diff --git a/PIL/IcoImagePlugin.py b/PIL/IcoImagePlugin.py
index b278a85bf07..3436ae84f49 100644
--- a/PIL/IcoImagePlugin.py
+++ b/PIL/IcoImagePlugin.py
@@ -44,16 +44,19 @@ def _save(im, fp, filename):
     fp.write(_MAGIC)  # (2+2)
     sizes = im.encoderinfo.get("sizes",
                                [(16, 16), (24, 24), (32, 32), (48, 48),
-                                (64, 64), (128, 128), (255, 255)])
+                                (64, 64), (128, 128), (256, 256)])
     width, height = im.size
-    filter(lambda x: False if (x[0] > width or x[1] > height or
-                               x[0] > 255 or x[1] > 255) else True, sizes)
+    sizes = filter(lambda x: False if (x[0] > width or x[1] > height or
+                                       x[0] > 256 or x[1] > 256) else True,
+                   sizes)
+    sizes = list(sizes)
     fp.write(struct.pack("<H", len(sizes)))  # idCount(2)
     offset = fp.tell() + len(sizes)*16
     for size in sizes:
         width, height = size
-        fp.write(struct.pack("B", width))  # bWidth(1)
-        fp.write(struct.pack("B", height))  # bHeight(1)
+        # 0 means 256
+        fp.write(struct.pack("B", width if width < 256 else 0))  # bWidth(1)
+        fp.write(struct.pack("B", height if height < 256 else 0))  # bHeight(1)
         fp.write(b"\0")  # bColorCount(1)
         fp.write(b"\0")  # bReserved(1)
         fp.write(b"\0\0")  # wPlanes(2)
@@ -215,13 +218,13 @@ def frame(self, idx):
                 total_bytes = int((w * im.size[1]) / 8)
 
                 self.buf.seek(and_mask_offset)
-                maskData = self.buf.read(total_bytes)
+                mask_data = self.buf.read(total_bytes)
 
                 # convert raw data to image
                 mask = Image.frombuffer(
                     '1',            # 1 bpp
                     im.size,        # (w, h)
-                    maskData,       # source chars
+                    mask_data,      # source chars
                     'raw',          # raw decoder
                     ('1;I', int(w/8), -1)  # 1bpp inverted, padded, reversed
                 )
@@ -278,6 +281,7 @@ def load_seek(self):
 #
 # --------------------------------------------------------------------
 
+
 Image.register_open(IcoImageFile.format, IcoImageFile, _accept)
 Image.register_save(IcoImageFile.format, _save)
 Image.register_extension(IcoImageFile.format, ".ico")
diff --git a/Tests/images/hopper_256x256.ico b/Tests/images/hopper_256x256.ico
new file mode 100644
index 00000000000..2c08b1f3cf7
Binary files /dev/null and b/Tests/images/hopper_256x256.ico differ
diff --git a/Tests/test_file_ico.py b/Tests/test_file_ico.py
index 94b8c44e3fc..3904340f3a0 100644
--- a/Tests/test_file_ico.py
+++ b/Tests/test_file_ico.py
@@ -48,6 +48,37 @@ def test_save_to_bytes(self):
         self.assert_image_equal(reloaded,
                                 hopper().resize((32, 32), Image.LANCZOS))
 
+    def test_save_256x256(self):
+        """Issue #2264 https://github.com/python-pillow/Pillow/issues/2264"""
+        # Arrange
+        im = Image.open("Tests/images/hopper_256x256.ico")
+        outfile = self.tempfile("temp_saved_hopper_256x256.ico")
+
+        # Act
+        im.save(outfile)
+        im_saved = Image.open(outfile)
+
+        # Assert
+        self.assertEqual(im_saved.size, (256, 256))
+
+    def test_only_save_relevant_sizes(self):
+        """Issue #2266 https://github.com/python-pillow/Pillow/issues/2266
+        Should save in 16x16, 24x24, 32x32, 48x48 sizes
+        and not in 16x16, 24x24, 32x32, 48x48, 48x48, 48x48, 48x48 sizes
+        """
+        # Arrange
+        im = Image.open("Tests/images/python.ico")  # 16x16, 32x32, 48x48
+        outfile = self.tempfile("temp_saved_python.ico")
+
+        # Act
+        im.save(outfile)
+        im_saved = Image.open(outfile)
+
+        # Assert
+        self.assertEqual(
+            im_saved.info['sizes'],
+            set([(16, 16), (24, 24), (32, 32), (48, 48)]))
+
 
 if __name__ == '__main__':
     unittest.main()