diff --git a/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl b/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
index 31c3883cbf..35fd0e5bcf 100644
--- a/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
+++ b/pkgs/racket-pkgs/racket-test/tests/racket/optimize.rktl
@@ -1328,6 +1328,18 @@
                              (a1)
                              (a2))))
 
+(test-comp '(if (let ([z (random)]) null) 1 2)
+           '(if (let ([z (random)]) #t) 1 2))
+
+(test-comp '(if (if (list? (cons 1 null)) null (void)) 1 2)
+           '1)
+
+(test-comp '(if (if (list? (cons 1 null)) 7 8) 1 2)
+           '1)
+
+(test-comp '(if (if (list? (cons 1 null)) #t #t) 1 2)
+           '1)
+
 (test-comp '(lambda (y)
               (let ([f (lambda (x) x)])
                 (if f
diff --git a/racket/src/racket/src/optimize.c b/racket/src/racket/src/optimize.c
index 91a3877fef..c913239d4b 100644
--- a/racket/src/racket/src/optimize.c
+++ b/racket/src/racket/src/optimize.c
@@ -6409,7 +6409,12 @@ Scheme_Object *scheme_optimize_expr(Scheme_Object *expr, Optimize_Info *info, in
     return module_optimize(expr, info, context);
   default:
     info->size += 1;
-    return expr;
+    if ((context & OPT_CONTEXT_BOOLEAN)
+        && (SCHEME_TYPE(expr) > _scheme_compiled_values_types_)
+        && SCHEME_TRUEP(expr))
+      return scheme_true;
+    else
+      return expr;
   }
 }