PROBLEM
When selecting multiple objects in outliner using shift key, only the first selected object is active, while subsequent selection do not change what the active object is. This goes against Blender’s viewport selection where the active objects is always the most recently selected ones. This causes destructive issues when for example attempting to join multiple object selected in outliner.
SOLUTION
Obviously, outliner selection should always make the most recently selected object active, to be consistent with viewport selection.