diff --git a/fmutils.go b/fmutils.go
index 81e08b3..2f5d101 100644
--- a/fmutils.go
+++ b/fmutils.go
@@ -183,14 +183,22 @@ func (mask NestedMask) overwrite(srcRft, destRft protoreflect.Message) {
 		} else if srcFD.IsMap() && srcFD.Kind() == protoreflect.MessageKind {
 			srcMap := srcRft.Get(srcFD).Map()
 			destMap := destRft.Get(srcFD).Map()
+			if !destMap.IsValid() {
+				destRft.Set(srcFD, protoreflect.ValueOf(srcMap))
+				destMap = destRft.Get(srcFD).Map()
+			}
 			srcMap.Range(func(mk protoreflect.MapKey, mv protoreflect.Value) bool {
 				if mi, ok := submask[mk.String()]; ok {
 					if i, ok := mv.Interface().(protoreflect.Message); ok && len(mi) > 0 {
-						destMap.Set(mk, mv)
-						mi.overwrite(i, mv.Message())
+						newVal := protoreflect.ValueOf(i.New())
+						destMap.Set(mk, newVal)
+						mi.overwrite(mv.Message(), newVal.Message())
 					} else {
+
 						destMap.Set(mk, mv)
 					}
+				} else {
+					destMap.Clear(mk)
 				}
 				return true
 			})
diff --git a/fmutils_test.go b/fmutils_test.go
index e655687..3953d5f 100644
--- a/fmutils_test.go
+++ b/fmutils_test.go
@@ -885,7 +885,7 @@ func TestOverwrite(t *testing.T) {
 		},
 		{
 			name:  "overwrite map with message values",
-			paths: []string{"attributes.src1.tags", "attributes.src2.tags"},
+			paths: []string{"attributes.src1.tags.key1", "attributes.src2"},
 			src: &testproto.Profile{
 				User: nil,
 				Attributes: map[string]*testproto.Attribute{
@@ -903,7 +903,7 @@ func TestOverwrite(t *testing.T) {
 				},
 				Attributes: map[string]*testproto.Attribute{
 					"dest1": {
-						Tags: map[string]string{"key4": "value5"},
+						Tags: map[string]string{"key4": "value4"},
 					},
 				},
 			},
@@ -913,13 +913,13 @@ func TestOverwrite(t *testing.T) {
 				},
 				Attributes: map[string]*testproto.Attribute{
 					"src1": {
-						Tags: map[string]string{"key1": "value1", "key2": "value2"},
+						Tags: map[string]string{"key1": "value1"},
 					},
 					"src2": {
 						Tags: map[string]string{"key3": "value3"},
 					},
 					"dest1": {
-						Tags: map[string]string{"key4": "value5"},
+						Tags: map[string]string{"key4": "value4"},
 					},
 				},
 			},
@@ -1037,6 +1037,63 @@ func TestOverwrite(t *testing.T) {
 				},
 			},
 		},
+		{
+			name:  "overwrite repeated message fields to empty list",
+			paths: []string{"gallery.path"},
+			src: &testproto.Profile{
+				User: &testproto.User{
+					UserId: 567,
+					Name:   "different-name",
+				},
+				Photo: &testproto.Photo{
+					Path: "photo-path",
+				},
+				LoginTimestamps: []int64{1, 2, 3},
+				Attributes: map[string]*testproto.Attribute{
+					"src": {},
+				},
+				Gallery: []*testproto.Photo{
+					{
+						PhotoId: 123,
+						Path:    "test-path-1",
+						Dimensions: &testproto.Dimensions{
+							Width:  345,
+							Height: 456,
+						},
+					},
+					{
+						PhotoId: 234,
+						Path:    "test-path-2",
+						Dimensions: &testproto.Dimensions{
+							Width:  3456,
+							Height: 4567,
+						},
+					},
+					{
+						PhotoId: 345,
+						Path:    "test-path-3",
+						Dimensions: &testproto.Dimensions{
+							Width:  34567,
+							Height: 45678,
+						},
+					},
+				},
+			},
+			dest: &testproto.Profile{},
+			want: &testproto.Profile{
+				Gallery: []*testproto.Photo{
+					{
+						Path: "test-path-1",
+					},
+					{
+						Path: "test-path-2",
+					},
+					{
+						Path: "test-path-3",
+					},
+				},
+			},
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {