SCENARIO:
It has occurred that when emails on Azure that need to be forwarded externally to a public email can come with issues such as Azure routing to ProofPoint Essentials failed due to relay error or perhaps to security policy on Azure. How to overcome this obstacle.
SOLUTION:
What needs to be one on Azure is enable forwarding for a particular mailbox and create a spam policy to allow external forwarding. It will also provide the outbound logs in ProofPoint Essentials the delivered external email.
1- Sign-In to the Office 365 Admin portal.
2- Click on Admin menu this will launch Admin Center
3- In the Admin Center click on Show All.
4- On the left hand panel select Users - Active Users and then select the account you would like to have forwarding setup for.
5- In the User account Properties page select MAIL and then select Manage email forwarding.
6- On the Manage email forwarding page, enable the option Forwarding all emails sent to this mailbox and enter the external email address in which to forward the email too. Then select the option Keep a copy of forwarded email in this mailbox then click the Save changes button.
7- Close the Manage email forwarding page which will return you to Microsoft 365 Admin Center.
8- On the left panel under Admin centers, select Security this will take you to Microsoft 365 Defender.
9- On the left panel under Email & collaboration select Policies & rules then click the link Threat Policies.
10- In the Threat policies page under Policies select Anti-spam.
11- In the Anti-spam policies page, you will need to create a new new outbound policy by clicking Create policy then select Outbound.
12- Provide the policy with a name and click Next.
13- Next in the Users field type in the Azure account that will be doing the forwarding and click Next.
14- On the next screen under Automatic forwarding rules select On - Forwarding is enabled and click Next.
15- The next screen is simply a review of the policy and click Create button then Done button.
16- Your new policy is now created and forwarding emails to external email accounts is now activated for a particular mailbox. What is a plus is that when emails are sent to that external email account it will us the send connector from O365 to ProofPoint Essentials. This means that outbound email will show up in ProofPoint Essentials outbound logs.