Some users cannot send mail using alias

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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....

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.