diff --git a/traitlets/config/loader.py b/traitlets/config/loader.py
index c389af17..f385226d 100644
--- a/traitlets/config/loader.py
+++ b/traitlets/config/loader.py
@@ -61,10 +61,12 @@ def print_help(self, file=None):
 # Config class for holding config information
 #-----------------------------------------------------------------------------
 
+
 def execfile(fname, glob):
     with open(fname, 'rb') as f:
         exec(compile(f.read(), fname, 'exec'), glob, glob)
 
+
 class LazyConfigValue(HasTraits):
     """Proxy object for exposing methods on configurable containers
 
@@ -82,6 +84,15 @@ class LazyConfigValue(HasTraits):
     _prepend = List()
     _inserts = List()
 
+    def __bool__(self):
+        # be falsy if we're empty
+        return bool(
+            self._extend
+            or self._prepend
+            or self._inserts
+            or self._update
+        )
+
     def append(self, obj):
         self._extend.append(obj)
 
@@ -92,7 +103,6 @@ def prepend(self, other):
         """like list.extend, but for the front"""
         self._prepend[:0] = other
 
-
     def merge_into(self, other):
         """
         Merge with another  earlier LazyConfig Value or an earlier container.
@@ -126,8 +136,6 @@ def merge_into(self, other):
             # other is a container, reify now.
             return self.get_value(other)
 
-
-
     def insert(self, index, other):
         if not isinstance(index, int):
             raise TypeError("An integer is required")
@@ -272,7 +280,15 @@ def __contains__(self, key):
                 return False
             return remainder in self[first]
 
-        return super(Config, self).__contains__(key)
+        if super(Config, self).__contains__(key):
+            item = self[key]
+            if isinstance(item, LazyConfigValue) and not item:
+                # don't consider empty lazy config present
+                # since it doesn't contain anything
+                return False
+            return True
+        return False
+
 
     # .has_key is deprecated for dictionaries.
     has_key = __contains__
@@ -345,6 +361,9 @@ def __delattr__(self, key):
         except KeyError as e:
             raise AttributeError(e)
 
+    def __repr__(self):
+        return 'Config('+super().__repr__()+')'
+
 
 #-----------------------------------------------------------------------------
 # Config loading classes
diff --git a/traitlets/config/tests/test_loader.py b/traitlets/config/tests/test_loader.py
index 4263fb66..0b6db8a2 100644
--- a/traitlets/config/tests/test_loader.py
+++ b/traitlets/config/tests/test_loader.py
@@ -485,7 +485,34 @@ def test_getattr_not_section(self):
         self.assertNotIn('foo', cfg)
         foo = cfg.foo
         assert isinstance(foo, LazyConfigValue)
-        self.assertIn('foo', cfg)
+        # empty lazy value indicates no config is actually there
+        assert 'foo' not in cfg
+        foo.append('x')
+        assert 'foo' in cfg
+
+    def test_lazy_truthiness(self):
+        cfg = Config()
+        lazy = cfg.empty_trait
+        assert not lazy
+        assert not cfg.empty_trait
+
+        cfg.append_trait.append('x')
+        assert cfg.append_trait
+
+        cfg.prepend_trait.prepend('x')
+        assert cfg.prepend_trait
+
+        cfg.extend_trait.extend(['x'])
+        assert cfg.extend_trait
+
+        cfg.Class.insert_trait.insert(0, 'x')
+        assert cfg.Class.insert_trait
+
+        cfg.Class.update_trait.update({'key': 'value'})
+        assert cfg.Class.update_trait
+
+        cfg.Class.add_trait.add('item')
+        assert cfg.Class.add_trait
 
     def test_getattr_private_missing(self):
         cfg = Config()
@@ -508,13 +535,15 @@ def test_lazy_config_repr(self):
         assert repr([0,1]) in repr2
         assert 'value=' in repr2
 
-
     def test_getitem_not_section(self):
         cfg = Config()
         self.assertNotIn('foo', cfg)
         foo = cfg['foo']
         assert isinstance(foo, LazyConfigValue)
-        self.assertIn('foo', cfg)
+        # empty lazy value indicates no config is actually there
+        assert 'foo' not in cfg
+        foo.append('x')
+        assert 'foo' in cfg
 
     def test_merge_no_copies(self):
         c = Config()
@@ -655,3 +684,18 @@ def test_merge_multi_lazy_update_III(self):
         c.merge(c2)
 
         self.assertEqual(c.Foo.trait._update, {"a": 1, "z": 26, "b": 1})
+
+    def test_empty_lazy_not_in(self):
+        c = Config()
+        lazy1 = c.Foo.trait
+        # 'in' check looks for *actual* config
+        # so creation of a lazy config handle
+        # doesn't mean we have config there
+        assert 'trait' not in c.Foo
+        # make sure that subsequent lazy access
+        # doesn't create a new LazyConfigValue, though
+        c.Foo.trait.append("x")
+        assert 'trait' in c.Foo
+        assert c.Foo.trait
+        assert lazy1 is c.Foo.trait
+        assert lazy1