diff -r b0087e17cd5e Lib/test/test_bytes.py
--- a/Lib/test/test_bytes.py	Fri Jul 01 17:57:30 2016 +0300
+++ b/Lib/test/test_bytes.py	Sat Jul 02 22:52:54 2016 +0300
@@ -1328,6 +1328,14 @@ class ByteArrayTest(BaseBytesTest, unitt
 
     test_exhausted_iterator = test.list_tests.CommonTest.test_exhausted_iterator
 
+    def test_iterator_length_hint(self):
+        ba = bytearray(b'ab')
+        it = iter(ba)
+        next(it)
+        ba.clear()
+        self.assertEqual(list(it), [])
+
+
 class AssortedBytesTest(unittest.TestCase):
     #
     # Test various combinations of bytes and bytearray
diff -r b0087e17cd5e Misc/NEWS
--- a/Misc/NEWS	Fri Jul 01 17:57:30 2016 +0300
+++ b/Misc/NEWS	Sat Jul 02 22:52:54 2016 +0300
@@ -10,6 +10,9 @@ What's New in Python 3.6.0 alpha 3
 Core and Builtins
 -----------------
 
+- Issue #XXXXX: __length_hint__() of bytearray itearator no longer return
+  negative integer for resized bytearray.
+
 - Issue #27007: The fromhex() class methods of bytes and bytearray subclasses
   now return an instance of corresponding subclass.
 
diff -r b0087e17cd5e Objects/bytearrayobject.c
--- a/Objects/bytearrayobject.c	Fri Jul 01 17:57:30 2016 +0300
+++ b/Objects/bytearrayobject.c	Sat Jul 02 22:52:54 2016 +0300
@@ -2248,8 +2248,12 @@ static PyObject *
 bytearrayiter_length_hint(bytesiterobject *it)
 {
     Py_ssize_t len = 0;
-    if (it->it_seq)
+    if (it->it_seq) {
         len = PyByteArray_GET_SIZE(it->it_seq) - it->it_index;
+        if (len < 0) {
+            len = 0;
+        }
+    }
     return PyLong_FromSsize_t(len);
 }