Email stuck in Outbox

[JC]

Hi,

About 3 days ago I had a couple of emails stuck in the outbox. I was
able to receive emails ok and send other emails but these two emails
were stuck in the outbox and refused to be sent. I shut down Outlook
2003, re-booted Win Xp (all updates installed) and re-started Outlook
but nothing changed.

The error was 0x8004210B - timed out waiting for response from SMTP
server.

It took a while to find the cause - apparently a mail server due to
receive one of the emails was down and, since it wouldn't receive mail,
all emails with an email address on that server would not be sent.

Note that it wasn't my ISPs mail server that was down - it was another
mail server in another country.

The problem email address was a Cc: so I deleted the problem address and
both emails then were sent ok.

It would appear that an email is ONLY sent if all mail servers that are
to receive the email are up and operational - if one is down it stays in
the outbox presumably until the server is brought back on line again.

I would have preferred that the email be sent out to those mail servers
that were operational and an error message sent to me saying that the
following email could not be delivered to <address> because the server
was not on line.

 

[Peter Foldes]

Is there still a problem ?? I cannot tell . Or did you just post to tell us about your incident and how it was solved

 

[JC]

I don't have the problem now.

Basically, I posted about this incident to let others know about it and
to see if this is the way emails are normally handled by the servers.

 

[Brian Tillman]

It would appear that an email is ONLY sent if all mail servers that
are to receive the email are up and operational - if one is down it
stays in the outbox presumably until the server is brought back on
line again.

The error you received would only happen if you were to attempt connection
directly from your Outlook client to the server that is down. Otherwise,
that's simply not the way SMTP mail routing works. If your ISP's server is
up, it will accept the mail from you no matter what the condition of other
servers in the world. Only if your ISP's SMTP server won't accept the
message will you get the error you describe.

 

[VanguardLH]

in message

Hi,

About 3 days ago I had a couple of emails stuck in the outbox. I
was
able to receive emails ok and send other emails but these two emails
were stuck in the outbox and refused to be sent. I shut down
Outlook
2003, re-booted Win Xp (all updates installed) and re-started
Outlook
but nothing changed.

The error was 0x8004210B - timed out waiting for response from SMTP
server.

It took a while to find the cause - apparently a mail server due to
receive one of the emails was down and, since it wouldn't receive
mail,
all emails with an email address on that server would not be sent.

Note that it wasn't my ISPs mail server that was down - it was
another
mail server in another country.

The problem email address was a Cc: so I deleted the problem address
and
both emails then were sent ok.

It would appear that an email is ONLY sent if all mail servers that
are
to receive the email are up and operational - if one is down it
stays in
the outbox presumably until the server is brought back on line
again.

I would have preferred that the email be sent out to those mail
servers
that were operational and an error message sent to me saying that
the
following email could not be delivered to <address> because the
server
was not on line.

Sorry, but Outlook is only an e-mail *client*. It has no information
if the target mail hosts are reachable, responsive, and will accept
your e-mail that is sent to them. Your sending mail server handles
that, not you in your local e-mail client. The only status of which
Outlook has direct knowledge is whether or not YOUR mail server
accepted your outbound e-mail.

When you send e-mail to an SMTP mail host, just ONE copy of your
message gets sent to it, not one for each recipient. From the
recipients listed in your To, Cc, and Bcc *fields* (displayed in your
e-mail client), your e-mail client then compiles a list of RCPT-TO
commands that it sends to the mail host. For N recipients total,
there will be N RCPT-TO commands sent to your mail host. That is
following by just one DATA command from your e-mail client that
contains the content of your message that is received by your mail
host. All your e-mail client does it give the list of recipients and
a copy of your message to your mail host. During YOUR mail session
with your sending mail host, your mail hasn't been sent anywhere yet
other between you and your own mail host. It has not been sent out to
anyone yet, so the mail host doesn't send back any status regarding
its delivery since it hasn't been attempted to be delivered yet.
After you *end* your mail session with you mail host is when your mail
host then attempts delivery because it now has the list of recipients
and a copy of your message to them. You no longer have a session with
your mail host when your mail host is doing the actual delivery
attempts.

So, to how many recipients were specified in your e-mail? Maybe you
hit your e-mail provider's anti-spam quota. Deleting some of the
recipients got it under that anti-spam quota.

Did you try disabling your anti-virus software's scanning of your
outbound e-mails? Interrogation by the anti-virus software generates
a delay from when your e-mail client tells the mail server when it
will start sending your e-mail to when the e-mail actually arrives at
the mail server, and anti-virus software can interfere by increasing
this delay too much (i.e., the mail server timesout waiting for the
mail it was told was going to be sent but which was overly delayed by
your anti-virus program). The bigger the e-mail, the longer it takes
for your anti-virus program to interrogate it before handing it off to
the mail server.

 

[JC]

The error you received would only happen if you were to attempt connection
directly from your Outlook client to the server that is down. Otherwise,
that's simply not the way SMTP mail routing works. If your ISP's server is
up, it will accept the mail from you no matter what the condition of other
servers in the world. Only if your ISP's SMTP server won't accept the
message will you get the error you describe.

I am only connecting to my ISPs mail server.

Why did the emails go out when I deleted the second email address?

Note: I have been able to send emails out containing both email
addresses both before and since this incident.

 

[JC]

in message



Sorry, but Outlook is only an e-mail *client*. It has no information
if the target mail hosts are reachable, responsive, and will accept
your e-mail that is sent to them. Your sending mail server handles
that, not you in your local e-mail client. The only status of which
Outlook has direct knowledge is whether or not YOUR mail server
accepted your outbound e-mail.

When you send e-mail to an SMTP mail host, just ONE copy of your
message gets sent to it, not one for each recipient. From the
recipients listed in your To, Cc, and Bcc *fields* (displayed in your
e-mail client), your e-mail client then compiles a list of RCPT-TO
commands that it sends to the mail host. For N recipients total,
there will be N RCPT-TO commands sent to your mail host. That is
following by just one DATA command from your e-mail client that
contains the content of your message that is received by your mail
host. All your e-mail client does it give the list of recipients and
a copy of your message to your mail host. During YOUR mail session
with your sending mail host, your mail hasn't been sent anywhere yet
other between you and your own mail host. It has not been sent out to
anyone yet, so the mail host doesn't send back any status regarding
its delivery since it hasn't been attempted to be delivered yet.
After you *end* your mail session with you mail host is when your mail
host then attempts delivery because it now has the list of recipients
and a copy of your message to them. You no longer have a session with
your mail host when your mail host is doing the actual delivery
attempts.

So, to how many recipients were specified in your e-mail? Maybe you
hit your e-mail provider's anti-spam quota. Deleting some of the
recipients got it under that anti-spam quota.

Did you try disabling your anti-virus software's scanning of your
outbound e-mails? Interrogation by the anti-virus software generates
a delay from when your e-mail client tells the mail server when it
will start sending your e-mail to when the e-mail actually arrives at
the mail server, and anti-virus software can interfere by increasing
this delay too much (i.e., the mail server timesout waiting for the
mail it was told was going to be sent but which was overly delayed by
your anti-virus program). The bigger the e-mail, the longer it takes
for your anti-virus program to interrogate it before handing it off to
the mail server.

The email was about 30 lines of text only. There were only 2 addresses
for the email to be sent to -
the To: address was (e-mail address removed) and the Cc address was
(e-mail address removed).

The (e-mail address removed) was the address that caused the emails to stay in
the outbox. Initially, I thought that the spam@ was causing a problem
with my ISP's spam filter so I called the help desk. I was told by the
help desk that this was unlikely and that they couldn't ping the
(e-mail address removed) domain. It was then that I tried deleting the
(e-mail address removed) address from the Cc field and out went the emails.

Note that I had sent similar emails to both addresses the previous day
and have been able to do so since the incident.

 

[VanguardLH]

in message

The email was about 30 lines of text only. There were only 2
addresses
for the email to be sent to -
the To: address was (e-mail address removed) and the Cc address was
(e-mail address removed).

The (e-mail address removed) was the address that caused the emails to stay
in
the outbox. Initially, I thought that the spam@ was causing a
problem
with my ISP's spam filter so I called the help desk. I was told by
the
help desk that this was unlikely and that they couldn't ping the
(e-mail address removed) domain. It was then that I tried deleting the
(e-mail address removed) address from the Cc field and out went the emails.

Note that I had sent similar emails to both addresses the previous
day
and have been able to do so since the incident.

If it happens again, check with your e-mail provider if the
destination domain is on their blacklist. It is possible that they
are filtering outbound e-mails against a blacklist. Not many do this
yet but some. If they do outbound spam blocking (to blacklisted
target domains) then maybe they check this during the mail session
between your e-mail client and your mail host (but I would think this
would overly slow down all the mail sessions so they would do this
after your mail session is over and when their mail host is ready to
send your message).

Got any anti-spam software running locally on your host?

 

[JC]

in message



If it happens again, check with your e-mail provider if the
destination domain is on their blacklist. It is possible that they
are filtering outbound e-mails against a blacklist. Not many do this
yet but some. If they do outbound spam blocking (to blacklisted
target domains) then maybe they check this during the mail session
between your e-mail client and your mail host (but I would think this
would overly slow down all the mail sessions so they would do this
after your mail session is over and when their mail host is ready to
send your message).

Got any anti-spam software running locally on your host?

Will do so. I have anti-spam and anti-virus checking being done on my
mail server but this would surely only affect incoming mail. I have
Norton AV running on my pc but, since I have been able to send before
and after the incident, I don't see this as influencing what happened.
In addition, Norton is running the same set of defs before, during and
after the incident - a new set of defs should be installed today.

I would expect that blacklists apply to incoming emails and not outgoing
emails. I've had emails blocked by the receiving mail server because
they are coming from my ISPs mail server or IP address space but I am
not aware of emails not being sent out because they are going to a
blacklisted mail server.

 

[Brian Tillman]

I am only connecting to my ISPs mail server.

Why did the emails go out when I deleted the second email address?

Note: I have been able to send emails out containing both email
addresses both before and since this incident.

Without seeing the exact text of the error, I cannot say, but I know how
SMTP mail works and the ONLY server your Outlook "talks" to is your ISP's
server.

 

[JC]

Without seeing the exact text of the error, I cannot say, but I know how
SMTP mail works and the ONLY server your Outlook "talks" to is your ISP's
server.

The error was 0x8004210B - timed out waiting for response from SMTP
server.

This makes some sense if my ISP's mail server checks all receiving mail
servers before taking the email from outlook. If one or more receiving
servers are down then it will time out and not collect the email from
Outlook. Does this make sense?

 

[Brian Tillman]

This makes some sense if my ISP's mail server checks all receiving
mail servers before taking the email from outlook. If one or more
receiving servers are down then it will time out and not collect the
email from Outlook. Does this make sense?

That is not very typical for how an SMTP router would work. I can't think
of any way a server could check a remote server before accepting the
incoming message in its entirety.