Outlook/O365 "sent on behalf" behaviour

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loungebob

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Outlook version
Outlook 2019 64-bit
Email Account
Office 365 Exchange
Coming back to the woman who knows it all. Trying to figure this out through google gives me headaches although I think I know the answer from an EDU post but let's confirm it.

Sending emails from Outlook through an Exchange Server (in this case Outlook 2019 using O365 Exchange) with properly configured rights and delegates and all using the "Sent on Behalf" function only works within the same exchange domain (so basically internally) or when sent from an Exchange Server to a recipient using an Exchange Server as well....not sure which of the two it is BUT it does NOT work properly when sent outside Exchange, right?

I can see the "Sent on Behalf" when sending inside the same domain where all are connected to the Exchange Server but once I send it to G Suite managed accounts or some other environment all mails are shown as being sent from and as the originating email address, the "Sent on Behalf" is totally ignored and not displayed anymore.

I cannot test what happens outside the same domain but still using Exchange Servers on both sides, I don't have access to another domains Exchange account.

On top of it all, it also seems to be an Email Client issue. My iPhone mail app ignores the "Sent of Behalf" even for the same domain connected to an Exchange Server, whereas the same email displayed in Outlook shows the "Sent on Behalf" in the Email address line.

Is it just me or is this (Exchange) feature useless if it only works in such a restricted way?
 
Flattery will get you everywhere. :)

I can see the "Sent on Behalf" when sending inside the same domain where all are connected to the Exchange Server but once I send it to G Suite managed accounts or some other environment all mails are shown as being sent from and as the originating email address, the "Sent on Behalf" is totally ignored and not displayed anymore.
This really depends on the recipients mail client. The information is still in the header (or was, the last time I checked) but is only displayed if the mail client supports it.

I don't think its useless. It is definitely handled best in Outlook and Exchange, but the address is exposed in the header.

Outlook shows me the sender.

2786


Gmail shows it was from Lois Lane. But the header has the sender:
From: Lois Lane <loislane@officepreview.com>
Subject: Testing lois
Thread-Topic: Testing lois
Thread-Index: AdVI4p5LiVoTexuTRPeh7GVimAwP0Q==
Sender: Jenny Wren <jenny@officepreview.com>
 
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