Exchange 2003 and Outlook 2003 sending issues when selecting a from address

OS: Windows 2003 SBS
Mail Server: Exchange 2003 SBS
Mail Client: Outlook 2003

Mail Server has been set up to receive mail for two domain names. Mail is received just fine from internet for both domains, and makes it into the mailboxes of the respective users.

User accounts have a mailbox with a primary address for the primary recipient domain, and an alias address for the secondary recipient domain. Email sent to these addresses from the internet make it into the clients' mailboxes without problem.

When the users try to send mail, using the From field, and select either their primary domain address or the alias address for the secondary domain, they get an error message like the following:

Your message did not reach some or all of the intended recipients.

      Subject:  example

      Sent:     10/17/2007 9:51 AM


The following recipient(s) could not be reached:

      Someone at another company on 10/17/2007 9:51 AM

            You do not have permission to send to this recipient.  For assistance, contact your system administrator.

            MSEXCH:MSExchangeIS:/DC=local/DC=domainname:servername


However, if they do not choose a From address, thereby simply using the mailbox default address, the message is accepted by the server, and is delivered just fine.

We have installed Exchange 2003 SP2 on the Exchange 2003 server, and have peformed an Office Update on the clients. What could be the cause of this problem? It seems like an Outlook Client problem, but I can't be sure.
kichaneyAsked:
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
I'm not sure what you mean by the fact that you set up an "alias address" for the secondary recipient domain.  Do you mean that you manually added an additional SMTP address to each user's AD Account?  That's not the way you should do this.

Instead, follow this guide for adding the additional domain via recipient policy:
http://sbs.seandaniel.com/2004/10/hosting-multiple-domains-on-sbs-2003.html

Then to allow them to choose which domain to send from, you actually have to use a trick by creating a dummy POP3 account.  See http://sbsurl.com/dummy for a video-how-to.

Jeff
TechSoEasy
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kichaneyAuthor Commented:
No. Actually, the recipient policy was created first, then the Exchange mailboxes created for each user.

A little history might be useful...

The Windows 2003 SBS server was installed initially, and Exchange 2003 installed with it, but Exchange was not needed at teh time of install. therefore when each user was set up, no mailbox was created.

It is now about a year after the server was installed, and a local mail server is now disired. So we set up the recipient policies for two external domains, and then when into ADU&C and did an Exchange task to create a mailbox for each user account. The main default address and alias addresses were thus created automatically.
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kristinawCommented:
normally, when you select 'from', and type in any address associated with your own account, outlook will resolve the name, and your resolved name will appear underlined in the from field. also, you can only respond 'from' your own primary smtp address. so if you have a secondary proxyaddress of me@domainb.com, and your primary is me@domaina.com (the 'reply to' address), if you select from me@domainb.com, your message will still appear to be 'from' me@domaina.com. i guess in this example i'm not sure why they'd be trying to select 'from' anyway, unless there's something we're missing.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Actually it sounds as though you never ran the Configure Email and Internet Connection Wizard (CEICW - linked as "Connect to the Internet" in the Server Management Console's To-Do List).

That would be the first step in configuring Exchange on an SBS.  Then, to add a mailbox to each already created user account you would run the Change User Permissions Wizard to make sure that not only are the mailboxes created correctly, but the users will then be added to the companywide distribution group automatically.

Once that's done, then you can add the additional domain to the Recipient Policy.

The Dummy POP3 Account would still be needed to send from any email address other than the PRIMARY SMTP.

Jeff
TechSoEasy
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
"i'm not sure why they'd be trying to select 'from' anyway"

Because in small businesses, users often wear many hats... and sometimes need to send an email from a different "company" than their primary SMTP address.  This is quite common with smaller companies.

Jeff
TechSoEasy
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kichaneyAuthor Commented:
TechSoEasy said:
"Actually it sounds as though you never ran the Configure Email and Internet Connection Wizard (CEICW - linked as "Connect to the Internet" in the Server Management Console's To-Do List).

That would be the first step in configuring Exchange on an SBS.  Then, to add a mailbox to each already created user account you would run the Change User Permissions Wizard to make sure that not only are the mailboxes created correctly, but the users will then be added to the companywide distribution group automatically.

Once that's done, then you can add the additional domain to the Recipient Policy.
"

Okay, how do I get there from here?

Given the fact that I may have tried to do something manually that is provided for in wizards, is it now possible to complete the steps I may have missed manually, or should I just run the wizards now, even though I have already performed some of the steps manually, and perhaps out of order?
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kristinawCommented:
"i'm not sure why they'd be trying to select 'from' anyway"

Because in small businesses, users often wear many hats... and sometimes need to send an email from a different "company" than their primary SMTP address.  This is quite common with smaller companies.

i understand that. what i'm trying to explain, is that in the given scenario, the FROM address in the mail message is STILL going to be displayed as the PRIMARY smtp address, not the secondary. If this is what he's ultimately trying to do, this will not get him there. sounds like he may still have other config issues though.

kris.
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kichaneyAuthor Commented:
Pursuant to KristinaW's concerns, which I considered valid, I have begun the process of creating a separate account the the alternate alias for each user. (This account is for email purposes only.) I have deleted the email alias for the alternate company from the primary login account for each user, created a second account for each user with only one email address, that being for the alternate company, and have sent each an email from the internet to make sure a mailbox is created, which succeeded. I then configure the security settings for the alternate account so that each user's primary account has full permissions over the alternate account, and then set up the user's Outlook client to open a second mailbox, that being the one for their alternate company account. So far so good.

However, I've run into a snag...

When I click on the alternate mailbox, I get an error stating that the contents can not be displayed. Any help you can provide would be greatly appreciated.

Thanks.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
I'm telling you that you DON'T need to do that... if you follow my suggestion to configure a DUMMY POP3 account in Outlook this will work!  I've done this a ton of times... why haven't you even tried this?

Jeff
TechSoEasy
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
FYI, with the dummy POP3 account the FROM address will NOT be the primary SMTP address, but rather the alternate address that you configure the dummy POP3 account with.

Jeff
TechSoEasy
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kichaneyAuthor Commented:
Okay, found the solution...

I went into the user account properties\Exchange Advanced\Mailbox Rights of the alternate company account and added the primary user account with full privileges. This let me open the mailbox in Outlook while logged in as the primary user. I had tried only going into the User Acount Security properties previously.

Thanks for your input Jeff, but as it turns out, the VP likes this setup better anyway, as the mail goes into two different mailboxes. Your idea about a dummy pop3 mailbox seems interesting though. Maybe I'll use it in the future.

Thanks to both of you. Your input was very helpful.

Kind Regards,

Kent
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kichaneyAuthor Commented:
Well, I spoke too soon...

While the primary user can open the alternate mailbox, and reply to any messages sent to that mailbox as the alternate user, the primary user can not send any "new" messages as the alternate user. I get the same error message as originally reported.

Strange that I can reply to messages sent to the alternate user as the alternate user, but I can't initiate any new messages as the alternate user.

Must I give the alternate user account full access to the primary user account as well? Might this be an issue where the sent message from the alternate account is being written to the Outbox and Sent Items box of the primary user?

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kichaneyAuthor Commented:
"Must I give the alternate user account full access to the primary user account as well? Might this be an issue where the sent message from the alternate account is being written to the Outbox and Sent Items box of the primary user?"

Tried this, and it didn't make a difference. Any help would be nuch appreciated.
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kristinawCommented:
fyi, full mailbox permissions does not also grant send-as. this must be granted explicitly. go back into the user account properties and look for the send-as permission.

kris.
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kichaneyAuthor Commented:
"fyi, full mailbox permissions does not also grant send-as. this must be granted explicitly. go back into the user account properties and look for the send-as permission."

Yes, I realize this. The User Account Advanced Securty Permissions allow for the Send-As permssion. We have set this option already.
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kichaneyAuthor Commented:
To get around this issue, we're probably going to implement the Dummy POP3 account suggestion from Jeff. However, it would be nice to know why the send-as is not working the way we currently have things configured, so if anyone wants to add a comment, I'd appreciate it.

Thanks,

Kent
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
There are larger problems with creating two mailboxes though...

Licensing:  with a second mailbox you would use a second USER CAL.

Remote Access:  the user can't easily access all of their email via OWA or Outlook Anywhere (RPC over HTTPS).  

Management:  Twice as many mailboxes to manage is not only more work, but creates a greater chance of causing mailbox corruption.  Deleted Item Recovery becomes more complicated as does backup and disaster recovery.

Regarding the problems you encountered... there is a difference between "Send as" and "Send on behalf of" permissions.  http://www.msexchange.org/tutorials/Sending-As.html

Jeff
TechSoEasy
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