Microsoft 365 (Outlook for Windows/MacOS) - Sent or Deleted item is not saved within the sent/deleted items folder of the account actioned from

When you send or delete a message on behalf of another account via Outlook for Windows/MacOS, the message is placed in the "Sent Items/Sent" or "Deleted Items/Trash" folder of your own account and not in the mailbox you are sending/deleting from.

Recommended workaround(s):

 Outlook on the web

  1. Log into Outlook on the web.
  2. Open another mailbox. Open the mailbox which you want to send/delete the mail from.
  3. Send/delete a message as desired.

If you sent a message, it will be saved in the "Sent Items" folder of the account you are in. If you deleted a message, it will be moved to the "Deleted Items" folder of the account you are in.

 Outlook for Windows

Create/Modify Registry object for "Sent Items"

Important: Follow the steps in this section carefully. Serious problems might occur if you modify the registry incorrectly. Before you modify it, back up the registry for restoration in case problems occur and/or contact your IT support staff.

  1. Quit Outlook.
  2. Click Start, click Run, type regedit, and then click OK.
  3. Locate and then click the following registry subkey:
    HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Preferences

    Note:The x.0 placeholder represents your version of Office (16.0 = Office 365 ProPlus, 2019, and 2016, 15.0 = Office 2013).

  4. If DelegateSentItemsStyle entry exists, right-click on it and click Modify. Otherwise, on the Edit menu, point to New, and then click DWORD Value and type DelegateSentItemsStyle, and then press Enter.
  5. Right-click DelegateSentItemsStyle, and then click Modify.
  6. In the Value data box, type 1, Base = Hexadecimal, and then click OK.
  7. Exit Registry Editor.
  8. Restart Outlook.

Now, when you send a message where the "From" address is the account you have permissions to send from, the message will be placed in the "Sent Items" folder of the account you took action from.

Create/Modify Registry object for "Deleted Items"

Important:

  1. Quit Outlook.
  2. Click Start, click Run, type regedit, and then click OK.
  3. Locate and then click the following registry subkey:

    HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Options\General. Important: If the 'General' folder does not exist, you will need to create it.

    Note:The x.0 placeholder represents your version of Office (16.0 = Office 365 ProPlus, 2019, and 2016, 15.0 = Office 2013).

  4. If DelegateWastebasketStyle entry exists, right-click on it and click Modify. Otherwise, on the Edit menu, point to New, and then click DWORD Value, and type DelegateWastebasketStyle , and then press Enter.
  5. Right-click DelegateWastebasketStyle, and then click Modify.
  6. In the Value data box, type 4, Base = Hexadecimal, and then click OK.
  7. Exit Registry Editor.
  8. Restart Outlook.

Now, when you delete a message/calendar event where the from another account, the message/calendar event will be placed in the "Deleted Items" folder of the account you took action from.

 New Outlook for Windows and Outlook for MacOS

Modify account setting for "Sent Items"

Please contact the DoIT Help Desk and provide them with the email address of the account you are interacting with.

Internal Notes

For HD/Support Staff:

Users who are contacting you because they are using Outlook for MacOS, please gather all required handling information, address of netid/service account, and escalate the case to O365/Technical queue. Let the customer know that M365 team will need to modify a setting on the account to enable this feature.


Notes for M365 team

Registry modification: http://support.microsoft.com/kb/2181579

Registry modification: https://docs.microsoft.com/en-us/exchange/troubleshoot/shared-mailboxes/sent-mail-is-not-saved

Sent Items steps: https://blogs.technet.microsoft.com/exchange/2017/03/28/sent-items-behavior-control-comes-to-exchange-online-user-mailboxes/

Other MS resources:

  • https://docs.microsoft.com/en-us/exchange/troubleshoot/administration/email-from-shared-mailbox-not-saved-sent-items
  • https://docs.microsoft.com/en-us/exchange/recipients-in-exchange-online/manage-user-mailboxes/automatically-save-sent-items-in-delegator-s-mailbox

Instructions for support and techteam staff tech team

  • Have tech team run: Set-Mailbox -identity upn_of_account -MessageCopyForSentAsEnabled $true
  • Note: this will place the sent item in both the sender's and sa account's sent folder regardless of the client being used
  • Important: remind customer if users had the registry key modified for this setting (listed above), messages may now get duplicated within sent items folder, you should remember to remove client registry keys if you enable this feature server side.

Deleted Items steps: https://support.microsoft.com/en-us/kb/202517

For Outlook for Mac users, it appears that deleted items already get placed into the service account deleted items folder, so the only PowerShell command that can be run is for the sent messages.

Messages stuck in Outbox but are delivered to recipients

Can't send an email message when Full Access permission is granted to a shared mailbox in Exchange Server



Keywords:
microsoft office365 o365 m365 microsoft 365 send as send on behalf of sent items folder email sent messages deleted items mail calendar event meeting appointment service account netid windows mac os macos outlook 2016 2019 registry proplus events enterprise 
Doc ID:
45343
Owned by:
O365 S. in Microsoft 365
Created:
2014-12-01
Updated:
2025-09-03
Sites:
DoITHelpDesk-external, DoITHelpDesk-internal, Microsoft365-external, Microsoft365-internal