Bad address in BCC causes rest of recipients to fail

[jvalley967]

Symptom:
Email sent to list of people is not received by some or all of the
list.

Diagnosis:
Entourage fails to send mail to subsequent BCC addresses, if an address
is malformed, when using Exchange.

Environment:
Entourage 2004, patched to 11.03 (Entourage version 11.2.5)
OS X 10.3.9, 10.4.8 (appears unrelated).
Exchange client mode, Exchange 2003.

This does not happen when used in POP mode, only in Exchange Client
mode.

If you have a list of 10 address in the BCC field and the second
address is malformed (two @ symbols, extra periods, extra "<") the
message will be sent to the first recipient but not to the bad address
(expected) and it will also _not_ be sent to the remaining 8 recipients
(unexpected). There are no status delivery failure notifications
either, from the client or server.

Bogus domains/addresses are not the issue here, just improperly typed
addresses.
(e-mail address removed) will eventually bounce as expected
[email protected] will cause the failure

Using a group with the "hide names" option checked automatically puts
the addresses in the BCC field which experiences the same behavior.

Have not been able to replicate the issue in Outlook nor in WebMail
(OWA lite).
As mentioned above, Entourage in POP mode does not have this issue.

Could not find anything on MS's Support site nor the Google archive of
the newsgroup. There was one entry on the Newsgroup indicating a
similar problem that required fixing the offending address, but it was
unclear what their exact symptom/config was. I have not contacted MS
yet.

Enabling the "check names" function in the General Preferences has no
impact.

Our current solution is to find the bad address and fix it, the trick
is knowing you have a failure. Obviously adding your own address to the
very end of a list will help in troubleshooting, training all of our
Users to do this correctly and then NOT sort the list is problematic.
Ideally we would get an error from Entourage or from the Exchange
server indicating which address was malformed. Currently it does not
appear to be server related, it appears to be Entourage related.

Can anyone confirm this behavior and/or know of a solution?

Our issue is that we are moving from Eudora to Entourage for all Staff
and (it would appear that) there are many mistakes being made on the
new address book groups as they are being created. As there is no
warning or other error Staff sending mail do not know the message has
not reached it's intended recipients (like the parents of the Teacher's
students).

/Jeramey

 

[GodSpace ~ Catholic Books, Gifts & Music]

Symptom:
Email sent to list of people is not received by some or all of the
list.

Diagnosis:
Entourage fails to send mail to subsequent BCC addresses, if an address
is malformed, when using Exchange.

<snip>
Bogus domains/addresses are not the issue here, just improperly typed
addresses.
(e-mail address removed) will eventually bounce as expected
[email protected] will cause the failure

Using a group with the "hide names" option checked automatically puts
the addresses in the BCC field which experiences the same behavior.

Have not been able to replicate the issue in Outlook nor in WebMail
(OWA lite).
As mentioned above, Entourage in POP mode does not have this issue.

Enabling the "check names" function in the General Preferences has no
impact.

Can anyone confirm this behavior and/or know of a solution?

/Jeramey

Jeramey - if you get a response - I would be ECSTATIC to know also, as this
is a bane of my existence also. POP, which is all I use, does have this
problem also.

AS AN ASIDE, what is the max # of addys "allowed" in bcc. Verizon kicks at

100, my personal ISP doesn't at all. How do others email customers? I now

have them broken into 3 groups and resend the mail 3 times, b/c I need to
use the verizon addy.

 

[Michel Bintener]

AS AN ASIDE, what is the max # of addys "allowed" in bcc. Verizon kicks at
have them broken into 3 groups and resend the mail 3 times, b/c I need to
use the verizon addy.

Instead of resending a message a couple of times, you could also use Paul
Berkowitz' free AppleScript "Split Recipient X"
<http://scriptbuilders.net/files/splitrecipientsxforentouragex2.0.html>.
That way, you write the message only once and let the script do the
splitting for you.

--
Michel Bintener
Microsoft MVP
Office:Mac (Entourage & Word)

***Always reply to the newsgroup.***

 

[Allen Watson]

Symptom:
Email sent to list of people is not received by some or all of the
list.

Diagnosis:
Entourage fails to send mail to subsequent BCC addresses, if an address
is malformed, when using Exchange.

In my experience there IS an error generated, but it often isn't apparent to
the user. When sending to large groups, make a practice of typing ⌘-8
afterwards to view the Error Log. (If it does nothing, there is no error log
file to view.) That file often contains an indication of which address
failed.

The "check names" preference only works with addresses that are in the local
LDAP server (if there is one), addresses you might enter without domain
name, e.g., "mike" instead of "(e-mail address removed)". Not useful for general
address checking.

If you open the sent message after an error occurs, and open up the BCC
list, I believe you should also see an error icon or warning icon next to
the offending address.

I'm wondering if this is a problem unique to using the BCC field? Have you
tried sending out a message with multiple addresses in the To or CC fields,
with an invalid one in the middle? See if your message is delivered to all
but the invalid address. That has been my experience using POP mail; I don't
have access to an Exchange account.

 

[jvalley967]

In my experience there IS an error generated,

Nope, not here. There is specifically no error (including in any logs
generated such as those available via command-8). No error when used in
Exchange Client mode, errors shown in other modes during testing.

If you open the sent message after an error occurs, and open up the BCC
list, I believe you should also see an error icon or warning icon next to
the offending address.

Nope again.

I'm wondering if this is a problem unique to using the BCC field?

Correct, please see original post - this only happens when used in
Exchange mode. Chaging the account to POP or IMAP (going to the same
mail server or a different one) produces the type of errors you would
expect such as "bad address".

Thanks for the reply.