out of office notification not working with external domain

out of office notification not working with external domain


After enable the Auto Reply on Exchange 2013 MailBox i am unable to get "out of office" allert on any external domain.

I already CHeck :

1. Enable automatic replies
Set-RemoteDomain -AutoReplyEnabled $true
Enable automatic forwards
Set-RemoteDomain AutoForwardEnabled $true
Set-RemoteDomain AllowedOOFType $External

2. et-WebServicesVirtualDirectory -Identity "Server\EWS (Default Web Site)" -InternalURL -ExternalURL -BasicAuthentication:$true
3. Check the SMART host is pointed or not. and found OK rest of the mail communication with External Domain is working fine.
4. Local users are able to receive the "Out of office" notification but issue is with the External DOmain.

Need Help :

1. Find the issue. 
2. Fix this issue.
3. How to find the RCA of this issue.
4. any idea to avoid this issue in future. 

August 11th, 2015 5:56am

Try the below steps

get-mailbox | FL *identity*,*externaloofoptions*
Verify you are allowing replies to remote domains
Almost every  Anti-Virus Mail Scanner has on option to disallow any emails with an empty sender or return path,
So make sure that youre Mail Scanner doesn't block oof messages
If none of the above works then i would suggest you to enable  protocol  logging on send and receive connectors, enable oof for one user , send one test email and see the logs

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August 11th, 2015 9:37am

Hi Sathish,<o:p></o:p>

Thanks for your reply. As per your suggestion I enable oof on a particular mailbox and enable the Protocol logging on send receive connector. And following logs are found.. as per my understanding the return receipt was queued . Can you please go through this logs and analyses...

192.168.33.58 :- Exchange MailBox Server.

192.9.200.17 :- TrendMicro Messaging Gateway.

2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,27,192.168.33.58:7274,192.9.200.17:25,*,,Received certificate
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,28,192.168.33.58:7274,192.9.200.17:25,*,501C95B61B6D39077367ADE577A103E106C912A2,Certificate thumbprint
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,29,192.168.33.58:7274,192.9.200.17:25,>,EHLO ASMSPL-MBX1.doman.com,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,30,192.168.33.58:7274,192.9.200.17:25,<,250-gateway.doman.com,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,31,192.168.33.58:7274,192.9.200.17:25,<,250-PIPELINING,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,32,192.168.33.58:7274,192.9.200.17:25,<,250-SIZE 16777216,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,33,192.168.33.58:7274,192.9.200.17:25,<,250-ETRN,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,34,192.168.33.58:7274,192.9.200.17:25,<,250-ENHANCEDSTATUSCODES,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,35,192.168.33.58:7274,192.9.200.17:25,<,250-8BITMIME,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,36,192.168.33.58:7274,192.9.200.17:25,<,250 DSN,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,37,192.168.33.58:7274,192.9.200.17:25,*,,sending message with RecordId 52286931861750 and InternetMessageId <72ef2f6ab3e348efa42a6a304fdadcde@ASMSPL-MBX1.doman.com>
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,38,192.168.33.58:7274,192.9.200.17:25,>,MAIL FROM:<> SIZE=7552,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,39,192.168.33.58:7274,192.9.200.17:25,>,RCPT TO:<Alex@gmail.com> NOTIFY=NEVER,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,40,192.168.33.58:7274,192.9.200.17:25,<,250 2.1.0 Ok,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,41,192.168.33.58:7274,192.9.200.17:25,<,250 2.1.5 Ok,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,42,192.168.33.58:7274,192.9.200.17:25,>,DATA,
2015-08-12T03:50:21.995Z,Extranal13,08D28B41EAD38432,43,192.168.33.58:7274,192.9.200.17:25,<,354 End data with <CR><LF>.<CR><LF>,
2015-08-12T03:50:22.042Z,Extranal13,08D28B41EAD38432,44,192.168.33.58:7274,192.9.200.17:25,<,250 2.0.0 Ok: queued as 53B5E6E048,
2015-08-12T03:50:22.042Z,Extranal13,08D28B41EAD38432,45,192.168.33.58:7274,192.9.200.17:25,>,QUIT,
2015-08-12T03:50:22.042Z,Extranal13,08D28B41EAD38432,46,192.168.33.58:7274,192.9.200.17:25,<,221 2.0.0 Bye,
2015-08-12T03:50:22.042Z,Extranal13,08D28B41EAD38432,47,192.168.33.58:7274,192.9.200.17:25,-,,Local

<o:p></o:p>

August 12th, 2015 12:06am

Hi 

Your Exchange is working perfectly fine and sending the OOF messages without any issues

Its the Trend Micro GW blocking the OOF messages 

Check your logs in the Trend Micro GW and there should be an option in the advanced settings in the TrendMicro GW to create an exception for these OOF messages

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August 12th, 2015 1:27am

Hi Sathish,

Can you please let me know how to set the Return-Path: <> for a particular Mailbox. In Exchange 2013. 

For your information I Also found that the Mail GW is blocking the Automatic Reply Mails due to mail Sender ID is blank. 

MAIL FROM:<>
August 12th, 2015 1:44am

The return path of any oof messages will be always empty and cannot be modified 

As per RFC 2298 Message Disposition Notification (MDN) messages should be sent with blank sender. The OOF reply messages are an MDN. this is to help prevent looping

some anti-spam products will block sending out messages with blank return path which is in your case

you need to unblock this on Trendmicro which will solve this issue

Free Windows Admin Tool Kit Click here and download it now
August 12th, 2015 3:22am

Hi Koustov,

According to your posting, the configurations in Exchange side should be proper. As what Sathish says, the OOF message may be blocked by the Trend Micro Messaging Gateway.

It is by design that the Return-path of auto-reply for OOF is empty. I suggest we can contact the Trend Micro Messaging Gateway for more help to unblock the OOF message to the external domain. Here is a similar thread for your reference:

https://social.technet.microsoft.com/Forums/office/en-US/341f9a46-53fb-4c27-96b6-0bb9b53d9e23/out-of-office-replies-in-exchange-2013-not-working-for-external-recipients?forum=exchangesvrclients

Re

August 12th, 2015 7:27am

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