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Exchange 2007 on SBS 2008- Delivery delays to distribution groups.

mnsg
mnsg asked
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Recently ran a migration from a 2003 Small Business Server to a 2008 Small Business Server.  The migration has been largely successful, with most compatibility issues resolved in short order.

Noticing something strange regarding distribution groups, however; this was spurred by a number of complaints from end users.

Specifically, if an email is sent to an internal distribution group, the messages aren't actually received by the recipients for 10 to 30 minutes.

If the individual constituents of the distribution group are emailed, the message is received instantly.

The server isn't generating any exchange events at current, the senders are not receiving delivery delay notifications, and the messages are received initially.

I am trying to determine the cause of the delay.  Has anyone seen this behaviour before?
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Top Expert 2010

Commented:
Question
Can you create a new mail enabled distribution group in E2007
Add few users of the previous group.

See if the GAL is populating

Go to Outlook > New Email
Click on TO:> see if your group is listed there.
 
Send a mail out to the group.
See if the users receive it right away

More info.

http://technet.microsoft.com/en-us/library/bb125256(EXCHG.80).aspx

If there are any error codes in eventvwr > application, let us know.

thanks

Author

Commented:
I am able to create and utilize a new distribution group, as well as new mail enabled users.

Created a new distribution group, distrogrouptest and three new users distrogrouptest1, 2, and 3.  Added these three users, as well as my administrative contact (who is in the firmwide group we're having trouble with).

Sent three test messages.
Test 1 was sent to the distribution group.
Test 2 was sent by adding the distribution group, and then expanding it to list its constituents
Test 3 was sent by adding the constituents of the distribution group individually (likely redundant from Test 2, but included for the sake of control and completion).

Test 1 sent at 9:44 AM, received at 9:47 AM, 3 minute delay
Test 2 sent at 9:47 AM, received at 9:52 AM, 5 minute delay
Test 3 sent at 9:48 AM, received at 9:53 AM, 5 minute delay.

No errors in the application log on either client or server.

Interestingly, testing in this manner resulted in quicker receipt of the message by sending to the distro group rather than the individual members- this is completely different from the reported issue, which is still confirmed to be occurring with our firmwide group, with delays of 9-20 minutes today.  Again, sending to the constituent members of the group is is between instant or up to a 5 minute delay.  I'm going to test a few more times with the same settings, as one message with each setting isn't particularly thorough.

Will repost shortly.
Top Expert 2010

Commented:
Thanks for the update. Will wait for it.

Author

Commented:
Did 2 additional tests for each of the previously listed settings;

Tests 4, 7 are repeats of 1.
Tests 5, 8 are repeats of 2.
Tests 6, 9 are repeates of 3.

Sent / received timestamps:
4: 10:08 AM - 10:11 AM [3 minute delay]
5: 10:09 AM - 10:13 AM [4 minute delay]
6: 10:10 AM - 10:15 AM [5 minute delay]
7: 10:12 AM - 10:17 AM [5 minute delay]
8: 10:13 AM - 10:19 AM [6 minute delay]
9: 10:14 AM - 10:20 AM [6 minute delay]

Test times:
1, 4, 7:     Hi: 5 min.  Lo: 3 min.  Av: 3.7 min
2, 5, 8:     Hi: 6 min.  Lo: 4 min.  Av: 5 min
3, 6, 9:     Hi: 6 min.  Lo: 5 min.  Av: 5.3 min

Note that these aren't calculated down to the second so there is a margin of error involved, however it appears that overall the distribution group is quicker than mailing its constituents individually.  This is still opposed to the behaviour seen with the current distribution group.

I've considered recreating the distribution group outright, but the group in question is actually a mail-enabled universal security group that is being used to assign rights to resources as well.  Alternatively, perhaps I could remove the mail settings and rename the existing group, wait for replication, then create a new distribution group with the same name/email address as the old one, then just add the old groups members to the new group?  
Top Expert 2010

Commented:
hi
sorry for not replying here earlier. My apologies

I have a question:
go to Start>Programs > Active Directory Users and Computers

What OU's do you have there.
Specifically my question is - did you migrate any OU's which contains Contacts from SBS 2003 in here.
If yes - go through that OU and see if you can locate the Distribution Group which is causing the delay there.

Next
Go to OU
My Business
distribution groups

Are the newly created distribution groups showing-up here ?
Top Expert 2010

Commented:
hi mnsg
let me know if the issue is still open. Please post back any updates.

thanks
Commented:
Outlook web services were causing Vipre Email Security to Hang which was causing the delay in delivery. This is now resolved