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Exchange 2007 - out of office replies issue

Posted on 2014-02-11
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Last Modified: 2014-02-12
Hello,

I have a exchange 2007 running on SBS 2008. It is relaying its email to an hMailserver which relays them to Barracuda email secure server (this is how it was required to be build). In this case everything works fine, until I switch on OOF of exchange. They are going fine to the domains setup in hMailserver. However the hmailserver does not allow them to go out, to gmail.com for example.

Here is the log from the hMailserver:

"SMTPD" 1848 675701 "2014-02-11 15:25:03.214" "64.235.151.194" "RECEIVED: MAIL FROM: <testaccount@gmail.com>"
"SMTPD" 1848 675701 "2014-02-11 15:25:03.214" "64.235.151.194" "SENT: 250 OK"
"SMTPD" 3856 675701 "2014-02-11 15:25:03.323" "64.235.151.194" "RECEIVED: RCPT TO: <client@clientdomainname.com>"
"SMTPD" 3856 675701 "2014-02-11 15:25:03.323" "64.235.151.194" "SENT: 250 OK"
"SMTPD" 1940 675701 "2014-02-11 15:25:03.510" "64.235.151.194" "RECEIVED: DATA"
"SMTPD" 1940 675701 "2014-02-11 15:25:03.510" "64.235.151.194" "SENT: 354 OK, send."
"SMTPD" 2964 675701 "2014-02-11 15:25:03.729" "64.235.151.194" "SENT: 250 Queued (0.218 seconds)"
"SMTPD" 3868 675701 "2014-02-11 15:25:03.854" "64.235.151.194" "RECEIVED: QUIT"
"SMTPD" 3868 675701 "2014-02-11 15:25:03.854" "64.235.151.194" "SENT: 221 goodbye"





"SMTPD" 1460 675767 "2014-02-11 15:27:17.546" "81.136.221.242" "RECEIVED: RCPT TO:<testaccount@gmail.com>"
"SMTPD" 1460 675767 "2014-02-11 15:27:17.546" "81.136.221.242" "SENT: 550 Delivery is not allowed to this address."
"SMTPD" 4152 675767 "2014-02-11 15:27:17.577" "81.136.221.242" "RECEIVED: QUIT"
"SMTPD" 4152 675767 "2014-02-11 15:27:17.577" "81.136.221.242" "SENT: 221 goodbye"



How do I solve this? Is the exchange 2007 sending the OOFs in different way than a regular email ?
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Question by:goliveuk
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Simon Butler (Sembee) earned 2000 total points
ID: 39850939
Exchange delivers OOTO messages exactly as the RFC says to.
However other mail servers reject them because the sender is blank. I suspect that is what is happening here. One of the other products is rejecting the email. That is something the others need to fix - you cannot "correct" Exchange, because Exchange is doing it properly.

Simon.
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Author Comment

by:goliveuk
ID: 39852885
Hello Simon,


Thank you for your help. It gave me a start and this is now fixed. In hMailserver a new iprange shoul be created that allow only the exchange to send without auth and it is working fine now.
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