Out of Office replies not working for external emails - Exchange 2010, Outlook 2010

Hello.
We have two Exchange 2010 mailbox servers and a third for client access. There are two mailbox databases replicated to both servers as a DAG. There is also one 2003 legacy server that is awaiting decommissioning that is basically just heating the server
room - all the mailboxes have been migrated.
We have recently noticed that out of office replies are no longer working for external recipients, but are being sent for internal users.
I have checked under "Organisation configuration" - "hub transport" - "Remote domains" and made sure that is set to "Allow external out-of-office messages and legacy out-of-office messages"
Looking at the message tracking logs it appears that the out of office reply isn't generated for external users - we do have an external mail filter that inbound and outbound messages are relayed through but that isn't blocking anything.
This was working until recently, and I can't see any errors in the logs that look related. All three servers have been rebooted just in case.
Any suggestions where to look next?

Hello,
You can capture a trace log to diagnostic
the OOF issue:
a. Start ExTRA by clicking Run on the Start menu and then entering the following command-line:
Extra.exe
b. On the “Welcome to the Exchange Troubleshooting Assistant” page click Select a task. 
c. On the “Troubleshooting Task Selection Screen” page click Trace Control. 
d. Click OK to the following prompt alerting you about possible performance problems running a trace:
This server does not have the module needed for interpreting traces.
Proceed only if this is being done under the direct supervision of a qualified Exchange support engineer.
e. On the “Configure Trace File” page configure the following options:
f. After configuring the options in step e, click Set manual trace tags. 
g. On the “Set Trace Tags Manually” page configure the following settings: 
Check the following trace tags: InfoWorker.Assistants.OOF, all.
Note: Please expand all filter options, make sure that we did not check any filter options here. And run the trace again.
h. Click Start Tracing at the bottom of the page.
i.  Please reproduce this issue for 3-5 times. After reproduced this issue, stop the tracing and collect the ExchangeDebugTraces.etl
Thanks,
Simon

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    Hi!  I have a user on our network that cannot use Out of office or see free/busy information in meeting requests.  We have hundreds of working 2010 clients but this one is 2013 and NOT a member of our domain.  They are connected to exchange
    and can do anything except the above.  When I do a test of email autoconfiguration it just fails.  DNS resolution is working fine but it can't connect to the server for these two functions only.  Any articles I can find assume the user is remote
    and outside the network but he is connected internally.  Any ideas?
    Thanks!

    Hi,
    Please switch to Outlook 2010 client and login OWA to check this issue.
    The Microsoft Exchange Server 2010 Availability service makes free/busy information available to Outlook client. Then Outlook uses the Exchange Server 2010 Autodiscover service to obtain the URL of the Availability service. As you
    mentioned, it failed to do a test of email autoconfiguration. So I suggest the following methods for troubleshooting
    Please switch to Outlook 2010 client and login OWA to check this issue.
    Have you configured
    Autodiscover Service for Internet Access?
    Use Test-OutlookWebServices cmdlet to
    verify that the Autodiscover service settings for Outlook clients are configured correctly.
    Blog for
    reference to troubleshooting Autodiscover.
    Best Regards.
    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected]
    Lynn-Li
    TechNet Community Support

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