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Please help me understand this strange (to me) behavior

Goal

Allow delegated users to send-on-behalf-of other mailbox using OWA and iOS/Android apps.

Sent items should appear only once in the delegated mailbox (no sent item should be duplicated anywhere).

Configuration

Delegate has Full Access + Send On Behalf Of permissions to delegated mailbox


OWA Scenario 1

Messages sent on behalf of this mailbox will appear in the Sent Items folder of the: Sender mailbox

Delegates can send email from delegated mailbox - sent items appear only once in the delegated mailbox.

This is great from a desired behavior standpoint, but the Sender mailbox setting should cause the sent item to appear in the delegate's mailbox right?


OWA scenario 2,3

Messages sent on behalf of this mailbox will appear in the Sent Items folder of the: From mailbox

or

Messages sent on behalf of this mailbox will appear in the Sent Items folder of the: Sender and From mailbox

Delegates can send email from delegated mailbox - sent items appear twice in the delegated mailbox and not at all in the delegate's mailbox. Why??

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Try to run the following commands to see if the Send On Behalf Of permission was granted to the delegates successfully, and to trace the sent items which were sent from delegates:

Send On Behalf To:

Get-Mailbox -Identity "<Mailbox Name>" | fl GrantSendOnBehalfTo

Get-MailboxSentItemsConfiguration -Identity "<Mailbox Name>" | fl SendOnBehalfOfItemsCopiedTo

Message Tracking Log:

Get-MessageTrackingLog -Sender <Delegate Email Address> -Recipients <Recipient Email Address> -MessageSubject <Subject> -Start <Start Date and Time> -End <End Date and Time> | ft TimeStamp, EventId, Source, Sender, Recipients, MessageSubject -AutoSize

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