Exchange 2007 - Out of Office Assistant wont send External ???
Hi all, I'm Stuck!!!!! (and yes, i have looked through the forum at similar posts, but to no avail...) I have: Win2008 / Exchange 2007 / external Smart Host for our SMTP mail... Using Outlook 2007 / Outlook Web Access Only come to light now (although always worked in the past), our 'Out of Office' replies arn't sending external... The internal reply works fine, but no external :( Nothing has changed on our server, and just in case something had stopped working, rebooted the box last night, but still no External bound 'OOO' replies.... I'm not sure where to look or what to check, and no reply from the tech support of our mail host just yet... Just trying to see if it is something i could have done, or........... Could it be our SMart Host ? (it uses a Barracuda system)... Could the smart host have accidently created a rule which blocks our outbound 'Out of Office' replies, treating as spam maybe ? etc ? Am stuck!!!!
April 20th, 2012 4:50am

Not unusal for a smart host to do this and the sender address is probably what it is expecting. Check messaging tracking to see where the message goes? Check Remote Domains in the EMC>Org Config>Hub Trans to ensure OOO is allowed? If it's being sent and you can see this via MT , then check to see what happens on the smarthost. Sukh
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April 20th, 2012 6:10am

Not unusal for a smart host to do this and the sender address is probably what it is expecting. Check messaging tracking to see where the message goes? Check Remote Domains in the EMC>Org Config>Hub Trans to ensure OOO is allowed? If it's being sent and you can see this via MT , then check to see what happens on the smarthost. Sukh
April 20th, 2012 6:10am

OOO is set... out of the 4 options in 'Default' under Hub Trans, option 3 is selected... (allow external OOO from outlook 2003 and earlier, etc) As said, used to work, but only noticed now recently its not working.... So my guess is our mail smart host has messed up, but as the guy doesnt answer my emails and i cant check anything on the smart host, guess i am nailed until i hear back from the guy ?!
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April 20th, 2012 8:04am

OOO is set... out of the 4 options in 'Default' under Hub Trans, option 3 is selected... (allow external OOO from outlook 2003 and earlier, etc) As said, used to work, but only noticed now recently its not working.... So my guess is our mail smart host has messed up, but as the guy doesnt answer my emails and i cant check anything on the smart host, guess i am nailed until i hear back from the guy ?!
April 20th, 2012 8:04am

You are, as mentioned use MT, and you can check the send connector logs to see if the message was handed off to the smarthost. Or you can use NetMon to see this is realtime.Sukh
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April 20th, 2012 10:31am

You are, as mentioned use MT, and you can check the send connector logs to see if the message was handed off to the smarthost. Or you can use NetMon to see this is realtime.Sukh
April 20th, 2012 10:31am

Are all users or just some specific user encounter this issue? And, are all external could not receive the OOF message or just some specific external recipient? Just double confirm, please let the problematic user log into OWA, click Tools->Out of Office Assistant. Make sure we enabled the Send Out of Office auto-replies to External Senders option and Send Out of Office auto-replies to anyone outside my organization option. After that, try to send from, say, Hotmail, to the problematic user to see if the issue reoccurs. Thanks. Fiona Liao TechNet Community Support
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April 23rd, 2012 4:50am

Are all users or just some specific user encounter this issue? And, are all external could not receive the OOF message or just some specific external recipient? Just double confirm, please let the problematic user log into OWA, click Tools->Out of Office Assistant. Make sure we enabled the Send Out of Office auto-replies to External Senders option and Send Out of Office auto-replies to anyone outside my organization option. After that, try to send from, say, Hotmail, to the problematic user to see if the issue reoccurs. Thanks. Fiona Liao TechNet Community Support
April 23rd, 2012 4:50am

Its not 1 user, its all Users! (have 50 users, and all 50 of us cant do the OOO!) Whether using the Outlook 2007 client, or by using Outlook Web Access and setting the 'Out of Office' to anyone (including outside my Organization), it still fails to work.... I'm not sure what else to check, or how to check the Out of Office message leaves my mail server on route to my external Smart host (which would then go to the original sender)
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May 9th, 2012 7:27am

have you checked message tracking yet?Sukh
May 9th, 2012 8:01am

have you checked message tracking yet?Sukh
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May 9th, 2012 8:01am

message tracking doesnt show anything... Message tracking shows the message received..... but when looking at the 'SENT' queue, shows no messages going out for OOO auto replies.......
May 9th, 2012 10:55am

message tracking doesnt show anything... Message tracking shows the message received..... but when looking at the 'SENT' queue, shows no messages going out for OOO auto replies.......
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May 9th, 2012 10:55am

Do the connector logs show anything? Any tracking on the smarthost to see if the message was received?Sukh
May 9th, 2012 11:02am

Do the connector logs show anything? Any tracking on the smarthost to see if the message was received?Sukh
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May 9th, 2012 11:02am

to be honest, not sure how to query the smarthost (and whether i would have access) looking at the connector logs now...
May 9th, 2012 11:18am

to be honest, not sure how to query the smarthost (and whether i would have access) looking at the connector logs now...
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May 9th, 2012 11:18am

Been doing some testing.... (as said, this relates to all mailboxes, not just 1). I send an email from my HOTMAIL account to my works email (works email passes through a SMARTHOST first) I receive the email OK, but even with 'Out of Office' turned on, my Hotmail does not receive a reply to say 'I am out'. Using 'Message Tracking' tool in exch 2007, i am seeing this in the Logs.... ***** 2012-05-16T11:19:16.442Z, 192.168.16.2, AIRVENT, <my smarthost IP>, ,08CEEC660082124A, <my server>, SMTP, FAIL, 31883,<<a href="mailto:4F8AE10E97197747BBAFCA4148E1E23369536356224@My server.domain.name>,mymymymymymy@hotmail.com, 550">4F8AE10E97197747BBAFCA4148E1E23369536356224@My server.domain.name>,mymymymymymy@hotmail.com, 550 Empty envelope senders not allowed, 1299,1, ,, Out of Office: newtest3, <my company email name>,<>, ****** So i guess my clue is in the ""550 Empty envelope senders not allowed"", which i guess my SmartHost has a setting which is messing this up ?
May 16th, 2012 7:39am

It's the smart host which will be dropping this, if you do a search here on technet there was a similar post I dealt with, because OofO is sent with no sender the smart host wont allow this through unless an exception is created (a rule) which depends on the smart hosts used.Sukh
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May 16th, 2012 7:51am

It's the smart host which will be dropping this, if you do a search here on technet there was a similar post I dealt with, because OofO is sent with no sender the smart host wont allow this through unless an exception is created (a rule) which depends on the smart hosts used.Sukh
May 16th, 2012 7:59am

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