In Outlook, how can you ensure that a specific individual always receives a notification when you are out of the office, regardless of their location or email domain?

To ensure a specific individual always receives an out-of-office (automatic reply) notification in Outlook, regardless of their location or email domain, you should add their email address to both the 'Inside My Organization' and 'Outside My Organization' sections of your Automatic Replies settings. Outlook's Automatic Replies feature typically offers separate settings for internal and external senders. The 'Inside My Organization' tab allows you to configure a message for colleagues within your company. The 'Outside My Organization' tab allows you to configure a message for senders outside your company, which can be further segmented into replies for 'My contacts only' or 'Anyone outside my organization'. By adding the specific individual to your Outlook contacts and configuring the 'Outside My Organization' reply to include 'My contacts only' and adding that user to the contacts ensures they get an external automatic reply. However, the most reliable method is to explicitly add that individual to both the 'Inside My Organization' (even if they are external) and 'Outside My Organization' sections with the same message. This ensures that regardless of how Outlook identifies the sender (internal or external), they will always receive the automatic reply. This approach addresses potential issues caused by domain configurations or changes in email routing that might affect how Outlook classifies senders. It is important to save these settings for them to take effect.