diff --git a/Lib/unittest/mock.py b/Lib/unittest/mock.py
index b1ab8631a422ef..2b9e7f14a75635 100644
--- a/Lib/unittest/mock.py
+++ b/Lib/unittest/mock.py
@@ -895,13 +895,20 @@ def assert_has_calls(self, calls, any_order=False):
         If `any_order` is True then the calls can be in any order, but
         they must all appear in `mock_calls`."""
         expected = [self._call_matcher(c) for c in calls]
-        cause = expected if isinstance(expected, Exception) else None
+        cause = next((e for e in expected if isinstance(e, Exception)), None)
         all_calls = _CallList(self._call_matcher(c) for c in self.mock_calls)
         if not any_order:
             if expected not in all_calls:
+                if cause is None:
+                    problem = 'Calls not found.'
+                else:
+                    problem = ('Error processing expected calls.\n'
+                               'Errors: {}').format(
+                                   [e if isinstance(e, Exception) else None
+                                    for e in expected])
                 raise AssertionError(
-                    'Calls not found.\nExpected: %r\n'
-                    'Actual: %r' % (_CallList(calls), self.mock_calls)
+                    '%s\nExpected: %r\nActual: %r' % (
+                        problem, _CallList(calls), self.mock_calls)
                 ) from cause
             return
 
diff --git a/Lib/unittest/test/testmock/testmock.py b/Lib/unittest/test/testmock/testmock.py
index 4e0f4694b77115..3046d4cfe63938 100644
--- a/Lib/unittest/test/testmock/testmock.py
+++ b/Lib/unittest/test/testmock/testmock.py
@@ -1,4 +1,5 @@
 import copy
+import re
 import sys
 import tempfile
 
@@ -1394,6 +1395,32 @@ def f(a, b, c, d=None):
             mock.assert_has_calls(calls[:-1])
         mock.assert_has_calls(calls[:-1], any_order=True)
 
+    def test_assert_has_calls_not_matching_spec_error(self):
+        def f(x=None): pass
+
+        mock = Mock(spec=f)
+        mock(1)
+
+        with self.assertRaisesRegex(
+                AssertionError,
+                '^{}$'.format(
+                    re.escape('Calls not found.\n'
+                              'Expected: [call()]\n'
+                              'Actual: [call(1)]'))) as cm:
+            mock.assert_has_calls([call()])
+        self.assertIsNone(cm.exception.__cause__)
+
+
+        with self.assertRaisesRegex(
+                AssertionError,
+                '^{}$'.format(
+                    re.escape(
+                        'Error processing expected calls.\n'
+                        "Errors: [None, TypeError('too many positional arguments')]\n"
+                        "Expected: [call(), call(1, 2)]\n"
+                        'Actual: [call(1)]'))) as cm:
+            mock.assert_has_calls([call(), call(1, 2)])
+        self.assertIsInstance(cm.exception.__cause__, TypeError)
 
     def test_assert_any_call(self):
         mock = Mock()
diff --git a/Misc/NEWS.d/next/Core and Builtins/2019-09-24-18-45-46.bpo-36871.p47knk.rst b/Misc/NEWS.d/next/Core and Builtins/2019-09-24-18-45-46.bpo-36871.p47knk.rst
new file mode 100644
index 00000000000000..56ee0f43f5d4c4
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2019-09-24-18-45-46.bpo-36871.p47knk.rst	
@@ -0,0 +1,3 @@
+Improve error handling for the assert_has_calls method of mocks.
+Fixed a bug where any errors encountered while binding the expected calls
+to the mock's spec were silently swallowed, leading to misleading error output.