SendSafely Buttons are disabled / greyed-out

The grayed out buttons typically occur when Outlook is launched by another program in a limited execution mode. The most common example of this is when another program opens Outlook using a "Send Email" button. Clicking a link to create a new email from a webpage (using mailto:) also results in this behavior. 

To avoid this scenario, you should always launch Outlook directly from the Windows Start Menu or a Desktop Shortcut.