Outlook 2010 and newer have a "Tasks" Jump list, allowing you to quickly create new items by right-clicking the Outlook icon in the taskbar.
Sometimes, the jump list doesn't work properly or disappears altogether, usually after updates or a re-install of Office/Outlook. There are two workarounds to resolve this, both through the registry:
Replace the number in blue with the numeric version of your Office version:
If the first method does not work, try the following: