Two User mailboxes added in outlook but only one mailbox sent items is showing emails for both

[AmirShahzad]

Hi Team,

I have this problem about two User (not Shared) mailboxes added in one Outlook for windows in windows 10. These mailboxes are Office365 E5 licensed.

When a user sends email from one mailbox @domainA its sent items show the email

When that user sends email from 2nd Mailbox @DomainB added inside the same outlook then this email still shows in the sent items of the first mailbox @DomainA

Is it possible to show email of @domainB in the Sent Items of @DomainB while Sent Items of @DomainA works fine. @domainB sent emails should not show in the Sent Items of @DomainA.

Please help in this regard. will appreciate this.

[#2]

That's not the default behavior, so start by telling us how exactly are the two mailboxes added in Outlook. They should be configured as separate account (via File > Add account) and listed as such accordingly in the File > Account Settings dialog.
Also check whether the "always use the default account when composing new messages" setting is toggled.

[#3]

Hi,
As per your description, I believe that both mailboxes are having full delegation against each other..
Please correct me, if I understood wrongly....

Is it a different Domain or same Domain????
mailbox @domainA
mailbox @domainB

Whenever you sent an email.. Are you choosing the correct mailbox in OUTLOOK before sending emails?

I think you are not choosing the correct mailbox while sending emails that why it is going to MailboxA sent items.

Please ask your Exchange Admin to run the below command, hopefully it will resolve your issues:

set-mailbox -Identity "mailbox@domainB" -MessageCopyForSentAsEnabled $True

https://docs.microsoft.com/en-us/exchange/recipients-in-exchange-online/manage-user-mailboxes/automa...


Thank you,

Regards,
MD

[#4]

@MDadarkar Thank you for your help.

Yes it is two different directories inside Azure AD with E5 License.