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Send automatic out of office replies from Outlook - Types of OOF rules
You should be able to determine whether the OOF reply has been triggered and sent to an external or internal recipient. The message trace will clearly indicate whether a transport rule is blocking the OOF response. There's one scenario that's worth highlighting when it comes to transport rules blocking OOF replies. Let's assume that you moved the MX record to a third-party anti-spam program.
You have created a transport rule to reject any email message that's sent from any IP address other than the third-party anti-spam program. Description: If the message: Is received from 'Outside the organization' Take the following actions: reject the message and include the explanation 'You are not permitted to bypass the MX record! To fix this issue, change the "Match sender address in message" transport rule property to "Header or envelope", so that the checks will also be done against the From also known as "Header From" , Sender , or Reply-To fields.
For more information about mail flow rule conditions, see the "Senders" section of this article. Additionally, journaling email messages may also be affected. A recommended practice is to create a dedicated mailbox for the JournalingReportNdrTo setting.
Alternatively, you can set the dedicated mailbox to an external address. For more information about how to resolve this issue, see Transport and mailbox rules in Exchange Online or in on-premises Exchange Server don't work as expected.
It can be checked in any of the following locations:. For information about how to resolve this issue, see this article. As an example, assume that you have a hybrid organization that includes mailboxes that are hosted both in Exchange on-premises and Exchange Online.
You also have the option at the mailbox configuration level ExternalAudience: Known to send external OOF replies only to people who are listed as your Contacts. Run the following command to check the configuration:. Another setting on remote domains is one that you use to allow or prevent messages that are automatic replies from client email programs in your organization.
If the value of the setting is false , no automatic replies will be sent to users in that domain. This setting takes precedence over the automatic replies that are set up at the mailbox level or over the OOF type as discussed earlier. Keep in mind that true is the default value for new remote domains that you create and the built-in remote domain named Default in Exchange Online. And false is the default value for the built-in remote domain named Default in on-premises Exchange.
When you investigate an OOF reply issue, you might find the following error entry in the message trace:. Client blocked from sending from unregistered domains. If you find this entry, contact Microsoft Support to learn why the unregistered domain block was enforced. In the message trace, you may see a Drop event with a description that resembles the following example:. When Exchange Online generates OOF replies, it generates and sends both internal and external replies.
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