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Outlook 2010 - Send on Behalf only works when selecting senders from the Global Address List...Why doesn't it work when sending from AutoComplete that was from the GAL?

I've followed the steps exactly for setting Delegate access in Outlook 2010 (Send on Behalf access was set up from Outlook, not the Server). The users cannot ‘Send on Behalf’ unless they select the sender’s name from the Global Address List. They have to click 'From' and then click 'Other Email Address...' to go to the GAL. If you try sending on behalf by selecting a name in the ‘From’ drop down box (because it was already sent form that address) it will fail with a non-deliverable error message. This even fails if the name is originally from the GAL. Our organization is using Exchange Server 2007 SP3 and the Domain Controllers are Windows Server 2008 R2 (Server 2003 Forrest Functional Level). All of the affected users with the Send on Behalf problem are using Outlook 2010. Would upgrading Office to SP1 or migrating to Exchange Server 2010 SP1 resolve this issue?
Perhaps on a related note; when adding a contact to Outlook from the Global Address Book, it will disappear from Outlook Contacts after about 10-15 seconds after clicking Save & Close to add it to the Contacts. The work around I found was to click File, Save-As, and save the VCF to my documents then double click the VCF file to add it to Outlook Contacts that way it doesn't disappear. Any help would be appreciated. Thanks. Please Advise.
1 Solution
Jamie McKillopIT ManagerCommented:

In order the use Send on Behalf, the from field must contain the object resolved to the GAL. You cannot simply use the SMTP address as your screenshot shows. You can type the SMTP address instead of choosing the object from the GAL but you must press Alt+K to resovle the SMTP address to the GAL before sending.

USOEAuthor Commented:
I understand that the object does need to be resolved from the GAL as that is the only way it works now. My problem is that the additional email address that is shown in the drop drown in the image above was resolved from the GAL and then is is basically a history of previous addresses sent "from" that is shown. Selecting this address (that was previously resolved from GAL) fails every time. When the organization had Outlook 2007 this worked. Now with Outlook 2010 they have to select Other email Address and then type or select a name form the GAL. I even upgraded to Office 2010 SP1 and it still did not correct the issue. Any other ideas?
Jamie McKillopIT ManagerCommented:
If it is in SMTP format, it is not resolved to the GAL. Once it is resolved to the GAL, it will change to the Display Name and be underlined.

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USOEAuthor Commented:
Thanks for the clarification. Therefore, how you do you get the GAL resolved Display Name to show instead of the SMTP address in the From field when composing a new message in Outlook 2010. Outlook 2007 had a blank line that would display the Display name of the sender, but Outlook 2010 displays the senders SMTP email address in the From field. Any suggestions on how to change those settings in Outlook 2010 would be great.
Hendrik WieseInformation Security ManagerCommented:
Try the following:

1. Create a new mail
2. Now type in the email address that you are trying to send from
3. As soon as the auto complete appears and highlights the name hit Delete on your keyboard to delete the current entry.
4. Now close outlook and open it up again.
5. Now create a new mail again
6. Type the first name of the user and press the Ctrl + K buttons on your keyboard
7. This will create a new auto complete entry.
8. Now try to send an email again and see if you still run into the same problem.

Hope this helps!!
I have the same issue and can confirm that Message ID: 36715535 does not resolve the issue.
Without knowing what access you gave the Delegates.
They should have Full access (Editor) Permissions on Calendar and or Mailbox to send on behalf

Alternativley the easiest way to set this up is via Active Directory
Open the AD account you want the users to send on behalf of
Open the Properties and go to Exchange Advanced
Add the user(s) and give the full Mailbox rights

USOEAuthor Commented:
Wow, I can't believe it actually worked and was so simple. Thank you.
This is a non-working solution. It still presents the problem of, once you have selected the user to send from, provided you have the correct permissions to do so, it only ever allows you to send as that user once, and then the cached address in the from list no longer works. The only way to be able to send as that user again is to delete the cached address from the list, and pick it again from the GAL or another contact list. HendrikWiese should not have been given credit for this. It's simply not good enough. His work around is a temporary one, which essentially brings the problem full circle to where it was to begin with.

Bearing in mind this seems to be an Outlook 2010 issue.

So, what else you got as a solution mate?
Did anyone try it with reapplying the full access / sent on behalf rights on the mailbox ?
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