MessageCopyForSendOnBehalfEnabled is not working as expected

Question

MessageCopyForSendOnBehalfEnabled is not working as expected

Markus Walter 40

Hello everyone,

We are using Exchange on premise 2016 CU22 and Outlook 2016 & 2019.

For a shared mailbox, MessageCopyForSendOnBehalfEnabled & MessageCopyForSentAsEnabled is set to $true.

This mailbox was previously a user mailbox and has been converted to a shared mailbox.

The registry value HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences DelegateSentItemsStyle is set to "1" as mentioned here:

https://learn.microsoft.com/en-us/exchange/troubleshoot/user-and-shared-mailboxes/sent-mail-is-not-saved

Unfortunately, the mail gets stuck in the outbox and is also delivered to the recipient, but is not saved in the Sent Items (neither in the shared mailbox nor in my own). Does anyone have an idea? #

Even if I delete the RegValue it does not work, then the mail can only be found in my Sent Items.

Best regards

Markus

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Answer 1

Anonymous

Hi @SukramRetlaw ,

It is recommended that you use Get-mailbox to confirm that MessageCopyForSendOnBehalfEnabled & MessageCopyForSentAsEnabled is set to $true. Then set the registry value HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences DelegateSentItemsStyle to "1", and use Cached Exchange Mode, restart Outlook, if the problem still exists, you could try to recreate an Outlook profile to see the situation. User's image

Markus Walter 40 Reputation points

2023-12-15T09:19:38.8966667+00:00
Hi @Anonymous

as i stated before MessageCopyForSentAsEnabled was already set to $true as well as MessageCopyForSentAsEnabled

DelegateSentItemsStyle is now present again in HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences and set to "1"

Outlook is in Cached Mode.

Restarted Outlook, now it works. Thanks for that.

But some questions are left:

Is there a way to make this working without having Cached Mode enabled and without the RegKey?

why is this not needed for a new created Shared Mailbox? As i stated in the first post, the Mailbox in question was converted from a user to a shared Mailbox.

Best Regards, Markus
Anonymous

2023-12-18T09:49:29.62+00:00

Hello @Markus，

I'm glad to hear your issue has been resolved. As for your new questions, I will give you a complete answer later.
Anonymous

2023-12-19T08:32:35.3833333+00:00

Hello @Markus，

Regarding the first question, as far as I know, there seems to be no way to make it work without enabling cache mode and without a RegKey at the same time under the premise that setting MessageCopyForSentAsEnabled and MessageCopyForSendOnBehalfEnabled does not work, as you can see in this document Email remains in Outbox if using DelegateSentItemsStyle - Outlook | Microsoft Learn.

As for the second question you mentioned, in theory, there is no difference between user mailbox converted to shared mailbox and ordinary shared mailbox. You only need to make corresponding settings according to the information in the table we mentioned before. If the different phenomena do appear in the usage scenarios, could you please provide relevant screenshots or more detailed information for us to take a look at for the further troubleshooting.
Markus Walter 40 Reputation points

2023-12-20T13:02:39.29+00:00
HI @Anonymous

as you stated it should function as mentioned in the Document(s). As of this i did some more testing with the Mailbox in question. Let me sumarize my findings.

the Mailbox was converted from a user to a shared mailbox (nothing new just to keep in mind)

for the Mailbox a Delivery option is present (Enable Forwarding to another Mailbox)

If i set both Delivery Options (Enable Forwarding AND "Deliver message to both forwarding address and mailbox) Sent Items are saved in the Shared Mailbox and in the Sent Items Folder of the Mailbox to which the forwarding Opiton is set??! Is that crazy or a expected behaviour? This works without RegKey or Cached Mode.

I´ve attached a picture for better understanding.

Best Regards Markus
Anonymous

2023-12-22T06:04:27.9966667+00:00

Hello @Markus，

It is understood that if the "Enable forwarding" and "Delivery mail to forwarding address and mailbox" options are enabled for a shared mailbox, the sent mail will be saved in the shared mailbox and Sent mail folder of the mailbox with the forwarding option set. This is expected behavior.

Regards

Answer 2

Andy David - MVP 157.4K MVP Volunteer Moderator

Hi, have you seen this?

https://learn.microsoft.com/en-us/outlook/troubleshoot/email-management/email-remains-in-the-outbox-when-you-use-the-deleg

Markus Walter 40 Reputation points

2023-12-14T12:09:00.7133333+00:00
Hi Andy,

sure i know those settings. Let me sumarize.

MessageCopyForSendOnBehalfEnabled & MessageCopyForSentAsEnabled is set to $True for the Shared Mailbox

RegKey i tried both without an with

Exchange Cached Mode is off

Best Regards
Markus
Anonymous

2023-12-15T05:33:41.56+00:00

I understand that you have read the documentation provided by Andy, and based on your description, it seems that the cause of the problem is the same as mentioned in the documentation:

Therefore, it is recommended that you follow the method in the documentation to solve.
Markus Walter 40 Reputation points

2023-12-15T06:32:26.2866667+00:00
@Anonymous

thanks for the note, but it does not work at all. Now i´ve the following situation tested:

DelegateSentItemStyle is not present in the registry

Cached Mode is on

Same behaviour, Sent Message are only in my personal Inbox but not in the Shared Sent Items.

Best Regards
Markus

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MessageCopyForSendOnBehalfEnabled is not working as expected

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