If you have checked all of the above and Outlook is disconnected still from your on-premise Microsoft Exchange server, you may indeed have a problem with your server certificate. How To Further Troubleshoot When Outlook Is Disconnected you have internet access on the affected computer, your network DNS settings are correct and you can successfully ping your Exchange server). I’m assuming here that, other than the MS Outlook connection issues with your local Microsoft Exchange server, there are no connectivity problems (i.e. If you have ruled out that “work offline” is not the reason that Outlook is not connecting to your Exchange server, then we can start to look further and see what else needs to be done to restore connectivity.
