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Office 365 (Outlook 2016) - Outlook Troubleshooting and Profile Rebuilding
A comprehensive troubleshooting guide with resolution steps for Outlook issues
Common Outlook Errors
Network Connectivity Error

Outlook will present the user with this error message when it cannot connect to the Internet.
Resolution
To resolve the issue, please troubleshoot Internet connectivity issues before proceeding with additional Outlook troubleshooting. To troubleshoot Internet connectivity, we recommend opening a public web page in your browser to confirm your computer can connect to the Internet and contact a non-campus server. Opening a website such as Google or Microsoft. If the workstation is connected to the Internet and the error persists, additional troubleshooting will be necessary.
This issue can also be caused by improper/invalid credentials. In such case, rebuilding your Outlook profile should resolve the issue.
Outlook Disconnected / Cannot Connect to Server
Outlook can report failure to connect to the server for various reasons. Sometimes this network error occurs when your workstation's Internet is working properly and the above troubleshooting does not resolve the issue. This means that the connectivity issue is likely isolated to Outlook.


Resolution
After eliminating the possibility of an Internet connectivity issue (above), make sure that Outlook has not been inadvertently set to "Work Offline" mode. To confirm that this setting is not enabled, navigate to the "Send/Receive" tab in the ribbon. Then confirm that "Work Offline" is not enabled.
Outlook usually displays when it is set to "Work Offline" mode in the status bar, but sometimes shows a "Disconnected" status instead.
Outlook Does Not Sync Changes Back to Server
Staff sometimes report that messages that they either move to other mailboxes or delete from the inbox does not sync back to the server.
Resolution
This can be a sign that Outlook needs to be configured in Non-cached Exchange Mode. Instructions for disabling Cached Exchange Mode can be found here: Office 365 (Outlook 2016) - Cached Exchange Mode