Out of office replies in Exchange 2013 not working for external recipients

Hi,

Few days ago a couple of company workers went to vacation. They set up OOF automatic replies in OWA 2013. However automatic replies are not working for external recipients (outside of company). Internal users (company users) receive OOF notification.

I'm using smart host in sender connector configuration (SMTP server of internet provider) to deliver emails. Any clues about this problem ? Please find below part of the transaction log. For testing purposes i set up administrator account to be on vacation.

HARED... SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
RECEIVE  SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
DROP     ROUTING  Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
AGENT... AGENT    Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
HARED... SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
RECEIVE  SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
AGENT... AGENT    Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
TRANSFER ROUTING  Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
FAIL     SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test

August 6th, 2014 6:45pm

similar article below..

http://social.technet.microsoft.com/Forums/office/en-US/29dc216f-4856-4d09-8245-54e270044937/out-of-office-external-reply-not-work?forum=exchange2010

send connector wont make any issue... can yu confirm if you have already tested this for other domains also... try with some public domains and share results.

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August 6th, 2014 7:03pm

Hi,

Thank you for the reply. I already tested this for dozen of external domains. No success. According to the logs I posted, automatic replies are stuck within exchange. There is FAIL event in logs.

August 6th, 2014 7:51pm

please share the log. or error screen shots.
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August 6th, 2014 8:54pm

Hi,

Please explain what logs are you reffering to ? I already posted part of the Trasaction log for automatic reply message. Do you need any other log ?

There is no error screens. The user from outside of organization do not receive OOF replies and that's it.

Regards

August 7th, 2014 8:09am

Hi Informus,

Please check if it is allowed in AllowedOOFType of the Remote Domain *

In Exchange 2013, the only way to see or change the current configuration for automatic replying and forwarding to the Internet is via the Exchange Management Shell (EMS) with PowerShell commands.

To get the currently configured Remote Domains, use:

Get-RemoteDomain


Name                           DomainName                                   AllowedOOFType
----                           ----------                                   --------------
Default                        *                                            External

Get-RemoteDomain Default | fl AllowedOOFType, AutoReplyEnabled, AutoForwardEnabled

AllowedOOFType     : External
AutoReplyEnabled   : False
AutoForwardEnabled : False

To change the settings, use the Set-RemoteDomain command.

  • Enable automatic replies
    Set-RemoteDomain -AutoReplyEnabled $true
  • Enable automatic forwards
    Set-RemoteDomain AutoForwardEnabled $true
  • Enable OOF for Outlook 2003 and previous (for Exchange 2007 and 2010 support)
    Set-RemoteDomain AllowedOOFType $ExternalLegacy

To change all these properties at once, you can use:

Set-RemoteDomain Default -AutoReplyEnabled $true AutoForwardEnabled $true AllowedOOFType $ExternalLegacy

Note:
Valid settings for the AllowedOOFType property are:

  • External
    This is the default and only allows for the new style OOF messages as introduced in Outlook 2007.
  • ExternalLegacy
    This settings allows for both the new style and old style OOF messages and needs to be set if you want to enable external OOF support for Outlook 2003 as well.
  • None
    This setting doesnt allow for the use of OOF messages at all (both internal and external).
  • InternalLegacy
    This setting only allows for internal OOF messages to be sent for all Outlook versions.
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August 18th, 2014 12:38pm

Hi Satyait

I checked settings for the remote domain. Here are my settings

AllowedOOFType     : External
AutoReplyEnabled   : True
AutoForwardEnabled : True

I do not have Outlook 2003 in organization so AllowedOOFTType set to External should be ok.

Any other ideas ?

August 26th, 2014 5:52pm

Hi Informus,

It could be getting blocked at the External SMTP Gateway server level (Edge).

Please use message tracking to track the OOO message route, this should tell you where its getting dropped and troubeshoot further on that point.

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August 29th, 2014 4:08am

Hi,

I already posted logs from Message tracking log. See my first post. For testing purposes i configured Administrator account to be on vacation. I don't know what other logs you are reffering to ? From these logs i can see tha there is some kind of problem with routing but i can't pinpoint where.

Regards,

HARED... SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
RECEIVE  SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
DROP     ROUTING  Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
AGENT... AGENT    Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
HARED... SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
RECEIVE  SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
AGENT... AGENT    Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
TRANSFER ROUTING  Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test
FAIL     SMTP     Administrator@mydomain.com            {a.b@domain.com}             Automatic reply: vacation test

September 20th, 2014 7:00pm

Hi again,

I checked with my internet provider (i'm using their smart host to deliver mail to external users). They said that auto reply mails are not permitted through their server because return-path field is empty. See link below

http://www.techieshelp.com/exchange-2013-autoreply-replying-external-senders/

Exchange sends out of office replies with empty return-path field by design and this behavior cannot be changed. Since my ISP is not willing allow empty return-path fields is there any other way to solve this problem




  • Edited by Informus Friday, September 26, 2014 12:27 PM
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September 26th, 2014 12:26pm

Hi Informus,

That's sad. But most premium smarthosts (SMTP Gateway) providers supports this (Online as well On-premises).

November 5th, 2014 11:11am

Hi Informus,

That's sad. But most premium smarthosts (SMTP Gateway) providers supports this (Online as well On-prem

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January 4th, 2015 5:27pm

Hi Informus,

Exchange Online Protection is a hosted e-mail security service, owned by Microsoft, that filters spam and removes computer viruses from e-mail messages.

Symantec Brightmail Gateway delivers inbound and outbound messaging security, with effective and accurate real-time antispam and antivirus protection, advanced content filtering, data loss prevention, and email encryption.

This is something extra that most SMTP Gateways provide, apart from just exchanging emails to\fro.

Below are few commercial solutions to name:

0. MS Exchange Server Edge Role (Microsoft)

1. Exchange Online Protection (Microsoft)

2. Websense Email Security (Triniton)

3. Symantec Messaging Gateway appliance \Symantec Messagelabs

4. McAfee also has something similar to offer

January 6th, 2015 8:08am

Hi Informus,

I have a similar problem to yours, did you ever get a resolution to this?

Please post the Exchange shell command you were running to pull the above log data \ event tracking so I can check if the same is happening.

I am running a messag tracking log query which shows my exchange is creating 'Automatic Reply' messages but they are just getting dropped somewhere in the process flow. The only EventId I can see for my messages is two RECEIVE events then the processing stops and no replies are being delivered.

I too am using a smart host to relay mail so want to know if I can indeed approach them with the log data you have produced above.

Many thanks,

durrie.

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September 6th, 2015 1:08pm

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