Syntax Error 5.5.2 when sending to multiple Recipients

[imikejackson]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: pop

I am trying to help someone out with a sending problem. Every time they create an email with more than 1 recipient and send it Entourage gives them a "Syntax 5.5.2" Error. She is trying to send a mass email announcing a recent email address change.

Is there a built in limit to the number of recipients that Entourage can handle?

She has setup a pop account with Google Apps for her own domain. We have followed all the setup instructions posted at Google to properly setup Entourage to access the servers.

Has anyone else seen this error? (Well, yes, there are lots of people _asking_ the question but no one ever replies with an answer).

Thanks for any help
Mike Jackson
Principal Software Engineer
BlueQuartz Software

 

[Thomas Wildgruber]

I am trying to help someone out with a sending problem.
Every time they create an email with more than 1 recipient
and send it Entourage gives them a "Syntax 5.5.2" Error.
She is trying to send a mass email announcing a recent
email address change.

This error message is coming from one of the involved MTAs. Can you post
the complete error message? Anyway, the 5.5.2 Message indicates several
problems.

One possibility is a too long RCPT TO command, which can occur when too
much recipients are in the TO line. The "Syntax Error" sounds in this
direction. Try it again with the other recipients in the CC line. Also try
a smaller number of recipients (20; 50; 100; 200 and so on). Microsoft
Exchange Server 2003 for example have a default maximum number of (AFAIK)
250 recipients but it's up to the admin to adjust this limit as he want.
This are server settings and if there is a limit reached, you can do
nothing without server control permissions. But Exchange Server normally
produce a 5.5.3 Error when the maximum number of recipiens is reached.

But there are much more reasons for a 5.5.2 Error. The complete error
message should contain more informations as "Syntax 5.5.2" If you can
reproduce this error with onne single recipient also or she is not able to
recieve or send any mails, or is only able to recieve mails, you should
check the configuration once again.

HTH Tom

 

[Adam Bailey]

I am trying to help someone out with a sending problem. Every time they
create an email with more than 1 recipient and send it Entourage gives them a
"Syntax 5.5.2" Error. She is trying to send a mass email announcing a recent
email address change.

Is it *every time* they create an email with more than one recipient,
or just this particular recipient list for the announcement?

Is there a built in limit to the number of recipients that Entourage can
handle?

No. The error you cite is one that's being generated by the ISP. Either
they have a limit, or - more likely - one of the email addresses in the
list has a syntax error. A space or a comma or some other illegal
character. Start pouring through the address list and find the one that
is wrong. Maybe break the mailing up into multiple batches until you
find one that is broken.

Has anyone else seen this error? (Well, yes, there are lots of people
_asking_ the question but no one ever replies with an answer).

I find that difficult to believe.

 

[Thomas Wildgruber]

No. The error you cite is one that's being generated by the ISP. Either
they have a limit, or - more likely - one of the email addresses in the
list has a syntax error. A space or a comma or some other illegal
character. Start pouring through the address list and find the one that
is wrong. Maybe break the mailing up into multiple batches until you
find one that is broken.

Good idea but this particular address should be displayed in the NDR.
Without the exact error message it's a blind guesswork to debug the
problem.

Bye Tom

 

[imikejackson]

Is it *every time* they create an email with more than one recipient,
or just this particular recipient list for the announcement?


No. The error you cite is one that's being generated by the ISP. Either
they have a limit, or - more likely - one of the email addresses in the
list has a syntax error. A space or a comma or some other illegal
character. Start pouring through the address list and find the one that
is wrong. Maybe break the mailing up into multiple batches until you
find one that is broken.


I find that difficult to believe.

Finally found the offending address card. My guess is that something got corrupted in the upgrade from Entourage X to Entourage 2008 because the only characters showing in the email address are a-z and the "@" symbol.

Also is there a way to tell Entourage to ignore past emails and only suggest addresses from her address book? What happens now is that when she creates a new email and starts typing the individuals name Entourage must find the old "Bad" email from previous and puts that into the "To:" Field instead of getting the corrected one from the address book.

Thanks all for the help.
Mike Jackson

 

[Adam Bailey]

Also is there a way to tell Entourage to ignore past emails and only suggest
addresses from her address book?

http://www.entourage.mvps.org/glossary/mru.html