Can't send from another email address when in Cache mode Exchange 2010/ Outlook 2010

Hi Experts,

I'm trying to track down an issue I have with sending emails from other email adddresss on the same AD/Email account.  I.e. I have users with multiple email addresses, but when they try using the FROM field to change from the default email address it wont work.

This has nothing to do with users trying to send via another mailbox and I do appreciate that to the recipient it will only ever look like hes getting it from the default reply email domain.

The problem only occurs when Outlook is in Cached mode.

I think it's something to do with the Offline Address Book, but I need expert advice to help track down this issue.

Thanks.
jmsjmsAsked:
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Jamie McKillopConnect With a Mentor IT ManagerCommented:
My guess would be that whatever the user is doing, when in non-cached mode the address is resolving immediately to the address book but it is not resolving when in cached mode. If the user types the address and does an Alt+K, it would resolve to the address book and send.

-JJ
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Jamie McKillopIT ManagerCommented:
Hello,

You can't send from a secondary SMTP address, whether you are in cached mode or not. Exchange will always send as the primary SMTP address on the mailbox. If you want to be able to send as one of the secondary addresses, you would need to move that address to another object, such as a distribution group, as the primary address on that object. You would then give the user send as rights to that object.

-JJ
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jmsjmsAuthor Commented:
Thanks for the confirmation.

Outlooks behaviour is a little misleading.

When not in cache mode, it will allow a user to select another email address from the list of email addresses the user has been assigned via the Global Address Policy in FROM box.  It will then send the email but it will appear to the recipient that it's come from the default reply email address (set in exchange).

However, in cache mode it wont do anything but the default email address.

Whislt I now know changing the email address is pointless as the reciepient always sees the email as cominig from the default reply address, it's a bit weird that it has an error in cache mode and not in non-cache mode?

Is this expected behaviour with cached/non-cached modes or is there something wrong?
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jmsjmsAuthor Commented:
Yep, this seems to work, but whys it not resolving in cached mode? Or is this expected?
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Jamie McKillopIT ManagerCommented:
I would have to know the exact steps your users are taking to comment on that.

-JJ
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jmsjmsAuthor Commented:
Well I'm testing using my own account, my steps are in 39881991

Is there something in particular to look for?
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Jamie McKillopIT ManagerCommented:
When in online mode it is resolving right away, When it cached mode, it isn't resolving before it hits the server. This is normal.

-JJ
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jmsjmsAuthor Commented:
So it's normal for the error to occur in Cached mode and not in non-cached mode?

I thought the OAB was supposed to resolve things in cached mode?

(THanks for the help BTW, it's helping me understand a bit more!)
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Jamie McKillopConnect With a Mentor IT ManagerCommented:
You need to hit alt-K to resolve an SMTP address you type to the address book. SMTP address will not automatically resolve. So, yes, it is normal.

-JJ
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jmsjmsAuthor Commented:
OK.  Many thanks.

Final query.  Whats the point of the OAB then?  Is that only for recipient details?
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Jamie McKillopIT ManagerCommented:
The OAB is an offline copy of the address book. The issue is that Outlook behaves slightly differently when in cached mode version online mode and you have discovered one of the differences.

-JJ
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jmsjmsAuthor Commented:
OK Thanks
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