diff --git a/src/vm.c b/src/vm.c
index 8075a6e6e..12ee4aa9e 100644
--- a/src/vm.c
+++ b/src/vm.c
@@ -1721,7 +1721,7 @@ RETRY_TRY_BLOCK:
         if (irep->clen > 0 &&
             (ch = catch_handler_find(irep, ci->pc, MRB_CATCH_FILTER_ENSURE))) {
           /* avoiding a jump from a catch handler into the same handler */
-          if (a < mrb_irep_catch_handler_unpack(ch->begin) || a >= mrb_irep_catch_handler_unpack(ch->end)) {
+          if (a < mrb_irep_catch_handler_unpack(ch->begin) || a > mrb_irep_catch_handler_unpack(ch->end)) {
             THROW_TAGGED_BREAK(mrb, RBREAK_TAG_JUMP, mrb->c->ci, mrb_fixnum_value(a));
           }
         }
diff --git a/test/t/syntax.rb b/test/t/syntax.rb
index dedbbd1c2..f26bc1c52 100644
--- a/test/t/syntax.rb
+++ b/test/t/syntax.rb
@@ -71,6 +71,63 @@ assert('break', '11.5.2.4.3') do
     end
   end
   assert_equal [1,2,3,4], a
+
+  a = []
+  begin
+    while true
+      a.push 1
+      break
+      a.push "NG"
+    end
+  ensure
+    a.push 2
+  end
+  assert_equal [1, 2], a
+
+  a = []
+  begin
+    while true
+      a.push 1
+      break
+    end
+    a.push 2
+  ensure
+    a.push 3
+  end
+  assert_equal [1, 2, 3], a
+
+  a = []
+  begin
+    while true
+      begin
+        a.push 1
+        break
+      ensure
+        a.push 2
+      end
+      a.push "NG"
+    end
+  ensure
+    a.push 3
+  end
+  assert_equal [1, 2, 3], a
+
+  a = []
+  begin
+    while true
+      begin
+        a.push 1
+        break
+      ensure
+        a.push 2
+      end
+      a.push "NG"
+    end
+    a.push 3
+  ensure
+    a.push 4
+  end
+  assert_equal [1, 2, 3, 4], a
 end
 
 assert('redo', '11.5.2.4.5') do