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Note

Email Aliases in Microsoft 365 take 24 hours to become valid, prior to this they will be rejected (shown below).

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O365 Doesn't always retain the inbound Alias address

(warning) O365 doesn't yet support this, the feature is there in JEMHC, described here:the ‘Delivered-To’ header for Alias addresses (even when the mail is routed correctly, JEMHC has no way to determine what that Alias is, reliably).

Anecdotal comments from a customer using o365:

… Exchange Online is writing the To: header differently based on if the message is sent internally or externally. Messages sent from inside our Exchange organization always get the primary SMTP address, while messages sent from external senders write the actual address.

Retaining in the incoming address in outbound mail

You may also want to retain the incoming ‘alias’ address for use in all outbound notifications. The support for Aliases, as covered in the prior section is not not guaranteed, in such cases, all you get is the common primary mailbox address. JEMHC does this through Custom Field defaults:We encourage o365 customers to engage with MS support on this topic.

JEMHC can store inbound address in a Custom Field default

  1. Storing the$catchemail (see end of : Setting a custom field value )

  2. Using the custom field during sending

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  1. :Changing the from: address used (statically or from a Custom Field)

We found the following on the web (cannot really dig more into o365 mail configuration):

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