Outlook Is Not Connected
Icon is a red circle with an "x" in it.
While in Outlook view the bottom right corner of window to see if it shows "Connected" or Working Offline.
If the latter, go to the Outlook SEND/RECEIVED tab.
Above the Preferences ribbon, check to see if the "work Offline" option is highlighted. If it is, un-highlight the option by clicking on it.
You can immediately see at the bottom right corner of your Outlook window that the server status has changed from "Working Offline" to "Connected to Microsoft Exchange" or whatever program you are using to send email.