That’s because you are displaying the first task in your user’s task list, as per your drag/drop group data source.
You do need a repeating group to display a list of items and not just the first item. Searching for a list of tasks or a list of users:each item tasks will result in the same layout, tasks/user’s list of tasks will be displayed on separate rows/columns.
So, use either of the 2 RG searches and if you really want to display the tasks as list, apply the below condition to you Text Current column’s Task.