Dear Ian Martin
Thank you for posting in Microsoft Q&A Forum.
From your description, I can understand that in your Classic Outlook, when you manually type a Zoho alias into the "From" field - Outlook shows the message as send "on behalf of" your primary address, and the alias does not appear in the from drop-down list.
Let me break it down for you:
In Outlook, an address can send without "on behalf of" only when it's recognized as a mailbox identity that exists in the Outlook profile. And when an address is not a mailbox identity and instead typed manually into the From field, it's treated as an external sender and formats the message as "on behalf of".
I'd recommend checking on the Zoho side, you should ensure the address is added as Mailbox aliases - not an external "Send email as" address, to avoid "on behalf of", you must either:
- Send from Zoho's web/mobile clients
- Create the address as a real mailbox and add it to Outlook
Thank you for understanding.