What's this icon mean?

So when this icon shows up on an email in a shared mailbox that email when attempting to froward, tries to forward from the senders address.. any idea why this is?

That's the icon to indicate that it is a Draft message.
Also, when you are in a shared mailbox, the From address will default to the address of that mailbox. You need to have Delegate Send on Behalf Of permissions or AD/Exchange level Send As permissions to actually be able to do that.
Robert Sparnaaij
[MVP-Outlook]
Outlook guides and more: HowTo-Outlook.com
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