Status of Button Not Detected

Questions & Suggestions
6

There's your problem. You're testing for a button that doesn't exist.

Try targeting the checkbox with this macro. You can add a condition within the resultant script.

Here's an example using the Preview app:

tell application "System Events"
	tell process "Preview"
		-- Navigate to the checkbox
		set theCheckBox to checkbox "Auto Rotate" of group 1 of group 2 of scroll area 2 of splitter group 1 of sheet 1 of window 1
		
		-- Click the checkbox only if it's checked
		if value of theCheckBox is 1 then
			click theCheckBox
		end if
	end tell
end tell

Obviously you'll need to replace "Auto Rotate" of group 1 of group 2 of scroll area 2 of splitter group 1 of sheet 1 of window 1 with the relevant element reference for your macro.