Outlook 2010 with multiple exchange accounts with delegates

A client wants to have the Delegated Access functionality for his administrative assistant and also wants to be able to manage his two Exchange Accounts from his single profile in Outlook 2010.  I realize this is not a supported configuration.  Microsoft says on this technet page, http://technet.microsoft.com/en-us/library/ee815819.aspx, "Delegate accounts are not supported in profiles that have multiple Exchange accounts. Users who have delegate access to a mailbox must keep that account in a separate profile from any other Exchange account.".    I have also looked at this Microsoft support page which gives a workaround, http://support.microsoft.com/kb/981245.  Has anyone tried this?  And if so, what are the downsides in functionality?  He wants to be able to manage all aspects of Outlook for his multiple Exchange accounts, ie, meeting requests, Contacts, calendars, and emails both sending and receiving from his one profile.  And is also demanding his administrative assistant be able to manage all the same things from an "On behalf of" delegated perspective.  The client is in the financial services industry and the compliance and regulatory requirements demand that all communications are journaled and require distinct delineations about email origination whether from the actual sender or from the administrative assistant.  The client DOES NOT want to work out of multiple Outlook profiles (thinks it's too cumbersome), DOES NOT want to have a separate VM running real-time with a different instance of Outlook with a different profile for the second Exchange account, (thinks it's too cumbersome), DOES NOT want to use OWA (too cumbersome), has two Exchange accounts and is demanding the delegated access functionality for his administrative assistant.  

His configuration requirements are even more challenging for his administrative assistant.  Not only does he want her to manage her two Exchange accounts from her single profile but he wants her to be able to manage his two Exchange accounts as well as a third Exchange account for another partner as a delegate?

Any input about this workaround and/or alternative suggestions would be greatly appreciated.  I'm really stuck between a rock and a hard place.  He's asking us to give him something that Microsoft says will not work but he still wants what he wants?
jdancelSr Network and Systems AdministratorAsked:
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unless i completely misunderstood the question:
open his other accounts as additional mailboxes in his outlook , so he has all mailboxes under one profile?
then add the "from" field to his outlook and make sure he has the send-as right in exchange
and the same for the assistant?
jdancelSr Network and Systems AdministratorAuthor Commented:

Thanks for such a quick response.

As mentioned in my post, this sounds like the workaround in http://support.microsoft.com/kb/981245.  Is there any loss in functionality using this workaround or any issues I should be aware of when deploying this?  

When giving the Send-as right for the second exchange account, will emails be sent "On Behalf of"?  In other words, will it say "On behalf of John Doe from John Doe?"  Both of his email accounts have the same name but different email domains.  For example, JohnDoe@abc.com and JohnDoe@xyz.com, but the actual name on both accounts is John Doe.  We had to do this because the emails for each email domain MUST remain separate.  If the emails would be labeled "On behalf of John Doe from John Does", the client would not want this.

As far as the assistant's delegated access, do I need to provide Full Permissions as well as Send As Permissions on the Exchange Server for all 3 Exchange Accounts so she can see the Calendars, Contacts, etc.?
no problem.

It will not reduce functionality, other then the hassle of the user having to monitor several Mboxes in the left pane in outlook, but this is acceptable.

the send as is not the same as on behalf.
When a user has send as rights, he can add the "from" field in outlook and enter the desired from address. the mail will seem to come from that user. The user should just type out the mail he wishes to send from , or select the correct one from the GAL

for the assistant:
if he doesn't need to send as, then you do not need to give that permission.
For the calendar and mailbox viewing it's enough to give full access to the box.

Hope it helps

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jdancelSr Network and Systems AdministratorAuthor Commented:

I tried to deploy this workaround early this morning while the client was out of his office.  When sending the emails, the sent email from the "Additional Mailbox" went into the sent items for the Primary Account?  This cannot happen for compliance reasons.  As I had indicated, this implementation is for the highly-regulated financial services industry.  The primary account is journaled and sent to a compliance department.  Emails mixing between the two accounts is a definite no-go.  Any other suggestions?
I must check this out. I'll get back to you

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jdancelSr Network and Systems AdministratorAuthor Commented:
Client doesn't want to change his work processes and we have to regularly recreate his profile when it gets corrupted.  Thanks for your help anyway.  The correct answer would have been not to deploy this configuration when MS recommends against it.
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