UNDELIVERABLE MAIL: MS OUTLOOK 2003

[Natalie]

Hi
I get this error message when I try to send mail from my outlook 2003
account.

Your message did not reach some or all of the intended recipients.

Subject: FW: Contract issues - CARRIER WARRANTY CHECKS - STATUS UPDATE
Sent: 8/21/2009 10:41 AM

The following recipient(s) could not be reached:

'(e-mail address removed)' on 8/21/2009 10:41 AM

503 Valid RCPT command must precede DATA

This is happening to most of the emails I send. How can I fix this so I can
send emails?

Thanks

Natalie

 

[K. Orland]

Apparently this occurs when a server is expecting to receive mail before
sending. This is usually results from server authentication priorities (for
example, you attempt to send mail before your "spam filter" has finished its
receiving process.)

You must receive mail before you can send it.

Solution: POP before SMTP.

a.. Run a check for new messages (F9 key in Outlook) before sending your
message and restart and rerun your spam filter application. Your IP address
is entered in a relayhosts file, allowing email to be sent from your address
for up to half an hour.
a..
a.. If the problem still persists check "my server requires authentication"
to authenticate automatically. With this setting you can bypass the check
above and send mail without having to "pop" your mail box first. You can
also try changing the outgoing port from 25 to 587, since some ISP's block
this port.

 

[Brian Tillman [MVP - Outlook]]

I get this error message when I try to send mail from my outlook 2003
account.

Your message did not reach some or all of the intended recipients.

Subject: FW: Contract issues - CARRIER WARRANTY CHECKS - STATUS UPDATE
Sent: 8/21/2009 10:41 AM

The following recipient(s) could not be reached:

'(e-mail address removed)' on 8/21/2009 10:41 AM

503 Valid RCPT command must precede DATA

Two of the common causes of this are 1) not properly authenticating to the
outgoing server and 2) scanning your outbound mail with an antivirus program.
In the former case, consult your mail provider's help pages. In the latter
case, uninstall the AV program and reinstall it without the mail scanning
feature.

 

[VanguardLH]

Apparently this occurs when a server is expecting to receive mail before
sending.

The RCPT-TO command is how the SMTP server to whom the message gets
sent. For an aggregate of N recipients in the To, CC, and Bcc *fields*
in the UI for the e-mail client, the e-mail client sends a RCPT-TO
command for each recipient followed by a single DATA command that
contains the message (user/client headers, blank delimiter line, and
body). The RCPT-TO *must* be sent for the SMTP server to know where to
send your e-mail. So, using the example above, you should see N RCPT-TO
headers for the N total recipients and a DATA command (ended with a line
with a single dot to delimit the length of the message):

login/auth commands (USER, PASS)
....
RCPT TO <recipient1>
RCPT TO <recipient2>
....
DATA
<your message = headers, blank line, body>
..

 

[VanguardLH]

Hi
I get this error message when I try to send mail from my outlook 2003
account.

Your message did not reach some or all of the intended recipients.

Subject: FW: Contract issues - CARRIER WARRANTY CHECKS - STATUS UPDATE
Sent: 8/21/2009 10:41 AM

The following recipient(s) could not be reached:

'(e-mail address removed)' on 8/21/2009 10:41 AM

503 Valid RCPT command must precede DATA

This is happening to most of the emails I send. How can I fix this so I can
send emails?

Thanks

Natalie

See my reply to Orland. What you see in the UI for your e-mail client
is not what gets sent to the mail server. There is an e-mail protocol
to follow. From the To, Cc, and Bcc *fields* displayed in your e-mail
client, a compiled list is created from the aggregate of all those input
fields. For N recipients, N RCPT-TO commands will get sent to the SMTP
mail server to tell it to whom your single message gets sent. That is
followed by a DATA command that contains your message (headers, blank
line, and body).

If the RCPT-TO headers are missing then the SMTP server is not being
told who are the recipients of your e-mail. It cannot deliver your
message unless it knows to where to send it. Something is corrupting
your e-mail traffic to the SMTP mail server. You either have an add-on
that is screwing up the e-mail traffic or something upstream of your
e-mail client is interrogating it and screwing up its content.

See what happens when you load Outlook in its safe mode which eliminates
loading any add-ons that might affect the behavior of Outlook. Run:

outlook.exe /safe

If that doesn't help, disable any e-mail scanning in whatever anti-virus
program you use. It is superfluous protection for inbound e-mail. It
is absolutely pointless for outbound e-mail as far as the recipient is
concerned. Some text added to an e-mail claiming it is virus-free is
NOT going to be believed by a recipient who should be using their own
anti-virus software to use its on-access scanner for anything saved out
of their e-mails.

Some anti-virus programs do not get out of the way when you disable
their e-mail scanning function. Your e-mail traffic still goes through
their transparent proxy but doesn't go through interrogation; however,
if their proxy screws up then so, too, is your e-mail traffic. You have
to uninstall the anti-virus program and then do a *custom* install where
you elect to NOT include their e-mail scanner.

Some anti-virus programs act like a mail server. Rather than
interrogate your e-mail traffic on-the-fly, they grab the entire e-mail
as though your client had sent it to the actual mail server. Since your
e-mail client sees a successful send, it shows no error. The AV program
grabbed all of your e-mail and, independent of your e-mail client, then
sends it onto the real mail server. If there is an error between the AV
program and the real mail server, your e-mail client won't see it since
it isn't involved anymore. I think McAfee's ViruScan is like this.
Your e-mail client won't see any errors from the SMTP server because it
never actually connected to the SMTP server. It instead connected to
the local mail "server" for the AV program. If you want to see if there
are errors between the AV's pseudo-server (looks like a server to your
client and looks like a client to the real server), you have to go look
at its logs.

Inbound AV scanning on e-mail is superfluous. It duplicates the same
check that the AV's on-access (real-time) scanner performs if and when
you save anything out of an e-mail, like an attachment. E-mail scanning
does, however, move earlier the detection but doesn't increase the level
of protection. The delays it causes can incur timeouts at the client or
server, especially noticeable for dial-up connections and/or for large
e-mails (i.e., those with huge attachments).

Outbound AV scanning doesn't make any sense. No one is going to believe
some blurb added to an e-mail that claims it is virus free. If your AV
on-access scanner (and on-demand scanner for scheduled scans) didn't
catch the malware, well, it's the same stuff being used to scan your
outbound e-mails. If it wasn't caught on your host, it won't get caught
in your outbound e-mails, either.

Get rid of e-mail scanning. It affords no additional protection but
often causes timeouts, corrupted e-mail traffic, having to check logs
between the AV and mail server (since the client never did connect to
the mail server), and other problems.