Items sent as appearing in sent items as sent on behalf of

Question

Items sent as appearing in sent items as sent on behalf of

Lilly Hill 20

Hi all,

I have a user who has Send as and does not have Send on behalf of permissions to several shared mailboxes.

They are logged into a primary account and another mailbox as their secondary. All permissions to the shared mailboxes are granted via their primary account.

When they send emails out from the address of one of the shared mailboxes the emails arrive looking like they were sent from that shared mailbox - which is what we want.

The sent items go into the sent items folder of the primary mailbox - which is what we want.

However, the sent items appear in the sent items folder showing sent on behalf of the shared mailbox, rather than just showing from.

Untitled

It needs to show from the shared mailbox. It used to show from the shared mailbox. Unfortunately the user cannot pinpoint exactly when it changed so it is hard to say what was changed at the time.

Can anyone point me to a solution?

The setup is hosted exchange 2016.

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Answer 1

Kael Yao 37,746 Moderator

Hi @Lilly Hill

Resolution:

If the shared mailbox is manually added to the From field in Outlook, delete this auto-complete entry from the drop-down list and re-add it from the address book.

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Lilly Hill 20 Reputation points

2023-10-25T08:03:47.5466667+00:00

It doesn't sound like expected behaviour as it was not happening 3 months ago and it isn't happening for anyone else in the business.
Kael Yao 37,746 Reputation points Moderator

2023-10-25T08:07:07.1933333+00:00

What is the Outlook version they (not affected users) are using?
Lilly Hill 20 Reputation points

2023-10-25T08:23:03.46+00:00

All users, affected and not, are on Office 2016.
Kael Yao 37,746 Reputation points Moderator

2023-10-25T08:29:25.25+00:00

Can you share some examples of the affected and not affected users in screenshots?

(Don't forget to hide personal information)
Including:
1.their delegate permission settings in Exchange
2.how are they sending as the shared mailbox

And may I ask what is the main concern in this case?
Lilly Hill 20 Reputation points

2023-10-25T08:36:44.07+00:00

All users are given Send As and Full Access, no users have Send on Behalf of

They are sending as by creating a new email, going to the from drop down, then selecting the correct email address to send from.

The concern is that the sent items are used for strict auditing purposes and need to be accurate.
Kael Yao 37,746 Reputation points Moderator

2023-10-25T08:41:48.9866667+00:00

In EAC there is no send on behalf permissions in delegate settings of shared mailbox.

And if the recipient is seeing the shared mailbox as sender, it indicates the sender is sending as the shared mailbox (not send on behalf).

Can you post screenshots of the symptom of the affected users and other users?
It could help us better understand the situation.

If this is a critical issue, I would suggest configuring the shared mailbox as an additional account (sign-in with the credentials of the primary mailbox) in Outlook or use OWA instead.
While note that it would not keep a copy in the Sent Items of the primary mailbox, only in the shared mailbox.
Lilly Hill 20 Reputation points

2023-10-25T08:46:55.66+00:00
Lilly Hill 20 Reputation points

2023-10-25T08:57:21.6266667+00:00

It seems to have deleted my image showing the send on behalf of option.

Did it come through?

Unfortunately the Audit is run via the main mailbox, hence the use of shared mailboxes. If we wanted the sent items to go into the shared mailbox folders I would have used the relevant reg key change.
Kael Yao 37,746 Reputation points Moderator

2023-10-25T09:10:16.1833333+00:00

It seems the "shared mailbox" is not a real shared mailbox in Exchange.

In normal case a shared mailbox delegation setting page would be like:

Normal user mailbox:
Kael Yao 37,746 Reputation points Moderator

2023-10-25T09:21:54.8066667+00:00

Did the user manually enter the email of the shared mailbox?
Or he selected it from the address book?
Lilly Hill 20 Reputation points

2023-10-25T10:17:36.69+00:00

Manually entered originally, it is now just in the drop down options.
Kael Yao 37,746 Reputation points Moderator

2023-10-26T05:53:31.56+00:00

Thanks for the information!

Please remove this entry from the drop-down list (by clicking X) and select it from the address book to send as this shared mailbox, see if this issue persist.
Lilly Hill 20 Reputation points

2023-10-26T07:56:11.3233333+00:00

Thanks Kael
Kael Yao 37,746 Reputation points Moderator

2023-10-26T07:59:59.29+00:00

Did it help with this issue?
Lilly Hill 20 Reputation points

2023-10-26T08:11:04.75+00:00

Yes, thanks.
Kael Yao 37,746 Reputation points Moderator

2023-10-26T08:17:15.98+00:00

Glad to hear that!

I have updated the solution in the main post. Please feel free to accept it as the answer to help other community members.

Thanks for your understanding.

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Items sent as appearing in sent items as sent on behalf of

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