How to Create and Out of Office Rule that Applies Every Time

Below are the instructions to create a rule to send an Out of Office reply each time you receive an email.  When you use the standard Out of Office feature, it will only reply to each person one time each time it is enabled.  To send a reply every time, you have to create a Rule instead of using the Out of Office feature. 

1. In Outlook, go into the “Tools” menu and select “Rules and Alerts…”.
2. “New Rule…” button. 
3. Select “Check messages when they arrive” as seen in the screenshot below, then click “Next >”.  
   
4. Select “where my name is in the To or Cc box” and click “Next >”.  
   
5. Check “have server reply using a specific message” as seen in the screenshot below.  Then in the box under “Step 2”, click the link reading “a specific message” (“Out of Office Test”in the screenshot example).  In the email that opens, just enter the desired Subject and Body, then save and close the email.  The Subject you entered should now be displayed as the reply message link in the “Step 2” box.  Now click “Next >”.  
   
6. Optionally setup any exceptions, then click “Next >”. 
7. Give the rule a name like "Out of Office Auto Reply", check “Turn on this rule” (assuming you want to start sending Out of Office replies immediately), then click “Finish”.  
   
8. On the “Rules and Alerts” screen, make sure you click “Apply” and “OK” (and NOT “Cancel, or it will not save the Rule).  You may see a message saying it is updating the Rules on the server. 
9. When you want to enable/disable this Rule, and or change the message, just go to “Rules and Alerts…” from the “Tools” menu, then double click the Rule to go through the options.