SYMPTOM:
When a check box selector's All option is initially checked, all elements are checked as well in Strategy Web 9.x and 10.x. When an element is unchecked, the 'All' option is unchecked as expected. However, when the element is rechecked, the 'All' option is not rechecked again.
STEPS TO REPRODUCE:

CAUSE:
This is working by design. When all the elements are selected, whether or not the 'All' option is checked, the data on the grid stays the same. Both states are correct. In order for the 'All' option to be checked every time the selections change, it must check whether or not all the elements are selected. This will cost some resources and may affect performance. For that reason, it was not implemented.
ACTION:
Check the 'All' option manually or leave as is.