Can Send As a different alias address in OWA, but can't in Outlook using Managed list?

Question

I am trying to send as a secondary smtp/alias, because we have different domains in use.

O365, Hosted.

When i send a mail with OWA the alias works perfectly. When i send from outlook desktop client i can choose my alias and it looks like its working but the sender is than overwritten by the primary smtp.

I tried 3 different outlook client versions but it wont work.

As an example from outlook application

Brad@company.com - default SMTP - sends as expected

brad@company.co.uk - alias address - when sending, delivery address comes through as brad@company.com

Brad@newcompany.com - new alias - when sending, delivery address comes through as brad@company.com

As an example from outlook web / OWA

Brad@company.com - default SMTP - sends as expected

brad@company.co.uk - alias address - sends as expected

Brad@newcompany.com - new alias - sends as expected

Answer 1

Make sure you're typing in the email alias in the From > Other e-mail address box, do not select any stored/autocomplete entry. I'm using an Outlook build that's on the semi-annual channel, and it works fine there.

Another thing to have in mind is that Outlook will resolve the recipient address on the received message against any existing contacts, and doesn't always indicate the alias used. The best way to confirm the address used is to check the From header of the message.

Answer 2

Hi @Brad Wooder ,

Try to clear the autocomplete list: Clear the AutoComplete list Or Start Outlook by using the command: Select Start, and then select Run. Type Outlook.exe /CleanAutoCompleteCache.

Check this link: https://www.howto-outlook.com/faq/aliases.htm and test if it works. (Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)

Answer 3

Hi @Brad Wooder ,

Did you setting on the EXO mail flow settings sending from aliases?

Hope I was Help you

My regards

Paolo