An electronic mail (email) system generates an email user interface display, that allows the user to enter message content. A context-sensitive calendar preview can be triggered and displayed on the email user interface display. The email system detects a user drag and drop input dragging at least a portion of the message content onto the calendar preview, and automatically generates a calendar event based upon the detected drag and drop input, and the particular portion of the message content dragged onto the context-sensitive calendar preview.