BUG - Outlook 2010 'send as' permissions - Workaround within

issue : when a user attempts to 'send as' another mailbox, the email fails with Undeliverable message:
"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 ".
This error only occurs once the email address has been cached (ie: 2nd attempt to 'send as' a user). Permissions are correct as 'send as' worked fine when using outlook 2007. upgrading
a client to outlook 2010 results in the above error.
scope : outlook 2010 clients with exchange 2007/2010 (appears to be client related, not exchange server). windows updates as of 22-dec-2010 have not resolved this.
workaround : Cached Exchange Mode is ENABLED. Disabling this and restarting outlook resolves this issue. (Outlook 2010 > File > Account settings > Account settings... > double click the default account on the 'EMAIL' tab > untick
'used cached exchange mode'.)
i hope this helps other people; i've been googling for a resolution to this issue since beta/RC. now i've got office 2010 RTM the issue was still present. no forums/blogs could
shed light on this issue.
Is this the correct way to report bugs, or is there another way? i've tried connect.microsoft.com, but theres no "accepting bugs" for the outlook/office suite.

Nothing particularly useful in that thread either:
by: busbarPosted on 2010-06-07 at 08:12:05ID: 32933664
1) looks like you have an issue with the DC plesae check it
2) restart the information store and system attendant to speed it.
3) send as is managed using send as permissions in the EMC
http://technet.microsoft.com/en-us/library/bb676368.aspx
by: totallytontoPosted on 2010-06-07 at 08:45:34ID: 32934043
dont amend the settings in active directory for exchange 2010 servers. use the exchange management console> recipient config>mailbox and use 'manage send as permission' in the right pane.
by: SatyaPathakPosted on 2010-06-07 at 11:55:55ID: 32935929
Its looks like permission issue.
Go through .
http://blog.nick.mackechnie.co.nz/post/2009/11/20/Exchange-2010-Active-Sync-Issue.aspx
http://social.technet.microsoft.com/Forums/en/exchange2010/thread/b28ea96a-8458-4ec8-87a8-66f64cbb7600
by: coderccPosted on 2010-06-07 at 19:00:23ID: 32938614
Or bypass it all with a 3rd party app: http;//www.servolutions.com/changesender.htm
by: ExchisaPosted on 2010-06-08 at 01:20:07ID: 32940097
SatyaPathak: :
I already tick the checkbox to inherit all the permissions from the parent , now for those who
are members of any protected group , this check box keep un-ticked  again every 15 min ,
active directory keep synchronize these permissions with adminsdholder .
anyway my problem are still open , hope it solved .
wait something
by: totallytontoPosted on 2010-06-08 at 04:28:40ID: 32940992
Hi Exchisa,
Many, many apologies, as I mis-read your query and missed the vital bit of info (serves me right for reading it on my mobile...)
I'm afraid you are a bit stuck. Members of the protected groups are automatically reset to the approved permissions at regular intervals as a security measure.
I'm afraid you are not going to be able to use the 'send as' facility on any member of such a group.
Either move the user to another group or change the e-mail address to suit your needs.
EG:
Lets say you want to 'send as' administrator:-
a) change the administrator's email from {[email protected]}to {[email protected]} and disable automatic recipient policy updates for the user.
b) Create a distribution group for {[email protected]}and set administrator as a member so they receive messages as they would have before.
c) set the send as permissions on the distribution group {[email protected]}to allow users to send as, including the administrator user.
This is technically a workaround, not a solution.
by: ExchisaPosted on 2010-06-21 at 08:07:03ID: 33037008
Dear All .
I still stuck to have this feature working perfectly .
Now I don't want to use this feature to enable users to send as by each other , i only want the users on any given group to send by the name of this group , i did not configure any thing in the ADUC snap in , i only configure this feature from the EMC .
i recieve this error from outlook 2010 :
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.
I surprised that this feature are working sometimes and sometimes not (this is the truth).
does this feature need a CAL like archiving ??
Wait a reply  
by: totallytontoPosted on 2010-06-21 at 08:39:56ID: 33037354
No you do not need a CAL for this.
Is the mailbox that you are sending as still a member of a protected group in AD?
If yes, send as permissions will be reset at random intervals and cannot be changed as long as the user is a member of the protected group.
by: ExchisaPosted on 2010-06-22 at 01:43:00ID: 33043673
totallytonto:
No It's NOT .
Thanks
by: ExchisaPosted on 2010-07-25 at 15:37:57ID: 33285888
totallytonto : I leave configure this from the EMC , instead , i use the ACL for that group in AD , in order to enable SEND AS , just tick the send as permission  

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