totalnetsolutions.net

I recently had a co-worker trying to figure out a “lost email” problem we were possibly experiencing. He was blind to everything after hitting “send” because the intermediate servers weren’t sending delivery recipets, even though they were requested in the MIME header (Does any mail admin allow those to be sent out of the organization these days?) So, to help him out, I wrote up the following “how to test SMTP by hand” HOWTO.

First step is to determine which servers are responsible for mail delivery inbound for the domain you’re sending to. You do this by looking in DNS for the “MX” type records. These are provided in the format “priority servername.domain.” Priority is reverse-ordered. The easiest way to remember priority order is that it’s the order in which servers are attempted.

rob@rob-kubuntu3:~$ dig MX totalnetsolutions.net +short
10 docsmooth.isa-geek.net.
rob@rob-kubuntu3:~$ dig MX likewise.com +short
10 server1.inboundmx.com.
20 server2.inboundmx.com.

This tells you the servers, in order, that *all* mail will be sent to for the domain listed. So, anything to my likewise.com address will go to server1.inboundmx.com. The higher priorities are only used if the lower priorities fail to answer. If no server answers, the mail is held by the sender and retried, generally every 1 or 4 hours for up to 4 days, but this retry is configured on the *sending* server. That means, your own email admin (or you, if you’re the mail admin).

Next thing to check is: does the server work, and is it your sender, or their receiver? Check with telnet!
Stuff I type is in red:

rob@rob-kubuntu3:~$ telnet docsmooth.isa-geek.net 25
Trying 99.29.179.119...
Connected to docsmooth.isa-geek.net.
Escape character is '^]'.
220 totalnetsolutions.net Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Tue, 31 May 2011 08:43:08 -0500
HELO
250 totalnetsolutions.net Hello [12.130.116.175]
MAIL FROM: me@me.com
250 2.1.0 me@me.com....Sender OK
RCPT TO:you@you.net
250 2.1.5 you@you.net
DATA
354 Start mail input; end with .
from:me@me.com
to:you@you.net
subject:test manually
test
test
.
250 2.6.0 Queued mail for delivery
quit
221 2.0.0 totalnetsolutions.net Service closing transmission channel
Connection closed by foreign host.

The last “.” is SUPER important – it tells the mail server when you’re done sending that email. You could use that channel to send other messages, rather than sending “QUIT” if you’d like. You might notice that I entered the “From” and “To” lines twice. The first entries are for the SMTP header (analogy would be the message envelope), and the second entries are for the MIME headings (analogy would be the return address header in a formal postal letter, if anyone sends those). The MIME headings are what most mail programs display, and actually don’t technically need to match the SMTP header (but if MIME and SMTP don’t match many anti-spam programs will throw out the message).

The MIME header is pretty complex, but not order-dependant, although I prefer to enter it in order, so that I can be sure I don’t miss anything.
If you want to add an attachment, just base64 encode it first with:
perl -e 'use MIME::Base64; qw(encode_base64); print encode_base64("@ARGV");' cat attachment-to-send.zip
Then you can just paste it into the email. In the MIME heading (right after the subject), just add (with the appropriate mime coding, probably application/octet-string:

------=_NextPart_000_000D_01CC1C41.21F38080
Content-Type: application/zip;
name="attachment-to-send.zip"
Content-Transfer-Encoding: base64
Content-Disposition: attachment;
filename="attachment-to-send.zip"
<paste your base64 encoded attachment/ >
Content-Type: multipart/mixed;
boundary="----=_NextPart_000_000D_01CC1C41.21F38080"
------=_NextPart_000_000D_01CC1C41.21F38080
Content-Type: text/plain;
charset="us-ascii"
Content-Transfer-Encoding: 7bit

Now that you know *how* to send an email message by hand, you can use the returned error codes to troubleshoot where the message may be disappearing. Remember, that this just gives you transport troubleshooting between yourself and the initial destination mail server. Many large (and even medium-sized) organizations will have a perimeter mail server which then forwards the message to one or more internal servers. If the mail is being dropped at that point, you’ll have to contact the reciever with the proof that their server is accepting your messages.