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Cant send from non primary email for one user

Posted on 2007-10-15
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Last Modified: 2013-12-05
Using a Windows 2000 Domain, Exchange 2000 using Outlook 2003, if I add a new email address, be it for a new domain, sub domain or existing domain, to a one particular user in ADUC and they try to send from it*, they get a NDR, but if I set the new email as the primary email, they can send from it.  
* Only a problem when sending to external email addresses.

The odd thing is that other users can send from secondary emails, albeit for addresses belonging to the same domain.  (I am yet to test with other domains)

In Outlook, if you type in the secondary email address in the From field in Outlook, it doesnt resolve to their AD Contact, where as other users type in their alternate email addresses and it will resolve to their AD contact.  
E.g When you type in a primary or secondary email of an AD user in the From, To or CC fields and click Check names, it will resolve the name.  If the address is attached to an AD user, when you double click on the resolved name, it should open a popup called '<Username> Properties' with 5 tabs if its recognised as an AD user, but if not it will open a popup called 'E-mail Properties' with no tabs.  In my case, its doing the later despite the fact that the email is attached to an AD user.

The NDR is:
"
Your message did not reach some or all of the intended recipients.

      Subject:      Test
      Sent:      15/10/2007 12:06

The following recipient(s) could not be reached:

      user@theirdomain.co.uk on 15/10/2007 12:06
            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            MSEXCH:MSExchangeIS:/DC=UK/DC=CO/DC=OURDOMAIN:EXCHANGE
"
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Question by:FSIFM
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by:cjpalmer
cjpalmer earned 300 total points
ID: 20079263
I may be mistaken, but in my experience, if you are using Outlook and you put an account in the From, it will go out as the primary address for that account, not the secondary address that you typed in to get it to resolve. If you do some tests and look at what address the message is coming from, you will likely see the primary address and not the secondary address is the source.

As to your specific problem with this one user, it might be a synchronization issue. If the AD and GAL aren't fully synced up, you may see it not resolve, but more commonly, it is the local copy of the GAL on the client machine that isn't updated yet and until it updates, it won't. By default, it should update the local GAL copy on a nightly basis. But, you can force it by going to Tools/Send & Receive and selecting Download Address Book.

Charles
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by:FSIFM
ID: 20079501
Thanks for the advice.
In Outlook, you are correct if you type in the display name as this will resolve to the primary email for any account.  The issue I have it when you type in the full email address of a secondary email to that of a given logged on user.

E.g - 'User Lastname' has the following emails assigned to them.
user.lastname@ourdomain.co.uk = Primary
user@ourdomain.co.uk = Secondary
user@sub.ourdomain.co.uk = Secondary
user@newdomaon.co.uk = secondary

In Outlook, I type the full address of a secondary email but it doesnt resolve to 'User Lastname', but instead resolves to a standard email.  When I type in an external To address and click send, it bounces back with from System Administrator saying "You do not have permission..."

I had already explored the GAL option, but my approach was to re-name the Outlook.NK2 that was against the profile, although I also tried your solutions, but unfortunately it didnt work.

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by:cjpalmer
ID: 20079821
If you open up your GAL and find the user and look at them, does it list the secondary address there? Also, the NK2 file is just for the drop down list of what it recommends to you. It is not the Offline Address Book (.OAB I think).

Charles
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by:FSIFM
ID: 20079856
Good question, but I have also checked that and yes all the seconday emails are in there.

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by:cjpalmer
ID: 20079956
Ok, I just tested with an additional email address that is on my account and I am having the same problem. Even though the address is there, I don't know if it looks at the email address. I know it looks at the Exchange Alias looking for a match there, I don't know if it does that further check of every possible email address. That can become a very expensive check. We have more than 10,000 addresses in my environment and if it had to look up each one to resolve it, that might get to be a very big load quickly. The NickName (nk2) file minimizes the looks that need to be done, but still, in a big enough environment, I think that would be a problem.

Is it possible that the contacts have been added to the mailbox of the person sending them so everything is a local lookup? I am thinking NO because when I tested it here, it only added my primary address to the Contacts. It didn't put in the other addresses. I also had a thought about receiving an email as the secondary address maybe adding that reverse lookup functionality and that didn't work for me either.

This is a weird one.

Charles
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by:Sembee
ID: 20082387
You seem to have two issues here.
1. The way that you are trying to use the secondary address isn't going to work.

You cannot select another email address on the same user account in this way.
If you have more than one email address for a user then you need to look at a solution to work with those. That either means a second account or a third party tool such as choose from.

2. Name resolution isn't working correctly.
Does the name resolution work in the To field?

Simon.

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by:FSIFM
ID: 20084066
I added another email for a different domain to another user, and when I typed in the full email in the From field of their Outlook app, it resolved to the users display name.  Cant understand why it doesnt work for my account.  However, I can see that it means that emails will be sent from the Primary address.  

Strange thing, is that for me, I was able to send from secondary addresses in the past, but the last time was either when we routed emails to a SPAM filter server using GFI Mail Essentials via an SMTP connector or prior to a whole load of security patches that we applied.

I am now finding that I cant even send to internal addresses from my secondary account, despite me being a domain admin!

Sembee:  To answer point 2, it doesnt resolve in the To field either

So its likely I had the resolution problem all along, but was previously able to send from secondary emails!!!  I suspect its my issue was that I accidently expoited a loophole in Exchange that was fixed by a security patch.

Any ideas to resolve it though would still be most appreciated, loophole or not.   8-)
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by:Sembee
ID: 20085189
I don't know how you would have been able to send email as a secondary address, because Exchange has never allowed to do that - security patches or no security patches. You may have thought it was going out like that, but would have resolved and gone out as the primary address.
The only way you would have got an email to go out as a secondary would be using POP3/SMTP accounts in Outlook instead of Exchange.

Does the account appear in the GAL? If the account is hidden then Outlook cannot resolve it.

Simon.

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by:FSIFM
ID: 20085803
Yep, the account does appear in the GAL and the email addresses appear in the Email tab of the users properties.

I think a solution to my sending issue is to create a mail enabled security group with the users secondary email and attach the user to that group.

As for the name resolution issue, I will try again after removing some of the secondary emails on the problem account, as I find it strange that one users secondary emails resolve to the display name and one doesnt with the only difference I can see it that the problem one has more secondary emails.
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by:Sembee
ID: 20086745
The usual method for a second address is a second account, not a group.

Simon.

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by:FSIFM
ID: 20086790
I have considered another group, but would that result in emails for the second address going into a separate mailbox?
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Sembee earned 1200 total points
ID: 20087036
Rather than repeat myself, take a look at this page on my web site:  http://www.amset.info/exchange/twodomainsoneuser.asp

Simon.

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