OUTLOOK FORWARDING NOT WORKING

A likely reason is that automatic forwarding is being blocked for the destination or by account policy, while the legacy client is using a different forwarding method.

Supported differences from the documented behavior:

• New Outlook / Outlook on the web uses Settings > Mail > Forwarding to enable mailbox-level forwarding.
• Classic Outlook can forward mail by creating an Inbox rule.

If forwarding works in legacy Outlook but not in new Outlook, check these conditions:

1. In new Outlook, go to Settings > Mail > Forwarding and confirm Enable forwarding is turned on, the destination address is correct, and Save was selected.
2. If prompted on the Forwarding and IMAP page, complete Sign in authentication first. Otherwise, forwarding settings may not become available.
3. If the destination is an external recipient, automatic forwarding can be blocked by outbound spam filtering. When that happens, rules that forward to external recipients do not work by design and can generate nondelivery reports.
4. If forwarding is configured through an Inbox rule, forwarding can also fail by design when:
   • the message was already forwarded once,
   • the rule tries to send back to the original sender,
   • the mailbox domain matches a listed domain where redirect rules do not work.
5. For Outlook.com rules, forwarded or redirected copies remain in the mailbox. If the mailbox exceeds its limit, sending/receiving can be blocked and forwarding rules may stop working until enough mail is deleted.

Since the source is an Outlook.com personal account and the target is a business domain, the most relevant documented cause is external automatic forwarding being disabled for the external recipient.

• Turn automatic forwarding on or off in Outlook | Microsoft Support
• Diagnose Outlook Inbox rules that aren't working
• [Outlook.com](https://support.microsoft.com/outlook/mail/use-rules-to-automatically-forward-messages#what-else-do-i-need-to-know)