If you're going on vacation or will be away for a while, it's common to set up an away message to remind people that you won't be around to respond.
However, if you need to send away messages to people outside of your company, the built-in "Automatic Replies" feature in Exchange will not work.
About Automatic Replies
The Automatic Replies feature does have an option to reply to messages received from both inside and outside your organization, but due to the way Microsoft developed the feature, it no longer works with external Gmail users (and likely won't work for other providers like Yahoo, Outlook.com, and Apple iCloud).
This excerpt from the How Do I Set Up Out Of Office Assistant knowledge base article explains the problem:
It is a known issue that Out Of Office messages, along with other autoreplies, fail the DMARC check, particularly with Gmail accounts, which require DMARC compliance.
This occurs because these messages are sent with a null value in the envelope From address, a design choice intended to prevent potential autoreply loops.
As a workaround, configure Out Of Office reply as a server-side rule.
Create Server-Side Rules In Outlook
As an alternative to using the Out of Office assistant, you can create a server-side rule to set up an auto-reply.
Note: using server-side rules allows you to get around the one reply to one sender limitation. You do not need to have Outlook or OWA open for the rule to work. It also allows you to get around the DMARC failure issue.
1. Navigate to the Rules Wizard in Outlook
Click Home > Rules > Manage Rules & Alerts.
2. Create a New Rule
Under E-mail Rules select New Rule to create a server-side rule. A Rules Wizard window will pop-up.
3. Create a Blank Rule
Select Start from a blank rule > Apply rule on the messages I receive. Click Next.
4. Select the Rule Condition
If you want to send automatic replies to all messages, click the where my name is in the To or CC box checkbox. Click Next.
5. Create Your Away Message
Check the have server reply using a specific message box and click on the words a specific message under the Step 2 area.
Enter the text and the subject of your auto-reply message. We recommend using the "Automatic Reply" for the subject.
Do not use personal phone numbers or email addresses in the message body. This message will be sent to everyone that emails you, including spammers/scammers.
Click Save & Close and then click Next.
6. Autoreply Exceptions
Add exceptions to the rules if necessary. Click Next.
7. Use "Autoreply" for the Rule Name
Enter the rule name, make sure the Turn on this rule box is checked and click Finish.
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