Outlook Express - Leopard Server refusing to deliver to non-local recipient

Morning all,
I have a 10.5.6 Server running IMAP / POP / SMTP services.
All Mac Leopard clients are working as expected, delivery to both local and external addresses works as expected.
However, Outlook Express will connect and retrieve mail (POP) but will only send to local recipients, any other addresses are refused delivery.
e.g.
Delivery to [email protected] works for both Mac and Windows.
Delivery to [email protected] work for Mac but not Windows (Outlook Express)
Any help would be appreciated.

Sounds like it is not authenticating correctly. Make sure the authentication methods for SMTP match what you use on the client.
Failing that, increase the logging level for SMTP to "Information". Next, try to send mail and see what the logs show for that timeframe.
Alex

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I found this and it worked for me too....
Outlook 2011 Moving Exchange Messages To On My Computer
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Please post it here as this forum is meant only for Windows server general queries.
http://community.office365.com/en-us/f/156.aspx
http://www.arabitpro.com

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Welcome to *Apple Discussions*!
Outlook Express Mail is not a Mac application. Therefore:
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Hello Keith,
Many thanks for sharing the search reasults for the 0x800CCC0F error.
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Hi
+"Can I set up Snow Leopard Server so that the Outlook 2003 clients will be able to use contacts, calendars and mail etc from the mac (mini) that we would purchase for this?"+
For mail yes. For calendars you will need 'assistance' using 3rd-party applications or helper utilities. The iCal Admin manual has more details of what is available:
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Hi, I use MacOS 9.2.2 and OutLook Express 5.0.6. I have two email accounts. Lately whenever I go to retrieve email on one of the two email accounts, I get the following error description window: "Error: A message in your Outbox could not be sent. The server did not recognize the recipients. Explanation:
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Happy Holidays!!
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Hi BDAqua,
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hi,
i have setup a mail server w/ mac osx snow leopard mac mini, and i have setup the smtp and open relay to spesific IP address.
Now everything looks fine for all the users, except for the users that using outlook express, they can retrieve emails, but can not send.
the error message is like this :
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probably your smtpdhelorestrictions.
In /etc/postfix/main.cf, look for this
smtpdhelorestrictions = _________
If you see this:
smtpdhelorestrictions = rejectinvalid_helohostname rejectnon_fqdn_helohostname
Change it to this:
smtpdhelorestrictions = permit_mynetworks permitsaslauthenticated rejectinvalid_helohostname rejectnon_fqdn_helohostname
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I have just migrtaed from PC to MAC - so be gentle with me...
I have several email pop3 accounts (hotmail, o2, gmail etc) that on my old PC I used via Outlook Express or Live Mail. Obviously all the mail that still sits on the Servers in the Inbox can be down loaded into iMail - I've lreay done this by creating the accounts in iMail and syncing
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see this link for a few methods of transferring your mail from outlook to Mail.
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Hi All,
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Your server has unexpectedly terminated the connection. Possible causes for this include server problems, network problems, or a long period of inactivity. Account: 'pop.cbn.net.id', Server: 'smtps.cbn.net.id', Protocol: SMTP, Port: 587, Secure(SSL): Yes, Error Number: 0x800CCC0F
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Sorry I'm a little late to the party.
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Outlook Express - Leopard Server refusing to deliver to non-local recipient

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