log file type for this subscription:
1. IronPort Text Mail Logs
2. qmail Format Mail Logs
3. Delivery Logs
4. Bounce Logs
5. Status Logs
6. Domain Debug Logs
7. Injection Debug Logs
8. SMTP Conversation Logs
9. System Logs
10. CLI Audit Logs
11. FTP Server Logs
12. HTTP Logs
13. NTP logs
14. LDAP Debug Logs
15. Anti-Spam Logs
16. URL Filtering Logs
17. Graymail Engine Logs
18. Anti-Spam Archive
19. Anti-Virus Logs
20. Anti-Virus Archive
21. Scanning Logs
22. Spam Quarantine Logs
23. Spam Quarantine GUI Logs
24. Reporting Logs
25. Reporting Query Logs
26. Updater Logs
27. SNMP Logs
28. Tracking Logs
29. Safe/Block Lists Logs
30. Authentication Logs
31. FIPS Logs
32. Upgrade Logs
33. Configuration History Logs
34. Reputation Engine Logs
35. AMP Engine Logs
36. AMP Archive
37. API Logs
38. Graymail Archive
[1]> 6

Please enter the name for the log:
[]> example.com.domain.debug

Enter the name of the domain for which you want to record
 debug information.
[]> example.com

Please enter the number of SMTP sessions you want to record
 for this domain.
[1]> 10000

Choose the method to retrieve the logs.
1. Download Manually: FTP/HTTP(S)/SCP
2. FTP Push
3. SCP Push
4. Syslog Push
[1]> 

Filename to use for log files:
[example.com.text]> 

Would you like to append system based unique identifiers
 like $hostname, $serialnumber to the log filename? [N]> 

Please enter the maximum file size. You can specify suffixes:
 "m" for megabytes, "k" for kilobytes. Suffixes are
 case-insensitive:
[10485760]> 

Please enter the maximum number of files:
[10]> 

Should an alert be sent when files are removed due to the
 maximum number of files allowed? [N]> 

Do you want to configure time-based log files rollover? [N]> 

Note: Ensure that you commit any and all changes after the domain debug log is configured.

The log is active for the number of sessions that you configure for the domain. In order to view the trace of the live email conversation, enter the tail example.com.domain.debug command into the ESA CLI.

Here is an example domain debug log that is generated when the ESA delivers a message to the recipient domain example.com:

Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '220 ESmtp mail.example.com ESMTP service
 ready'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'EHLO example.com'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250-mail.example.com'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250-8BITMIME'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250-SIZE 31981568'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250 PIPELINING'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'MAIL FROM:<user@example.com>'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250 sender <user@exmple.com> ok'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'RCPT TO:<test@example.com>'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250 recipient <test@example.com> ok'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'DATA'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '354 go ahead'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'Received: from unknown (HELO)(10.250.7.164)
 \r\n by example.com with SMTP; 22 Mar 2005 16:52:08 -0800\r\n'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: 'Message-ID:
 <000d01c52f43$48dacba0$a407fa0a@example.com>\r\nFrom: "User"
 <user@example.com>\r\nTo:<test@example.com>\r\n Subject:Test\r\nDate:
 Tue,22Mar200516:57:28-0800\r\nMIME-Version:1.0\r\n
Content-Type:multipart/alternative;\r\n\tboundary="----=_Next
Part_000_000A_01C52F00.3AA3B580"\r\nX-Priority: 3\r\nX-MSMail-Priority: Normal\r\n
X-Mailer: Microsoft Outlook Express 6.00.2900.2180\r\nX-MimeOLE: Produced ByMicrosoft
 MimeOLEV6.00.2900.2180\r\n\r\nThis is a multi-part messageinMIMEformat.\r\n\r\
 n------=_NextPart_000_000A_01C52F00.3AA3B580\r\nContent-Type:text/plain;\r\n\
 tcharset= "iso-8859-1"\r\nContent-Transfer-Encoding: quoted-printable\r\n\r\nThis
 is the body of the mail.\r\nThis isadisclaimer.\r\n\r\n------=
 _NextPart_000_000A_01C52F00.3AA3B580\r\nContent-Type:text/html;\r\n\tcharset=
 "iso-8859-1"\r\nContent-Transfer-Encoding: quoted-printable\r\n\r\n<!DOCTYPE HTML
 PUBLIC"-//W3C//DTDHTML4.0Transitional//EN">\r\n<HTML><HEAD>\r\n<METAhttp-equiv=
 3DContent-Typecontent= 3D"text/html;charset= 3Diso-8859-1">\r\n<METAcontent=3D"
 MSHTML6.00.2900.2523"name= 3DGENERATOR>\r\n<STYLE></STYLE>\r\n</HEAD>\r\n
 <BODYbgColor= 3D#ffffff>\r\n<DIV><FONTface= 3DArialsize= 3D2>This is the body of
 the\r\nmail.</FONT></DIV><pre> This is a disclaimer.\r\n </pre></BODY></HTML>\r\n\r\
 n------=_NextPart_000_000A_01C52F00.3AA3B580--\r\n'
Tue Mar 22 16:52:07 2005 Info: 411 Sent: '.\r\n'
Tue Mar 22 16:52:07 2005 Info: 411 Rcvd: '250 ok dirdel'
Tue Mar 22 16:52:12 2005 Info: 411 Sent: 'QUIT'
Tue Mar 22 16:52:12 2005 Info: 411 Rcvd: '221 mail.example.com'

Related Information

• Cisco Email Security Appliance – End-User Guides
• ESA Domain Debug Logs Configuration Example
• ESA FAQ: How do you analyze intermittent mail delivery issues on the ESA?
• Technical Support & Documentation – Cisco Systems