08-19-2009
If you have a smarthost defined, the email will be sent to your smarthost then on to the destination. If you are sending directly to the other host there are ways to debug it. First, do a lookup to find the MX (Mail eXchange) record for the domain.
dig -t mx jimbob.com.
Once you find out who the mail exchanger is, you could try to telnet to port 25 of that host which is the SMTP port and see if it responds.
You should also be able to look at the sendmail logs '/var/log/maillog' to see what is going on with the jimbob.com emails. See if they were sent on or if they are still sitting on your host waiting to be delivered.
I did have an instance a while back where a business changed ISPs. Any customer using the old ISP, still was getting the old MX record back instead of the current one. This is because the ISP did not delete the old MX record once the domain left their control.
You may also have a routing problem where you just can't get to the destination SMTP server. You may also have a case where the destination server is using anti-spam protection and your server or the range of IP addresses it uses were defined as SPAM senders and the destination server is not accepting a connection from you.
You might also try traceroute to the destination SMTP server to see if that works.
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LEARN ABOUT OSF1
mconnect
mconnect(1) User Commands mconnect(1)
NAME
mconnect - connect to SMTP mail server socket
SYNOPSIS
mconnect [-p port] [-r] [hostname]
DESCRIPTION
The mconnect utility opens a connection to the mail server on a given host, so that it can be tested independently of all other mail soft-
ware. If no host is given, the connection is made to the local host. Servers expect to speak the Simple Mail Transfer Protocol (SMTP) on
this connection. Exit by typing the quit command. Typing EOF sends an end of file to the server. An interrupt closes the connection immedi-
ately and exits.
OPTIONS
The following options are supported:
-p port Specify the port number instead of the default SMTP port (number 25) as the next argument.
-r "Raw" mode: disable the default line buffering and input handling. This produces an effect similar to telnet(1) to port
number 25.
OPERANDS
The following operand is supported:
hostname The name of a given host.
USAGE
The mconnect command is IPv6-enabled. See ip6(7P).
FILES
/etc/mail/sendmail.hf help file for SMTP commands
ATTRIBUTES
See attributes(5) for descriptions of the following attributes:
+-----------------------------+-----------------------------+
| ATTRIBUTE TYPE | ATTRIBUTE VALUE |
+-----------------------------+-----------------------------+
|Availability |SUNWcsu |
+-----------------------------+-----------------------------+
SEE ALSO
telnet(1), sendmail(1M), attributes(5), ip6(7P)
Postel, Jonathan B., RFC 821, Simple Mail Transfer Protocol, Information Sciences Institute, University of Southern California, August
1982.
SunOS 5.10 9 Nov 1999 mconnect(1)