Issue in Outlook 2013 - cannot reschedule single task

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Outlook version
Outlook 2013 64 bit
Email Account
Hey there,

I have a strange issue with Outlook 2013 (Office 365). I have manually entered several tasks in the small task overview bar in the email tab. Now, if I am not mistaken, I should be able to reschedule tasks by right-click -> "Follow Up" -> "Tomorrow/next week/etc."

However, this only works when I select multiple tasks via Ctrl-click. When I select a single task, my only options under "Follow up" are Flag Massage, Mark complete and delete task.

When I go to my tasks tab, the same problem manifests in a different manner: The "Follow Up-flags" appear between "Manage task" and "Current view" - but ONLY when I select multiple tasks at once. They immediately vanish upon selecting a single task.

Any help would be appreciated. :)
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