If Outlook is always starting offline, make sure you have an active internet connection. Fixes to Outlook Keeps Reverting to Offline Mode 1Check Your Internet Connection Below are some effective methods to fix this problem. There are several reasons why Outlook may start offline as we mentioned above, it may be due to a bad internet connection, or other purposes. My Outlook Is Offline, How Can I Set It to Start Online Part 2: How to Fix Outlook Data Loss Issue.Part 1: My Outlook Is Offline, How Can I Set It to Start Online.