We can reproduce this on multiple Windows 8.1 machines.
1. Enable Auto-Select and Show Transform Controls
2. Draw 2 or more objects on the Photoshop canvas
3. Select by clicking and dragging down from top-to-bottom around all the objects, but then move the mouse cursor back up so that only 1 is selected.
Note that all objects remain selected.
The issue illustrated in this screen capture. Note that the last item remains selected even though the cursor is now off the region. Last item should be deselected.