diff --git a/Lib/test/test_site.py b/Lib/test/test_site.py
index 4e801e9..0f8405a 100644
--- a/Lib/test/test_site.py
+++ b/Lib/test/test_site.py
@@ -6,6 +6,7 @@
 """
 import unittest
 from test.test_support import run_unittest, TESTFN, EnvironmentVarGuard
+from test.test_support import captured_output
 import __builtin__
 import os
 import sys
@@ -94,6 +95,53 @@
         finally:
             pth_file.cleanup()
 
+    def make_pth(self, contents, pth_dir='.', pth_name=TESTFN):
+        # Create a .pth file and return its (abspath, basename).
+        pth_dir = os.path.abspath(pth_dir)
+        pth_basename = pth_name + '.pth'
+        pth_fn = os.path.join(pth_dir, pth_basename)
+        pth_file = open(pth_fn, 'w')
+        self.addCleanup(lambda: os.remove(pth_fn))
+        pth_file.write(contents)
+        pth_file.close()
+        return pth_dir, pth_basename
+
+    def test_addpackage_import_bad_syntax(self):
+        # Issue 10642
+        pth_dir, pth_fn = self.make_pth("import bad)syntax\n")
+        with captured_output("stderr") as err_out:
+            site.addpackage(pth_dir, pth_fn, set())
+        self.assertRegexpMatches(err_out.getvalue(), "line 1")
+        self.assertRegexpMatches(err_out.getvalue(), os.path.join(pth_dir, pth_fn))
+        # XXX: the previous two should be independent checks so that the
+        # order doesn't matter.  The next three could be a single check
+        # but my regex foo isn't good enough to write it.
+        self.assertRegexpMatches(err_out.getvalue(), 'Traceback')
+        self.assertRegexpMatches(err_out.getvalue(), r'import bad\)syntax')
+        self.assertRegexpMatches(err_out.getvalue(), 'SyntaxError')
+
+    def test_addpackage_import_bad_exec(self):
+        # Issue 10642
+        pth_dir, pth_fn = self.make_pth("randompath\nimport nosuchmodule\n")
+        with captured_output("stderr") as err_out:
+            site.addpackage(pth_dir, pth_fn, set())
+        self.assertRegexpMatches(err_out.getvalue(), "line 2")
+        self.assertRegexpMatches(err_out.getvalue(), os.path.join(pth_dir, pth_fn))
+        # XXX: ditto previous XXX comment.
+        self.assertRegexpMatches(err_out.getvalue(), 'Traceback')
+        self.assertRegexpMatches(err_out.getvalue(), 'ImportError')
+
+    def test_addpackage_import_bad_pth_file(self):
+        # Issue 5258
+        pth_dir, pth_fn = self.make_pth("abc\x00def\n")
+        with captured_output("stderr") as err_out:
+            site.addpackage(pth_dir, pth_fn, set())
+        self.assertRegexpMatches(err_out.getvalue(), "line 1")
+        self.assertRegexpMatches(err_out.getvalue(), os.path.join(pth_dir, pth_fn))
+        # XXX: ditto previous XXX comment.
+        self.assertRegexpMatches(err_out.getvalue(), 'Traceback')
+        self.assertRegexpMatches(err_out.getvalue(), 'TypeError')
+
     def test_addsitedir(self):
         # Same tests for test_addpackage since addsitedir() essentially just
         # calls addpackage() for every .pth file in the directory