diff --git a/bison/__version__.py b/bison/__version__.py
index a6c7ca7..4196ea1 100644
--- a/bison/__version__.py
+++ b/bison/__version__.py
@@ -3,7 +3,7 @@
 __title__ = 'bison'
 __description__ = 'Python application configuration'
 __url__ = 'https://github.com/edaniszewski/bison'
-__version__ = '0.0.2'
+__version__ = '0.0.3'
 __author__ = 'Erick Daniszewski'
 __author_email__ = 'edaniszewski@gmail.com'
 __license__ = 'MIT'
diff --git a/bison/utils.py b/bison/utils.py
index 70db13e..f2065b9 100644
--- a/bison/utils.py
+++ b/bison/utils.py
@@ -62,8 +62,14 @@ class DotDict(dict):
         # otherwise, traverse the key components to set the value
         first, remainder = key.split('.', 1)
         if first in self:
-            v = super(DotDict, self).__getitem__(first)
-            v.__setitem__(remainder, value)
+            elem = super(DotDict, self).__getitem__(first)
+            if isinstance(elem, dict):
+                dd = DotDict(elem)
+                dd.__setitem__(remainder, value)
+                elem.update(dd)
+            else:
+                k, v = build_dot_value(key, value)
+                super(DotDict, self).__setitem__(k, v)
 
         else:
             k, v = build_dot_value(key, value)
diff --git a/tests/test_bison.py b/tests/test_bison.py
index a752a1f..377bff2 100644
--- a/tests/test_bison.py
+++ b/tests/test_bison.py
@@ -84,6 +84,33 @@ class TestBison:
         assert len(b._override) == 1
         assert b.get(key) == value
 
+    def test_set_multiple_nested(self):
+        """Set overrides for multiple nested values"""
+        b = bison.Bison()
+        assert len(b._override) == 0
+        assert len(b.config) == 0
+
+        b.set('foo.bar.a', 'test')
+
+        assert b.config == {
+            'foo': {
+                'bar': {
+                    'a': 'test'
+                }
+            }
+        }
+
+        b.set('foo.bar.b', 'test')
+
+        assert b.config == {
+            'foo': {
+                'bar': {
+                    'a': 'test',
+                    'b': 'test'
+                }
+            }
+        }
+
     @pytest.mark.parametrize(
         'paths', [
             (),
diff --git a/tests/test_utils.py b/tests/test_utils.py
index 4b4d5ee..fdd3fde 100644
--- a/tests/test_utils.py
+++ b/tests/test_utils.py
@@ -202,6 +202,168 @@ class TestDotDict:
         dd[key] = value
         assert dd.get(key) == value
 
+    def test_set_multiple_nested(self):
+        """Set multiple nested items"""
+        dd = utils.DotDict()
+        assert dd == {}
+
+        dd['foo.bar.a'] = 'test'
+        assert dd == {
+            'foo': {
+                'bar': {
+                    'a': 'test'
+                }
+            }
+        }
+
+        dd['foo.bar.b'] = 'test'
+        assert dd == {
+            'foo': {
+                'bar': {
+                    'a': 'test',
+                    'b': 'test'
+                }
+            }
+        }
+
+    def test_set_multiple_neste2(self):
+        """Set multiple nested items"""
+        dd = utils.DotDict()
+        assert dd == {}
+
+        dd['foo'] = 'test'
+        assert dd == {
+            'foo': 'test'
+        }
+
+        dd['bar.baz'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test'
+            }
+        }
+
+        dd['bar.ball'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test'
+            }
+        }
+
+        dd['bar.bits.a'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test',
+                'bits': {
+                    'a': 'test'
+                }
+            }
+        }
+
+        dd['bar.bits.b'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test',
+                'bits': {
+                    'a': 'test',
+                    'b': 'test'
+                }
+            }
+        }
+
+        dd['bar.new.a'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test',
+                'bits': {
+                    'a': 'test',
+                    'b': 'test'
+                },
+                'new': {
+                    'a': 'test'
+                }
+            }
+        }
+
+        dd['bar.new.b.c.d'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test',
+                'bits': {
+                    'a': 'test',
+                    'b': 'test'
+                },
+                'new': {
+                    'a': 'test',
+                    'b': {
+                        'c': {
+                            'd': 'test'
+                        }
+                    }
+                }
+            }
+        }
+
+        dd['bar.new.b'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': {
+                'baz': 'test',
+                'ball': 'test',
+                'bits': {
+                    'a': 'test',
+                    'b': 'test'
+                },
+                'new': {
+                    'a': 'test',
+                    'b': 'test'
+                }
+            }
+        }
+
+        dd['bar'] = 'test'
+        assert dd == {
+            'foo': 'test',
+            'bar': 'test'
+        }
+
+        dd['foo.bar.a'] = 'test'
+        assert dd == {
+            'foo': {
+                'bar': {
+                    'a': 'test'
+                }
+            },
+            'bar': 'test'
+        }
+
+        dd['foo'] = ['a', 'b', 'c']
+        assert dd == {
+            'foo': ['a', 'b', 'c'],
+            'bar': 'test'
+        }
+
+        dd['foo.bar.b'] = ['a', 'b', 'c']
+        assert dd == {
+            'foo': {
+                'bar': {
+                    'b': ['a', 'b', 'c']
+                }
+            },
+            'bar': 'test'
+        }
+
     @pytest.mark.parametrize(
         'key,expected', [
             ('a', True),