Cannot send mail to mail enabled groups in Outlook 2003 but can in OWA

This is a very bizare situation and I do not know exactly what triggered it. We have Exchange 2003 SP1 in a Windows 2003 AD environment. Our desktop clients are all Outlook 2003.

For some reason, when users try to send to mail enabled groups from Outlook 2003, they don't send. The odd thing about this is that all of the mail in the mail store is set to archive to a specific mailbox. The mail is being sent to the archive mail address but not to the recipiants in the mail enabled group.

However if we send mail through Outlook Web Access, we're able to send to mail enabled groups without any problem.

I'm not sure why this has started happening all of the sudden, but i have tried unsuccessfully to troubleshoot it. I have used Message Tracking but there are no errors other than the fact that when the email comes from outlook it only sends the mail to the archive address but when it comes from OWA it sends it to the email group, splits the message and delivers it locally to all of the members of the group.

I don't understand what the problem could be or what could be causing it.
sjvtechAsked:
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Roshan25Commented:
is this happening for different people doing the same test?
because if this is working in OWA then it's and outlook issue?
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sjvtechAuthor Commented:
Yes it's happening to everyone... however if it's an Outlook issue... what's the issue?
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Rant32Commented:
Hi sjvtech,

- Does it happen on a new distribution list? Try adding yourself to a new DL and send some.
- Does it happen when an Internet recipient sends mail to a DL?
- Are there any application or system Events that have to do with DL expansion or message delivery?

Try creating a separate Address List for distribution groups.
ESM > Recipients > All address lists > Right-click > New address list. Modify criteria to only include mail-enabled groups and QBDL.
Go to the RUS and tell the Enterprise Configuration RUS to update now.
When addressing a message in Outlook, select a DL from this address book.
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sjvtechAuthor Commented:
To answer all of these questions

- Yes this happens with a new group (I have mail enabled security groups, they're not distribution lists). I just made a new one and it still won't send.

- No... suprisingly, when someone from t he outside sends to a group... it makes it through... I have no idea what this means but I just tried it from my yahoo account and the email went through.

- There are no Application or system events documenting this problem... first thing I looked for.

-I created the address list just as described and tried it from Outlook again with no success.

By the way... this doesn't effect Query Based distribution lists... only mail enabled groups.
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kristinawCommented:
it sounds like permissions have gotten goofed up somewhere.

check the security perms on the group and see who has rights to send. perhaps a deny was inadvertently dropped in at a higher level that's propagating down onto all your groups.

kris.

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kristinawCommented:
btw, i'm talking about perms in AD, not Exchange.
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sjvtechAuthor Commented:
No... the group "Authenticated Users" has "Send To" premissions on all groups.

Also I'm a Domain Admin, which has premission to do everything and I can't send either... only extenral addresses and OWA can send and have it go to the individual recipiants.

I wish I knew what the connection was.
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kristinawCommented:
but you did check for deny's right? those take precedence over allows. i'll see what else i can think of in the meantime.

kris.

just out of curiosity, if you create a mail enabled group (not security group, dist group), does that work?
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sjvtechAuthor Commented:
I checked the deny rights... there are no deny rights, I know they take precedence.

Distribution lists don't work either.
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Roshan25Commented:
did you try to send to other mail enable group and are you having the same issue or is it for just for this group....?
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sjvtechAuthor Commented:
No, as I said, it's all mail enabled groups (not query based just regular groups)
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Rant32Commented:
If it were a simple permissions problem then the sender would get an NDR.

What's the scope of the mail-enabled groups? Are you using Global or Universal mail-enabled groups?
Have you recently installed or removed a domain controller or global catalog within the domain?
Have the messages you sent to the groups stalled in the delivery queue on the Exchange server?
Have you tried restarting the Simple Mail Transfer Protocol system service?

Can you troubleshoot this at off-peak hours? If so, it may prove useful to enable maximum diagnostics logging on the MSExchangeTransport components. Then send a message, set back logging levels as they were, and examine the Application log for hints. Don't know what you'd have to be looking for, never seen this kind of black hole behaviour except when groups are empty.
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sjvtechAuthor Commented:
Some good questions... let me give you some answers in case it helps.

Every group is a global Group.

The messages get to the delivery queue, and I see that they get delivered to the archive mailbox, but then they just stop... as if there was no other address to deliver them to. There's no error persay, but when I do the message tracking, there is nothing after the delivery to the archive mailbox.

I've restarted the entire server about 20 times since this problem started.

Now, as far as our domain structure.

We used to have 2 root domains and one child domain.

So it used to be

stjosephsvilla.net (primary root domain)
-------|
         clients.stjosephsvilla.net (child domain of stjosephsvilla.net)

chc.craighealthcenter.net (root domain)

But about a month ago maybe, I removed clients.stjosephsvilla.net (the entire domain). The domain only had one domain controller but it was not a global catalog. Also there were no mail enabled mailboxes in clients.stjosephsvilla.net. It was just an auxilary domain that we decided we didn't need, so I removed it from the forest.

Now we only have our primary root domain stjosephsvilla.net and a second root domain, chc.craighealthcenter.net. Both of which have mail enabled mailboxes and groups.

If this helps you find me a solution then I hope that made since. I will try the diagnostic logging trick as soon as it's off peak hours.

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Rant32Commented:
So if I understand correctly there are 2 sibling domains in the forest?

The recommended setup for mail-enabled groups is Universal Groups, that's very important in a multi-domain setup. Can you try creating a Universal Distribution Group and see if the problem persists?

In which domain do you create the mail-enabled groups?
In which domain does the Exchange server reside in?

Is the Exchange Server a domain controller? If so, it must also be a global catalog.

Open up the properties of the Exchange server computer object in ESM and look at the tab Directory Access. If you use *Global* mail-enabled groups, then the GC that is listed there must be a domain controller in the same domain as where the groups are created. This requirement does not exist with *Universal* groups. Also verify that all domain controllers listed on the DSAccess tab are available. If the Exchange box is also a DC, then it will only list itself as DC/GC.
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sjvtechAuthor Commented:
Rant32 seemed to have the solution... I don't know why but once I changed the global groups to universal groups... all of the groups started working again.

They'd always been global groups, and had always worked in the past (a year). My only guess is that some configuration change or the fact that I dropped my chlld domain or some combination of the two things caused Global Groups to be insufficient even though all of the groups are in the same domain as the mail server and the global catalog.

However, in situations like these, I choose not to wonder why, but be grateful for a solution that allows my users to be happy again.

If anyone does have any further insight on why this may have happened, I'm all ears but thank you for all the help.
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Rant32Commented:
Mail-enabled global groups are listed in the global catalog but *group membership is not*. For Universal Groups, also the group membership is published to the global catalogs. That means that your Exchange server may have been using "empty" global groups for mail delivery.

http://technet2.microsoft.com/WindowsServer/f/?en/Library/0e74916d-28d7-4cdd-8dce-89c824622fcd1033.mspx
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sjvtechAuthor Commented:
OH!

Thank you... my boss is going to want to know the "why" and now I have an answer to the "why"
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Rant32Commented:
Mine never want to know why but only WHEN. One step ahead of 'em this time ;-)

Thanks for the reward.
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