Recipients does not matter. Internal or external, 2003 or 2010. When they send 
on behalf of they get the error every time when selecting from the remembered 
address. It will work when they go through the address book to find the name.

We ended up migrating one of these users and the associated mailbox they send 
on behalf of to 2010 to see if that would resolve the problem and it actually 
got worse.

When running from the 2010 the message is returned undeliverable...

Delivery has failed to these recipients or groups:

Lastname, Firstname
You can't send a message on behalf of this user unless you have permission to 
do so. Please make sure you're sending on behalf of the correct sender, or 
request the necessary permission. If the problem continues, please contact your 
helpdesk.

Diagnostic information for administrators:

Generating server:

/O=GPRC/OU=GPRC/cn=Recipients/cn=username
#MSEXCH:MSExchangeIS:/DC=ca/DC=ab/DC=gprc:SERVER[578:0x000004DC:0x0000001D] #EX#

Does that mean send on behalf needs to be reconfigured after migration?

Thanks,

Matt Thiessen

From: pramatow...@mediageneral.com [mailto:pramatow...@mediageneral.com]
Sent: Thursday, June 02, 2011 9:10 AM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

Don't think deleting other names would help.
Don't think cached mode would make a difference, seems the OAB address works 
it's just the dropdown...

What about the recipients? Any difference in sending to 2003 vs 2010 recipients?
/reaching

From: Thiessen, Matt [mailto:mthies...@gprc.ab.ca]
Sent: Thursday, June 02, 2011 10:18 AM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

Thanks for all the responses. I suppose it is possible that the mixed mode is 
causing problems. I would expect that if we had moved one and not the other. We 
tend to move people to the new server in batches, especially when they have 
permission to each other mailboxes. In this case both are still on exchange 
2003.

I have tried deleting the name out of outlooks quick complete dropdown at the 
from field. I don't think I have tried yet purging all the autocomplete data. 
Would doing that help? I believe that if the profile is deleted and recreated 
it works for a while before breaking again.

Thanks,
Matt

From: pramatow...@mediageneral.com [mailto:pramatow...@mediageneral.com]
Sent: Thursday, June 02, 2011 5:29 AM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

Yeah, I just don't remember if the autocomplete business helped or not.

"...I can say without a doubt you will be much happier when you have finished." 
 <--  QFT:)

Paul

From: Matt Moore [mailto:mattmoore...@hotmail.com]
Sent: Wednesday, June 01, 2011 11:27 PM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

In my roundabout way I guess that was the main thrust of what I was saying.  
Get everyone on same side, shared mailboxes too.  We seem to have the most 
problems like that when there are 2 versions at play.

It does help a lot!

M

From: pramatow...@mediageneral.com [mailto:pramatow...@mediageneral.com]
Sent: Wednesday, June 01, 2011 6:17 PM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

Apologize, because we don't have many "send on behalf of"'s the migration was a 
while back and still have memories of a snakebite or two-
What happens if they
[1]delete the boss's name from autocomplete and send a message (which should 
work)
[2] with autocomplete repopulated, what happens?

Don't know if it would matter but are boss and send on behalf people all on the 
same V of Exchange? FWIW we moved "groups" like that to try and mitigate 
problems, I like to think it helped a little.

From: Matt Moore [mailto:mattmoore...@hotmail.com]
Sent: Wednesday, June 01, 2011 6:53 PM
To: MS-Exchange Admin Issues
Subject: RE: Send on Behalf error

That's pretty typical behavior during a migration.  I've run into that and an 
awful lot of others and they're all different.  My first response would be 
apologize up and down for the inconvenience and get that migration done as soon 
as possible.  Nothing causes friction like a migration, we've had a number of 
clients run into this same scenario and put the brakes on the migration 
temporarily, thinking the problem would follow into 2010.  All have felt the 
pinch of that decision.   Well, hind sight being 20/20 I can say without a 
doubt you will be much happier when you have finished.  I think our smoothest 
migration to date was for 80,000+ users all done in one weekend.  Sure there 
were a few issues but they were all taken care very quickly in comparison.
I guess that wasn't really how to fix it, sorry about that, more looking at the 
bigger picture.  Get it done then track down the problems when you don't have a 
basket of snakes, venomous ones.

M

From: Thiessen, Matt [mailto:mthies...@gprc.ab.ca]
Sent: Wednesday, June 01, 2011 3:17 PM
To: MS-Exchange Admin Issues
Subject: Send on Behalf error

Hello,

I have run into and interesting problem when using outlook 2010 with exchange 
2003. The user has permission to send on behalf of their boss. When they go 
into the from field and look up their boss the email gets sent fine. When they 
select the same from email address using the dropdown where it remembers the 
name the message does not go through. They get a NDR with the following:

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

      Subject:    test
      Sent: 5/24/2011 1:50 PM

The following recipient(s) cannot be reached:

      Lastname, Firstname on 5/24/2011 1:50 PM
            You do not have permission to send to this recipient.  For 
assistance, contact your system administrator.
            MSEXCH:MSExchangeIS:/DC=ca/DC=ab/DC=gprc:servername

I will mention as well that they are running in cache exchange mode on the 
client, it is happening to more than just 1 person as well. We are running in a 
mixed mode environment with users being migrated over to 2010.

Any ideas will be appreciated.

Thank you,

Matt Thiessen
IT Systems Manager
Grande Prairie Regional College
780-539-2852

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