I have an Executive Assistant (Sally) who is basically a super-duper-delegate.   Her account has Delegate access, Send on Behalf and Full Mailbox access to 10 Executives in the company.  (executives also have other assistants that are setup as delegates, which has it's own host of issues that are well documented on Microsoft...)

There are 2 issues today to address that I have not found answers to:

Background:  Server = Exchange 2010, SP3, RU 10.   Client = Outlook 2013 SP1

1.- Sally sends an email to people using send on behalf of Executive "Bob".   The email goes out, no problem.    Sally then needs to send an email out on behalf of Executive "Tom", she swears and double checks to make sure "Tom" is in the "From" field and hits send.   Recipients get the message and it says it came from "Bob" not "Tom".   Does having full access, delegate, send as to multiple accounts cause Outlook 2013 to wig out and send as the wrong account?

2.  Sally has the ability to send on behalf of about 10 people,  But the Autocomplete Cache only shows the last 2 or 3 people she has sent as in her selection "From" field.   That list changes with each new message sent as different person.  Does Outlook 2013 have a limit to the number of remembered/cached names in the autocomplete list for the "From" field?

Finally - are there other known issues with either having "Full access" to 10+ multiple accounts (using automapping to have Outlook attach to all the mailboxes)?   And, are there known issues with having Full Access plus Send on behalf plus Delegate access to all those mailboxes?  (this may be more of an Exchange question than an Outlook question)

Hi,

Generally, it is not recommended to open too many shared mailboxes (full access permission) in the same profile (Exchange AutoMapped or Add additional mailbox in Advanced tab of account settings) at once.

In your scenario, there are 10 accounts opened in Sallys Outlook profile. And multiple permissions are added for this super-duper-delegate. Personal suggestion, we can setup multiple profiles for these shared mailbox for better Outlook performance.

Please disable the AutoMapping for these mailbox in Exchange server and follow the articles below to add shared mailbox as an additional Exchange account:

http://www.msoutlook.info/question/841

Additionally, please also read the following KB:

https://support.microsoft.com/en-us/kb/2297543

Regards,

From what I'm finding - if you use Full Access/Automapping or if you go into the users's outlook profile and add additional full access accounts (not automapped) but thru the profile, (account Settings, More settings, Advanced) - in both cases all the accounts are combined into the single OST for that profile.   The only way to separate them is to set up multiple profiles in Outlook, as you suggested.   But, According to this article:    https://support.microsoft.com/en-us/kb/981245 that method is not supported by Microsoft and can cause issues.

In this particular case, the Exec Assistant has full access w/ automapping, plus Delegate and Send on Behalf permissions all set at the Exchange server level.  On Outlook there are no additional settings.  She open outlook and all mailboxes open in the Nav pane, but they are not configured thru the local profile.  They are taking advantage of automapping.  

The OST is currently over 16GB with the combined mailboxes.   Cached mode is on, but being 2013, it is set to default of storing 12 months local.

So, my options are,

1.  Use Full Access/Automapping = large OST = quirky issues and problems

2.  Use Full Access/ no automapping and add the additional mailboxes in the EA's profile = Large OST = quirky issues and problems.

3.  Use Full access/no automapping and set up multi-ex profiles in outlook = several smaller OST files, but still reported quirky problems with Outlook.

What is the lessor evil here?