Autoresponder Not Working in OL2010 + Exchange 2010

It's real simple: send email to, and the auto responder does not respond.

I have already:
Set-RemoteDomain -AutoReplyEnabled $true

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Set-RemoteDomain –AutoForwardEnabled $true

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The user's automatic replies are already set as follows:

[x] Send automatic replies
[x] Send automatic reply messages to External Senders

And messages are set for both.

The user set these up in Outlook, and I confirmed the server "sees" it by checking through the OWA interface under options.

What am I missing here?
LVL 32
Who is Participating?
If these are out-of-office replies, they are classed differently. They are not "automatic replies" so turning that on has no effect.

You need to use
Set-RemoteDomain "Remote Domain Name" -AllowedOOFType External

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You can also turn off the two you've already enabled.

See for more details of the commands.

DrDamnitAuthor Commented:
Doesn't seem to help.

Here are the settings for all domains ("*"):

RunspaceId                           : a8406786-70b9-46f5-bb67-06371aa8d142
DomainName                           : *
IsInternal                           : False
TargetDeliveryDomain                 : False
ByteEncoderTypeFor7BitCharsets       : Undefined
CharacterSet                         : iso-8859-1
NonMimeCharacterSet                  : iso-8859-1
AllowedOOFType                       : External
AutoReplyEnabled                     : True
AutoForwardEnabled                   : True
DeliveryReportEnabled                : False
NDREnabled                           : True
MeetingForwardNotificationEnabled    : False
ContentType                          : MimeHtmlText
DisplaySenderName                    : True
PreferredInternetCodePageForShiftJis : Undefined
RequiredCharsetCoverage              :
TNEFEnabled                          :
LineWrapSize                         : unlimited
TrustedMailOutboundEnabled           : False
TrustedMailInboundEnabled            : False
IsCoexistenceDomain                  : False
UseSimpleDisplayName                 : False
NDRDiagnosticInfoEnabled             : True
AdminDisplayName                     :
ExchangeVersion                      : 0.1 (8.0.535.0)
Name                                 : Default
DistinguishedName                    : CN=Default,CN=Internet Message Formats,CN=Global Settings,CN=First Organization,
                                       CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=mydomain,DC=local
Identity                             : Default
Guid                                 : f75709fa-b0b1-47ed-8f00-567e631dd8e5
ObjectCategory                       : mydomain.local/Configuration/Schema/ms-Exch-Domain-Content-Config
ObjectClass                          : {top, msExchDomainContentConfig}
WhenChanged                          : 10/24/2013 10:48:35 PM
WhenCreated                          : 8/19/2013 1:24:55 PM
WhenChangedUTC                       : 10/25/2013 2:48:35 AM
WhenCreatedUTC                       : 8/19/2013 5:24:55 PM
OrganizationId                       :
OriginatingServer                    : Server01.mydomain.local
IsValid                              : True

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All the users are experiencing the problem. The two that I have been testing with are:

RunspaceId       : a8406786-70b9-46f5-bb67-06371aa8d142
AutoReplyState   : Enabled
EndTime          : 10/25/2013 11:00:00 PM
ExternalAudience : All
StartTime        : 10/24/2013 11:00:00 PM
MailboxOwnerId   : mydomain.local/mydomainOffice/john
Identity         : mydomain.local/mydomainOffice/john
IsValid          : True

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RunspaceId       : a8406786-70b9-46f5-bb67-06371aa8d142
AutoReplyState   : Enabled
EndTime          : 10/25/2013 11:00:00 PM
ExternalAudience : All
StartTime        : 10/24/2013 11:00:00 PM
MailboxOwnerId   : mydomain.local/mydomainOffice/ava
Identity         : mydomain.local/mydomainOffice/ava
IsValid          : True

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The only other symptom I have is when you try to turn off the OOF in John's account via the webinterface, Exchange tells you: "Sorry we can't do this right now. Try again later."
DrDamnitAuthor Commented:
Of course, it is noteworthy that you'll only get one email autoresponse per person per day. So, I have been testing with multiple accounts via
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Glen KnightCommented:
It's probably worth finding out what it is you are trying to achieve.
Your original question tells us what you have done but not what the end goal is.
DrDamnitAuthor Commented:

The goal I am trying to achieve is to have Exchange send automatic replies when the automatic replies feature is set by the user.
Glen KnightCommented:
And just to confirm, we are talking about Out of Office Automatic Replies?  When you go to Outlook

This is sent once per sender until the Out of Office is disabled and re-enabled.

You are saying this does not work?
Glen KnightCommented:
Just reading through the whole thread properly (AGAIN!) :)

Can you disable the Out of Office within outlook client.  Close Outlook.
Then open OWA.  Confirm the Out of Office is disabled and try re-enabling it.

Please post any errors you receive when doing this.
DrDamnitAuthor Commented:
Yes, enable and disable from Outlook does properly show up when I run the power shell scripts. I can see that outlook enables and disables it properly, and it is reflected in OWA as well as EMS. Changing it in EMS is also reflected in OWA and Outlook. Changing it in OWA is reflected in EMS and  Outlook.
Glen KnightCommented:
You said in an earlier post that you received an error when changing it in one location and then trying to change it in another.  Is this not the case now?

Can you explain the Exchange setup for me?

Hub Transport role.  Is there any 3rd party applications installed here?

Do we go from here direct to the internet? Is there an Edge Transport server involved? Firewall? If so which? 3rd party filtering?
DrDamnitAuthor Commented:
I think that error was probably related to a temporary network condition. IT does not happen anymore (I just checked).

The exchange setup is very simple. Windows Server 2012 as a DC, Windows Server 2012 + Exchange 2010 as the Exhange box. This was an "upgrade" from SBS2008. As you probably know, there is no 'upgrade path' from SBS to non-SBS layouts. Thus, we had to export all the mailboxes using the ridiculous 32-bit management machine / 64-bit exchange layout to get the users to PST files so they could be imported into 2012/2010 (Win/Exchange).

This background is useful to know in that there should be no "funny business" that happened as the result of an upgrade. The Server install is new / from scratch. The Exchange install is new / from scratch. We created the users from a powershell script, and imported the mailboxes via powershell.

In hub transport is a 3rd party spam filter:

[PS] C:\Windows\system32>get-transportagent

Identity                                           Enabled         Priority
--------                                           -------         --------
Transport Rule Agent                               True            1
Text Messaging Routing Agent                       True            2
Text Messaging Delivery Agent                      True            3
Connection Filtering Agent                         True            4
Content Filter Agent                               True            5
Sender Id Agent                                    True            6
Sender Filter Agent                                True            7
Recipient Filter Agent                             True            8
Protocol Analysis Agent                            True            9
Vamsoft ORF SMTP Receive Agent                     True            10
Vamsoft ORF Routing Agent                          True            11

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We are routing directly to the internet. No smarthosts or silly ISP mailservers involved.

No Edge Transport (no edge subscription).

There is a firewall, but I am not sure that is relevent in this setup because it does not filter mail / content. It's a custom built M0n0wall. ( The firewall only filters IP addresses and ports.
DrDamnitAuthor Commented:
The only other rules I have are these:

[PS] C:\Windows\system32>Get-TransportRule

Name                                               State    Priority Comments
----                                               -----    -------- --------
Spamify .pw domains                                Enabled  0        Causes emails from domains with the .pw TLD to ...
Spamify .us domains                                Enabled  1
Spamify .me domains                                Enabled  2
SPAM Stamp                                         Enabled  3

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Which sets the SCL level to 9 if the sending domain is a .pw, .me, or .us TLD. The last one sets the SCL to 9 if the subject contains "[SPAM]"
DrDamnitAuthor Commented:
Was that what you were looking for? Or do you need more information?
Glen KnightCommented:
There is no inplace upgrade path as you say, but there is a migration path.  But that's neither here nor there.

When you test the out of office does it work for internal users? So when you turn it on and send that mailbox an email do you get the automatic response?
Glen KnightCommented:
I'd be interested to know the answer to the above.

Could you also run the following commands from the Exchange Management Console:

Get-AutoDiscoverVirtualDirectory | fl identity, *url

And post the results.

My guess is that this hasn't been configured.
DrDamnitAuthor Commented:
Some change we made ultimately fixed it, but I don't know which one. It just started working after I left it alone for a day because I had to attend to other matters (and the person who was out of the office finally came back to work).
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