Microsoft Outlook doesn't connect or isn't sending and receiving Symptom: You have an active internet connection (test by opening a webpage) and Outlook is fully functional, except it does not seem to download new mail, and outgoing mail is not sent. Cause: Outlook may be on “Working Offline” mode. This mode assumes you are not connected to the internet, so it does not attempt to send or receive mail. Solution: Open Outlook Check the lower-right corner of the window for an icon with a small red circle with an “X” and the word “Offline”. Click the icon. A submenu will appear. Click “Work Offline” to uncheck the option It may take several seconds for the application to reconnect and transfer mail.