Exchange 2007, duplicate emails to outside contacts

55 pts.
Tags:
Distribution Lists
Duplicate emails
Exchange 2007
Exchange 2007 administration
External contacts
Setup: MS Windows Server 2003 (domain controller) Exchange Server 2007 Both hosted on the same machine, we only have 1 server. Several internal (on Exchange server) email accounts and several external (SMTP) contacts. Some users (and contacts) are members of multiple security groups. Each group is a member of a megagroup called "Staff". Charles is a member of Leadership, Membership, and Skills. Jennifer is a member of Business, Outside, and Recruitment. Each group is a member of Staff. If I send an email to Staff, Exchange server should break it down to the invidual emails and elimate duplicates. It does this for mailboxes hosted on the server, but external emails receive duplicates (randomly from 2 to 4 copies). As an example: 1) Staff email would be broken down as 2) Business, Leadership, Membership, Outside, Recruitment, and Skills. Further broken down as 3) Jennifer, Charles, Charles, Jennifer, Jennifer, Charles. Which should result finally in email to 4) Jennifer, Charles. Instead step 3 winds up at step 4 as 4) Jennifer, Charles, Jennifer, Jennifer If I send an email directly to Jennifer, she only gets it once. If I send an email to Business and Outside, Jennifer only gets it once. It seems as though the Exchange server is only breaking down external contacts once rather than all the way to individuals (which it does do for internal emails). As an aside, I did install and uninstall the SMTP role on the Windows Server 2003 after Exchange was installed. I read somewhere doing this would break the SMTP for Exchange and require the running of SMTPReinstall.exe to fix. This pointed to earlier versions than 2007 though, and it doesn't seem to apply any longer. Further I can't check the Exchange CD because I don't have one. We needed to get an Exchange server up now, so we opted for the 2007 demo until we could aquire a volume license from our vendor. We're a government office and it'll take a couple of months for the paperwork. If anyone can give me any help on this matter, I would really appreciate it.
ASKED: May 6, 2009  9:47 AM
UPDATED: May 13, 2009  4:28 PM

Answer Wiki

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Hi,

It is possible you have overlapped secuirty groups in a way that cuases this issue. I would recommend distribution groups for easier user managment instead.

Otherwise, the only way to avoid this when using external mail addresses for existing AD members is to add the external addresses in their AD Properties on the Email Addresses tab. If you have mail forwarding set up or Mail Enabled Contacts instead you will see duplicates, since Exchange will resolve addresses for each security group and each mail address as a separate request.

hope that helps,

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  • FreakyFerret
    Hi Carl, I really think this is a "bug" of some sort. I have security groups setup for access control on the network. I based the groups on departments, but some users are members of multiple departments. I then enabled each security group in Exchange as a distribution group (may have the exact term wrong as I'm not near the server right now, just set it so each security group could receive mail and then it sends a copy to each member of the group). Since we have Public users and Staff users, I created a Staff security group which includes all the department goups. This enables easiest management of users, groups, and resources. Some staff members are not users on our domain since they work for a different organization and use that org's network, however they do work in our building and are considered equal staff (they just have no access to our resources). To allow security groups to be used for email distribution rather than having to maintain a totally seperate list of users, I created contacts for these other people. I then assigned these contacts to the security group they belong to. As such I cannot list their external email on an AD user object. So I have AD user objects with Exchange mailboxes and AD contact objects with external email addresses defined. I have multiple security groups consisting of both types of objects. All objects are members of more than one group. There's one supergroup that consists of all the groups as well. If I send email to a user's Exchange mailbox or to the contact's external email, everyone gets only 1 copy. If I send email to one group, everyone gets 1 copy. If I send email to more than one group at a time, Exchange users get 1 copy while external contacts get multiple copies. If I send email to the supergroup, Exchange users get 1 copy while external contacts get multiple copies. (The numbers of copies do not relate to the number of groups an external contact is a member of, the number of copies appears to be random.) Since the Exchange users are not getting duplicates (the Exchange server properly resolves the grouping down to invidividual users), yet the external contacts are getting multiple copies, I think something is wrong with either the Exchange servers resolution system or a setting I set. Any ideas? I don't think setting up a totally seperate distribution grouping as this defeats the purpose of the network/AD layout. Additionally what if I do setup multiple distribution groups, and a user sends email to more than 1 group, the contact would still receive multiple copies. I could be very wrong though, as I've only been using Exchange server for about 2 months and am far from an expert on the matter.
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  • FreakyFerret
    It's the AD Contact entities that are causing the dupes, I'm afraid. Exchange isn't smart enough to figure out tht a user and a Contact are the same even if they have the name name; this is by design. i would disable the AD objects that have the external addys and add the the external emails to the User objects instead; that way Exchange will send one message to each recepient- right now it thinks you have more than one objectwith the same name that needs the message.
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  • FreakyFerret
    Hi Carl, And thanks again for trying to help. You know I've posted this to 5 other tech boards, and you're only one to even try to answer. I really appreciate your help. The AD external contacts do not have an AD user account as well. The contacts have no other AD object referancing them. And actually, if I create an AD user account, give it an Exchange mailbox, create a matching contact, have the mailbox forward to the contact, no duplication. The way I figure it, Exchange resolves the grouping to the 1 mailbox just like the others, then it forwards the email to the contact. Here's a copy of what I posted over at MSExchange.org. I took time trying to be as precise as possible. Maybe it'll help you some more. Setup: Windows Server 2003 Enterprise Exchange Server 2007 AD user objects with Exchange Server mailboxes AD contact objects with external SMTP email addresses Universal security groups. Groups contain both User and Contact objects, with most objects members of multiple groups. Universal security group containing all groups. All groups are made distribution groups in Exchange Server console under Receipient Configuration. Problem: When sending email to groups, Exchange mailbox users get only one copy. External contacts get a random number of multiple copies (usually 2 to 4). The Exchange Server properly resolves invidividual addresses for Exchange mailbox users but not for external contacts. The problem exists regarless of the client used (tested with Outlook 2003, Lotus Notes, Hotmail, and other web-based email clients such as ISP's webmail). No mailbox or contact has forwarding enabled. Not while only one person is given as an example below, this problem exists for all external contacts regardless of which system they are actually on. Duplication occurs for external contacts on Lotus Notes, Hotmail, ISP's email, Yahoo, etc. Example: Charles is a user on the domain with an Exchange Server mailbox. He is a member of the group Management, Summer Workers, and Client Services. Jen is a contact which is a member of Public Services and Business Services. Management, Summer Workers, Client Services, Public Services, and Business Services are members of the group Staff. Use: When sending email to Staff, Charles gets one copy while Jen gets multiple copies. Exchange Server properly changes the email addressed to Staff to its members which are groups Management, Summer Workers, Client Services, Public Services, and Business Services. It then changes those addresses to its members of Charles, Charles, Charles, Jen, and Jen. It then emails to Charles, Jen, and Jen instead of just Charles and Jen. If email is sent to Management, Summer Workers, and Client Services, Exchange resolves those to Charles, Charles, and Charles, and then removes duplication so it finally just sends to Charles. If email is sent to Public Services and Business Services, Exchange resolves those to Jen and Jen but then stops instead of converting it to just Jen. If email is sent to Public Services, then Jen gets only one copy. If email is sent to Business Services, then Jen gets only one copy. If email is sent to Jen's contact, then she gets only one copy. It would seem the problem is simply Exchange Serve is not removing duplicates for external contacts.
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  • FreakyFerret
    Hey, I hope I have your issue straight, happy to help. If I don't type me back and clarify Your issue is because you have these two objects: "AD user objects with Exchange Server mailboxes" "AD contact objects with external SMTP email addresses" Exchange will NOT remove duplicate emails sent to two different types of objects even if they have the same name. so if Jen exists as a AD USer, and Jen exists as a Mail Enabled Contact, Exchange sees 2 Jens, and sends two emails. this will factor by the number of overlapping groups your targets exist in- so if jenExchange and JenExternal are targeted in one group, and you add another higher group that includes JenExternal, she will get 2 mails. add another overlapping group and she gets 4, etc. the best way to add external addresses for an existing user is to add them to the Exchange properties tab on the User properties tab and jettison the Mail Enabled Contacts for those Users- then Exchange will sort out the messages appropriately no matter how many groups are invoked. hope that helps
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  • FreakyFerret
    Hey Carl, Jen does not exist as AD user. She does exist as external contact. She exits only as external contact. She is member of two groups. These two groups are members of a third group (making Jen a member by extention). If mail is sent directly to Jen, she gets 1 copy. If mail is sent to Jen-External-Contact, she gets one copy. If mail is sent to Group1, she gets one copy. If mail is sent to Group1 and Group2, she gets mulitiple copies. If mail is sent to Group3, she gets multiple copies. The number of copies she gets does not relate to the number of groups she's in. It can be anywhere from 2 to 5 copies. I really appreciate you trying to help with this. :)
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  • FreakyFerret
    OK, I get it now. You're sunk. Exchange will not massage Mail Enabled Contacts. it will only send 1 message per request from a container recursively and it will bogie and throw out a few extra depending on how many loops it has to go thru- not QUITE a bug, just less-than-ideal behavior for your needs. It does not treat MEC like Users and there's no way to make it do that. mail tools like GFI can scrub your mail for dupes , but that's an extra layer. making distribution groups is free and easy, so i'd probably create custom distrbution lists for each specific case you have and tweak them as needed; you'll run into this as long as you keep using your current groups as distribution lists. if you have several hundred of these, you're in for a dreary afternoon, but sooner minded sooner mended as they say. :)
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  • FreakyFerret
    Hi Carl, here's a log of a few message trackings. The first list is using mail enabled contacts. Notice how it doesn't remove duplicated ones. The second one is just Exchange mailboxes.
    EventID		Source		SourceContext		MessageID	Receipients			InternalMessageID	ServerHostName	ConnectorID	RecipientStatus							TotalBytes	RecipientCount	RelatedRecipientsAddress	Reference
    Receive		Storedriver				CCBD		SuperGroup			2154			Local MX											6549		1						(null)
    Expand		Routing		Local MX		CCBD		SubGroup1, SubGroup2		2154			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6549		2		SuperGroup			(null)
    Expand		Routing		Local MX		CCBD		User1, User2			2154			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6549		2		Group2				(null)
    Expand		Routing		Local MX		CCBD		User1, User2			2154			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6549		2		Group1				(null)
    Transfer	Routing		ContentConversion	CCBD		User1, User2, User1, User2	2155			Local MX											5126		4						2154
    Transfer	Routing		Resolver		CCBD		User1, User2, User1, User2	2156			Destination MX	SMTP										5170		4						2155
    Send		SMTP		08CB9DeC6F5F86AB	CCBD		User1, User2, User1, User2	2156			Local MX			250 2.1.5 (Users1 and 2 showing up twice) recipient okay	5170		4						
    Submit		StoreDriver	MBD, Event 5620		CCBD 																					(null)		(null)						(null)
    																																					
    																																					
    Just Exchange																																				
    EventID		Source		SourceContext		MessageId	Receipients			InternalMessageId	ServerHostName	ConnectorId	RecipientStatus							TotalBytes	RecipientCount	RelatedRecipientAddress		Reference
    Receive		StoreDriver				CCE9		SuperGroup Z			2851			Local MX											6533		1						(null)
    Expand		Routing		Local MX		CCE9		SubGroup X, SubGroup Y		2851			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6533		2		SuperGroup Z			(null)
    Expand		Routing		Local MX		CCE9		User A, User B			2851			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6533		2		SubGroup Y			(null)
    Expand		Routing		Local MX		CCE9		User A, User B			2851			Local MX			250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded	6533		2		SubGroup X			(null)
    Transfer	Routing		Resolver		CCE9		User A, User B, User A, User B	2852			Local MX											6705		4						2851
    Deliver		StoreDriver				CCE9		User A, User B			2852			Local MX											6705		2						(null)
    Duplicate	StoreDriver				CCE9		User A, User B			2852			Local MX											6705		2						(null)
    Submit		StoreDriver	MBD, Event 10434	CCE9																					(null)		(null)						(null)
    
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  • FreakyFerret
    Okay, the CODE feature on this board doesn't work so well. :/
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