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Some users cannot send mail using alias

Posted on 2014-01-03
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Last Modified: 2014-01-28
We are running coexisting Exchange 2007 and Exchange 2013 and in the process of migrating all mailboxes to 2013. I have run into a stumbling block where some users cannot send email from alias while others can. So far the two that cannot have been migrated to 2013. These two use Outlook 2007 via Terminal Server. The users without issue either use Outlook 2010 on stand alone computer, or are still on 2007. What I can figure so far is that the issue can be reproduced using a known working mailbox where sending from an alias has been tested successful by setting it up on the terminal server outlook 2007.
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Question by:sailci
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Expert Comment

by:Will Szymkowski
ID: 39756017
If the user uses OWA to send email do they run into this issue? If you have Exchange 2013 and your clients are using Outlook 2007 then you need to have SP3 and cumulative update from july applied to the machine for full support. Take a look at the link below for all supported version of Outlook for Exchange 2013 and the SP level they need to be at.

•Outlook 2007 SP3 with July 2012 Cumulative Update
http://blogs.technet.com/b/jribeiro/archive/2012/09/25/exchange-2013-preview-supported-outlook-clients.aspx

Will.
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Author Comment

by:sailci
ID: 39760876
Thank you Will. I was certain I verified all of the TS, but I just found thanks to you that I had not. I will be updating one tomorrow and will let you know the outcome.
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Author Comment

by:sailci
ID: 39762630
Didn't realize until after I downloaded, but that is for standalone Outlook. I tried to install it anyway but it threw up error that no compatible products were found. So, I installed Office 2007 SP3 and subsequent updates to no avail. The OWA test won't work as far as I know because you cant choose to send from an alias.

Also, I was just made aware of another Outlook 2007 issue: I had two reports yesterday from users unable to turn off their out of office message within Outlook. It said it was off but the OOO message continue to go out.
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Expert Comment

by:Will Szymkowski
ID: 39762702
I am not sure if this is exactly your issue after reading but take a look at the below link which i beleive outlines what your asking. Let me know if i am correct.

http://social.technet.microsoft.com/Forums/exchange/en-US/8088074b-ec88-4653-87c5-0369d9b3e01d/cannot-send-out-message-with-from-is-alias?forum=exchangesvradmin

Will.
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Author Comment

by:sailci
ID: 39762883
Yes, the error is different but what the user is doing is the same. They have primary email account as Exchange and alias email as POP. Everything worked fine until migrated to 2013. Here is the error my users are getting:

Your message:
   From:    <sender email account address (primary SMTP)>
   Subject: test

Could not be delivered because of

Server refused mail at END OF DATA - 554 5.6.0 Invalid message content

The following recipients were affected:
    recipient's email address


Additional Information
======================
Original Sender:    <senders email account address>
Sender-MTA:         <sender's IP>
Remote-MTA:        <IP of 2007 CAS???> Why would it be going through 2007 CAS after migration.
Reporting-MTA:      <mailmarshal server???> This particular message was internal so not sure why it would touch mailmarshal. But to note, there was no indication that it did according to the admin.
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Expert Comment

by:Will Szymkowski
ID: 39764825
It is possible that you have a routing issue with Exchange. Look at your send/receive connectors and ensure that everything is set properly.

Will.
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Author Comment

by:sailci
ID: 39765750
I checked my send/receive connectors again and I think everything is correct. I have never tried to configure a coexistence scenario so I am not 100% sure. What I did during initial configuration is modified the existing send connector, adding the new server and leaving everything else alone. For the receive connectors I made no changes to the 2007 CAS, and for the 2013 CAS I added in the same connectors (minus the ones auto created by Exchange) and settings as I have for the 2007 CAS.

One thing to note is that when I first tried to reproduce the problem I was unable to from Office 2010 on a stand alone PC. However, when I logged in to the Terminal Server which has Office 2007, the problem was easily reproduced using the same email account and alias.
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LVL 53

Expert Comment

by:Will Szymkowski
ID: 39765860
Did it ever work on the Terminal server Outlook 2007? In Outlook 2010 and 2013 you can create multiple profiles under 1 Exchange Account, you cannot however do this with previous versions. Also does your connection status for Outlook 2007 and Outlook 2010 show the same Exchange servers and authentication servers (DC's)?

Will.
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Author Comment

by:sailci
ID: 39768966
It worked on the Terminal Server with Exchange 2007, and still does for the few users that have not been migrated as far as I can tell. So the way it gets setup for these users is 1 profile with two accounts (1 for Exchange and 1 for POP/SMTP). Exchange account is their primay email address and so far seems to work without a problem. The POP/SMTP account is the alias email address and this is where things get broken somehow after migrating to 2013. When I checked the connection status on the tested and working standalone computer and the non-working Terminal Server, both use the same address for the Proxy and the servers are listed as <guid>@domain.com which match up.
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Author Comment

by:sailci
ID: 39771676
I have now confirmed it has something to do with Terminal Servers. I am only able to install and test Terminial Server of Win2K3 servers, but that is what the production TS are. I installed Office 2007 on a standalone computer and tested and everything works just fine. So I guess what I need to try to understand/figure out is how Exchange 2007 and 2013 differ such that it would create this issue only for Terminal Server users.
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Assisted Solution

by:Will Szymkowski
Will Szymkowski earned 500 total points
ID: 39771711
If you create new accounts on Exchange 2013 does the terminal server method work for you? Or is it just mailboxes that are migrated that fail? Can you compare settings for users that work to users that dont? Are the users all using cached mode or online mode?

Will.
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Author Comment

by:sailci
ID: 39771973
Let me get those answers for you. I am pretty sure the settings being used are the same, when I was creating the Outlook profiles on the TS for my account and for the standalone, I used the default settings. On the TS it was a no go but the standalone was fine. However, I did not specifically look at the settings. I have been using my account as a test account because it is a migrated account and not a new account. I will create a new account in 2013, configure the client on the TS and see what the outcome is. I will double check cached mode as well. I'll be back soon....
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Assisted Solution

by:sailci
sailci earned 0 total points
ID: 39772083
Well, I don't get the why of it, but it has to do with cached exchange mode. I turned it off on the standalone that worked fine and it then presented the same error as the TS. I turned cached mode back on and everything back to working. The account I am using has never been on the TS or this other standalone before so I would not have even thought cached mode would be a factor. I also don't get why only the 2013 migrated users seem to be affected. The good news is the problem is narrowed down a little bit more again.
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Accepted Solution

by:
sailci earned 0 total points
ID: 39804372
I thought I already closed this out. Somehow my notes, etc. did not go through. Anyway, this problem cannot be directly resolved in my case because many cases require Outlook to run in Online mode. One work around is to create a separate profile in Outlook with the dummy POP address. The user can switch to that profile when they need to send from their alias address. However, when the user receives an email sent to the alias it will still go into their Exchange inbox and the user cannot directly reply to it. The only other option is to create a separate mailbox and provide Full + Send As rights. I have used both of these options, which one depended on the user and what it was they needed to do. I no longer recall with 100% certanty, but believe this to be an issue only with Outlook 2007 when running in Online mode, but I may have been able to reproduce it in Outlook 2010 running in Online mode. For reasons unknown to be, exchange cached mode fixed the problem for both versions on Outlook we use.
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Author Closing Comment

by:sailci
ID: 39814557
Because my comments detail the solution I found through troubleshooting. I want Will to get his points though as his questions steared me towards the solution.
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