diff --git a/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl b/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
index 2e98e73706..26c003c6b2 100644
--- a/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
+++ b/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
@@ -1335,6 +1335,9 @@
                 (quote-syntax no!))
            ''ok)
 
+(test-comp '(lambda (x) (not (if x #f 2)))
+           '(lambda (x) (not (if x #f #t))))
+
 (test-comp '(lambda (x) (if x x #f))
            '(lambda (x) x))
 (test-comp '(lambda (x) (if (cons 1 x) 78 78))
diff --git a/racket/src/racket/src/optimize.c b/racket/src/racket/src/optimize.c
index 17178702cf..529152b012 100644
--- a/racket/src/racket/src/optimize.c
+++ b/racket/src/racket/src/optimize.c
@@ -2724,7 +2724,7 @@ static Scheme_Object *optimize_application2(Scheme_Object *o, Optimize_Info *inf
   if (le)
     return le;
 
-  le = scheme_optimize_expr(app->rator, info, sub_context);
+  le = scheme_optimize_expr(app->rator, info, 0);
   app->rator = le;
 
   {
@@ -2734,9 +2734,13 @@ static Scheme_Object *optimize_application2(Scheme_Object *o, Optimize_Info *inf
       return le;
   }
 
-  ty = wants_local_type_arguments(app->rator, 0);
-  if (ty)
-    sub_context |= (ty << OPT_CONTEXT_TYPE_SHIFT);
+  if (SAME_PTR(scheme_not_prim, app->rator)){
+    sub_context = OPT_CONTEXT_BOOLEAN;
+  } else {
+    ty = wants_local_type_arguments(app->rator, 0);
+    if (ty)
+      sub_context |= (ty << OPT_CONTEXT_TYPE_SHIFT);
+  }
 
   le = scheme_optimize_expr(app->rand, info, sub_context);
   app->rand = le;