diff --git c/ext/-test-/iter/break.c i/ext/-test-/iter/break.c
new file mode 100644
index 0000000..78c7da6
--- /dev/null
+++ i/ext/-test-/iter/break.c
@@ -0,0 +1,15 @@
+#include <ruby.h>
+
+static VALUE
+iter_break_value(VALUE self, VALUE val)
+{
+    rb_iter_break_value(val);
+    return self;		/* not reached */
+}
+
+void
+Init_break(void)
+{
+    VALUE breakable = rb_define_module_under(rb_define_module("Bug"), "Breakable");
+    rb_define_module_function(breakable, "iter_break", iter_break_value, 1);
+}
diff --git c/ext/-test-/iter/extconf.rb i/ext/-test-/iter/extconf.rb
new file mode 100644
index 0000000..695b5e9
--- /dev/null
+++ i/ext/-test-/iter/extconf.rb
@@ -0,0 +1 @@
+create_makefile("-test-/iter/break")
diff --git c/include/ruby/ruby.h i/include/ruby/ruby.h
index 200a648..753e374 100644
--- c/include/ruby/ruby.h
+++ i/include/ruby/ruby.h
@@ -1185,6 +1185,7 @@ NORETURN(void rb_bug_errno(const char*, int));
 NORETURN(void rb_sys_fail(const char*));
 NORETURN(void rb_mod_sys_fail(VALUE, const char*));
 NORETURN(void rb_iter_break(void));
+NORETURN(void rb_iter_break_value(VALUE));
 NORETURN(void rb_exit(int));
 NORETURN(void rb_notimplement(void));
 VALUE rb_syserr_new(int, const char *);
diff --git c/test/-ext-/iter/test_iter_break.rb i/test/-ext-/iter/test_iter_break.rb
new file mode 100644
index 0000000..5276653
--- /dev/null
+++ i/test/-ext-/iter/test_iter_break.rb
@@ -0,0 +1,8 @@
+require 'test/unit'
+require '-test-/iter/break'
+
+class TestIterBreak < Test::Unit::TestCase
+  def test_iter_break
+    assert_equal(42, 1.times{Bug::Breakable.iter_break(42)})
+  end
+end
diff --git c/vm.c i/vm.c
index 2cc8c5a..f8920bc 100644
--- c/vm.c
+++ i/vm.c
@@ -987,23 +987,29 @@ rb_vm_jump_tag_but_local_jump(int state, VALUE val)
     JUMP_TAG(state);
 }
 
-NORETURN(static void vm_iter_break(rb_thread_t *th));
+NORETURN(static void vm_iter_break(rb_thread_t *th, VALUE val));
 
 static void
-vm_iter_break(rb_thread_t *th)
+vm_iter_break(rb_thread_t *th, VALUE val)
 {
     rb_control_frame_t *cfp = th->cfp;
     VALUE *dfp = GC_GUARDED_PTR_REF(*cfp->dfp);
 
     th->state = TAG_BREAK;
-    th->errinfo = (VALUE)NEW_THROW_OBJECT(Qnil, (VALUE)dfp, TAG_BREAK);
+    th->errinfo = (VALUE)NEW_THROW_OBJECT(val, (VALUE)dfp, TAG_BREAK);
     TH_JUMP_TAG(th, TAG_BREAK);
 }
 
 void
 rb_iter_break(void)
 {
-    vm_iter_break(GET_THREAD());
+    vm_iter_break(GET_THREAD(), Qnil);
+}
+
+void
+rb_iter_break_value(VALUE val)
+{
+    vm_iter_break(GET_THREAD(), val);
 }
 
 /* optimization: redefine management */
@@ -1355,6 +1361,7 @@ vm_exec(rb_thread_t *th)
 #endif
 			}
 			th->errinfo = Qnil;
+			th->state = 0;
 			goto vm_loop_start;
 		    }
 		}
diff --git c/vm_eval.c i/vm_eval.c
index 7b37b10..0ee8179 100644
--- c/vm_eval.c
+++ i/vm_eval.c
@@ -906,6 +906,7 @@ rb_iterate(VALUE (* it_proc) (VALUE), VALUE data1,
 		state = 0;
 		th->state = 0;
 		th->errinfo = Qnil;
+		retval = GET_THROWOBJ_VAL(err);
 
 		/* check skipped frame */
 		while (th->cfp != cfp) {