Welcome to UiPath Community !
To know if UiPath is able to “see” the boxes, first use UiPath Explorer:
Then click on indicate element, then indicate the first box.
If no error is returned, screen us the result like this:
Then use again uiexplorer and indicate the second box, and screenshot it for us.
That way we will work together on the creation of your workflow !
For your second query, I am not sure to understand what you are looking for, may you specify ? Do you mean that you want the robot to change the content of a field if there is a specific information ?