Index: wordpress.org/public_html/style/trac/trac-security.js
===================================================================
--- wordpress.org/public_html/style/trac/trac-security.js	(revision 2000)
+++ wordpress.org/public_html/style/trac/trac-security.js	(working copy)
@@ -36,7 +36,12 @@
 
 	function show_box() {
 		// We have a potential problem here
-		submit.prop( 'disabled', true );
+		
+		// disable submit only if the box isn't already checked
+		if ( false === jQuery('#security-question input').is(':checked') ){
+			submit.prop( 'disabled', true );
+		}
+
 		if ( $( '#security-question' ).length !== 0 ) {
 			// We've already created the checkbox
 			$( '#security-question' ).show();