Random undeliverable with no bad recipients

[Bob]

I am helping someone with a problem that is puzzling. This person is using
Outlook 2007 at home with a GMail mail account.

Sometimes when she sends an e-mail to multiple recipients, she gets an NDR
as follows:
-------------------------
From: System Administrator
Sent: Monday, May 17, 2010 10:36 AM
To: Sender's name
Subject: Undeliverable: FW: Subject of Message

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

Subject: FW: Subject of Message

Sent: 5/17/2010 10:36 AM


The following recipient(s) cannot be reached:
-------------------------------
Tha's it. There are no recipients listed. When I go to "View - Options"
there are no headers. That would lead me to assume that Outlook itself is
creating this NDR rather than GMail's server or one of the recipients' mail
servers.

Any ideas?

Bob

 

[Brian Tillman [MVP-Outlook]]

I am helping someone with a problem that is puzzling. This person is using
Outlook 2007 at home with a GMail mail account.

Sometimes when she sends an e-mail to multiple recipients, she gets an NDR
as follows:
-------------------------
From: System Administrator
Sent: Monday, May 17, 2010 10:36 AM
To: Sender's name
Subject: Undeliverable: FW: Subject of Message

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

Subject: FW: Subject of Message

Sent: 5/17/2010 10:36 AM


The following recipient(s) cannot be reached:

Do you see the NDR in the gmail mailbox via a web browser?

 

[Bob]

Do you see the NDR in the gmail mailbox via a web browser?

No, it does not show up in the GMail inbox or "All Mail" folder.
I realized after I sent that that I should have included that tidbit. :-(

That was one of the reasons I was certain it must be coming from Outlook. I
didn't think that Outlook would do that?

Bob

 

[VanguardLH]

No, it does not show up in the GMail inbox or "All Mail" folder. I
realized after I sent that that I should have included that tidbit.
:-(

That was one of the reasons I was certain it must be coming from
Outlook. I didn't think that Outlook would do that?

You are probably using POP to access your e-mail account. Unless
configured otherwise, the default is to RETRieve a message and then
DELEte it. Enabling the "leave messages on server" eliminates the DELE
command. However, Gmail doesn't correctly follow POP standards. The
above is how POP should work. Gmail ignores the DELE commands and
instead uses the server-side user configurable option on how to handle
items that have been retrieved. You'll have to see how you configured
the POP settings in your Gmail account.

Does this "other person" have their e-mail client configured to
authenticate to Gmail's SMTP mail server?

This user also need to ensure that they are not included a null string
for a recipient (for example, by ending the To field with a comma which
would designate a following e-mail address but which might've been left
blank). That Gmail doesn't return a complete message with a delimited
string showing the rejected recipients is no big surprise. Could be
Gmail was told to send to a blank recipient, or the e-mail address was
invalid or no such account existed at the designated domain but Gmail
didn't show you the bad e-mail address. First see if authenticating to
the SMTP mail server fixes the problem, and that they are using the
correct port number.

 

[Bob]

You are probably using POP to access your e-mail account. Unless
configured otherwise, the default is to RETRieve a message and then
DELEte it. Enabling the "leave messages on server" eliminates the DELE
command. However, Gmail doesn't correctly follow POP standards. The
above is how POP should work. Gmail ignores the DELE commands and
instead uses the server-side user configurable option on how to handle
items that have been retrieved. You'll have to see how you configured
the POP settings in your Gmail account.

Does this "other person" have their e-mail client configured to
authenticate to Gmail's SMTP mail server?

This user also need to ensure that they are not included a null string
for a recipient (for example, by ending the To field with a comma which
would designate a following e-mail address but which might've been left
blank). That Gmail doesn't return a complete message with a delimited
string showing the rejected recipients is no big surprise. Could be
Gmail was told to send to a blank recipient, or the e-mail address was
invalid or no such account existed at the designated domain but Gmail
didn't show you the bad e-mail address. First see if authenticating to
the SMTP mail server fixes the problem, and that they are using the
correct port number.
.

That last is a real good idea. I will go back and peruse her sent mail and
check the addressing. She is the type of person who might do something like
that if you know what I mean.

We have her Gmail account set up to remove POPed mail from the Inbox and
archive it (moves it to the all mail folder) just in case she deletes
something.
And yes, she authenticates on the SMTP. Other e-mails go out fine, and it
isn't all multi-recipient messages that do this.

Thanks. for your thoughts.

Bob

 

[Bob]

You are probably using POP to access your e-mail account. Unless
configured otherwise, the default is to RETRieve a message and then
DELEte it. Enabling the "leave messages on server" eliminates the DELE
command. However, Gmail doesn't correctly follow POP standards. The
above is how POP should work. Gmail ignores the DELE commands and
instead uses the server-side user configurable option on how to handle
items that have been retrieved. You'll have to see how you configured
the POP settings in your Gmail account.

Does this "other person" have their e-mail client configured to
authenticate to Gmail's SMTP mail server?

This user also need to ensure that they are not included a null string
for a recipient (for example, by ending the To field with a comma which
would designate a following e-mail address but which might've been left
blank). That Gmail doesn't return a complete message with a delimited
string showing the rejected recipients is no big surprise. Could be
Gmail was told to send to a blank recipient, or the e-mail address was
invalid or no such account existed at the designated domain but Gmail
didn't show you the bad e-mail address. First see if authenticating to
the SMTP mail server fixes the problem, and that they are using the
correct port number.
.

BINGO! You lead me to find the problem. I checked the addresses on the
message in the GMail web interface and everything looked fine. Then, I
selected to show the original header, and found a name in the list without an
e-mail address with it. That would sure do this.

Thanks again.

Bob