As of June 2022 Microsoft made a configuration change that will only send 1 automatic reply to an email address. You can turn automatic replies off / on to reset the "History" associated with an auto reply. This will allow users to receive updated information but they will only receive one automatic reply. Outlook Mac With Outlook for Mac open, click on Tools, then click on Automatic Replies.... Click on Send automatic replies for account j123h456@home.ku.edu. Type your automatic reply message to KU users in the box under Reply once to senders within my organization. If you select Send replies only during this time period, you can choose the dates and times that your automatic reply will be active. Click on Send replies outside my organization to send automatic replies to non-KU users. Type your automatic reply message to non-KU users in the box under Reply once to senders outside my organization. Click OK Windows Click File in the top left of your screen. Click Automatic Replies (Out of Office). Click Send automatic replies. If you select Only send during this time range, you can choose the dates that your automatic reply will be active. On the Inside my Organization tab, type the response that you want to send to KU users while you are out of the office. On the Outside my Organization tab, type the response that you want to send to non-KU users while you are out of the office, -OR- turn this feature off by unchecking Auto-reply to people outside my organization. Outlook Web App (OWA) Login to your KU email account at https://outlook.office.com. Click on Settings (gear icon) in the upper right of your screen. Click Mail in the far left menu, then click Automatic Replies in the menu to the right. Click Turn on Automatic Replies. If you select Send replies only during this time period, you can choose the dates that your automatic reply will be active and configure calendar settings for the time period. Type your automatic reply to KU users under the box Send automatic replies inside your organization. Click on Send replies outside your organization to send automatic replies to non-KU users, and type your message in the box underneath that selection. Click Save at the bottom of the Settings window to complete the setup.