diff --git a/Lib/test/regrtest.py b/Lib/test/regrtest.py
--- a/Lib/test/regrtest.py
+++ b/Lib/test/regrtest.py
@@ -662,20 +662,6 @@
         print(count(len(skipped), "test"), "skipped:")
         printlist(skipped)
 
-        e = _ExpectedSkips()
-        plat = sys.platform
-        if e.isvalid():
-            surprise = set(skipped) - e.getexpected() - set(resource_denieds)
-            if surprise:
-                print(count(len(surprise), "skip"), \
-                      "unexpected on", plat + ":")
-                printlist(surprise)
-            else:
-                print("Those skips are all expected on", plat + ".")
-        else:
-            print("Ask someone to teach regrtest.py about which tests are")
-            print("expected to get skipped on", plat + ".")
-
     if verbose2 and bad:
         print("Re-running failed tests in verbose mode")
         for test in bad:
@@ -1211,293 +1197,6 @@
     print(fill(' '.join(str(elt) for elt in sorted(x)), width,
                initial_indent=blanks, subsequent_indent=blanks))
 
-# Map sys.platform to a string containing the basenames of tests
-# expected to be skipped on that platform.
-#
-# Special cases:
-#     test_pep277
-#         The _ExpectedSkips constructor adds this to the set of expected
-#         skips if not os.path.supports_unicode_filenames.
-#     test_timeout
-#         Controlled by test_timeout.skip_expected.  Requires the network
-#         resource and a socket module.
-#
-# Tests that are expected to be skipped everywhere except on one platform
-# are also handled separately.
-
-_expectations = {
-    'win32':
-        """
-        test__locale
-        test_crypt
-        test_curses
-        test_dbm
-        test_fcntl
-        test_fork1
-        test_epoll
-        test_dbm_gnu
-        test_dbm_ndbm
-        test_grp
-        test_ioctl
-        test_largefile
-        test_kqueue
-        test_openpty
-        test_ossaudiodev
-        test_pipes
-        test_poll
-        test_posix
-        test_pty
-        test_pwd
-        test_resource
-        test_signal
-        test_syslog
-        test_threadsignals
-        test_wait3
-        test_wait4
-        """,
-    'linux2':
-        """
-        test_curses
-        test_largefile
-        test_kqueue
-        test_ossaudiodev
-        """,
-    'unixware7':
-        """
-        test_epoll
-        test_largefile
-        test_kqueue
-        test_minidom
-        test_openpty
-        test_pyexpat
-        test_sax
-        test_sundry
-        """,
-    'openunix8':
-        """
-        test_epoll
-        test_largefile
-        test_kqueue
-        test_minidom
-        test_openpty
-        test_pyexpat
-        test_sax
-        test_sundry
-        """,
-    'sco_sv3':
-        """
-        test_asynchat
-        test_fork1
-        test_epoll
-        test_gettext
-        test_largefile
-        test_locale
-        test_kqueue
-        test_minidom
-        test_openpty
-        test_pyexpat
-        test_queue
-        test_sax
-        test_sundry
-        test_thread
-        test_threaded_import
-        test_threadedtempfile
-        test_threading
-        """,
-    'darwin':
-        """
-        test__locale
-        test_curses
-        test_epoll
-        test_dbm_gnu
-        test_gdb
-        test_largefile
-        test_locale
-        test_minidom
-        test_ossaudiodev
-        test_poll
-        """,
-    'sunos5':
-        """
-        test_curses
-        test_dbm
-        test_epoll
-        test_kqueue
-        test_dbm_gnu
-        test_gzip
-        test_openpty
-        test_zipfile
-        test_zlib
-        """,
-    'hp-ux11':
-        """
-        test_curses
-        test_epoll
-        test_dbm_gnu
-        test_gzip
-        test_largefile
-        test_locale
-        test_kqueue
-        test_minidom
-        test_openpty
-        test_pyexpat
-        test_sax
-        test_zipfile
-        test_zlib
-        """,
-    'cygwin':
-        """
-        test_curses
-        test_dbm
-        test_epoll
-        test_ioctl
-        test_kqueue
-        test_largefile
-        test_locale
-        test_ossaudiodev
-        test_socketserver
-        """,
-    'os2emx':
-        """
-        test_audioop
-        test_curses
-        test_epoll
-        test_kqueue
-        test_largefile
-        test_mmap
-        test_openpty
-        test_ossaudiodev
-        test_pty
-        test_resource
-        test_signal
-        """,
-    'freebsd4':
-        """
-        test_epoll
-        test_dbm_gnu
-        test_locale
-        test_ossaudiodev
-        test_pep277
-        test_pty
-        test_socketserver
-        test_tcl
-        test_tk
-        test_ttk_guionly
-        test_ttk_textonly
-        test_timeout
-        test_urllibnet
-        test_multiprocessing
-        """,
-    'aix5':
-        """
-        test_bz2
-        test_epoll
-        test_dbm_gnu
-        test_gzip
-        test_kqueue
-        test_ossaudiodev
-        test_tcl
-        test_tk
-        test_ttk_guionly
-        test_ttk_textonly
-        test_zipimport
-        test_zlib
-        """,
-    'openbsd3':
-        """
-        test_ctypes
-        test_epoll
-        test_dbm_gnu
-        test_locale
-        test_normalization
-        test_ossaudiodev
-        test_pep277
-        test_tcl
-        test_tk
-        test_ttk_guionly
-        test_ttk_textonly
-        test_multiprocessing
-        """,
-    'netbsd3':
-        """
-        test_ctypes
-        test_curses
-        test_epoll
-        test_dbm_gnu
-        test_locale
-        test_ossaudiodev
-        test_pep277
-        test_tcl
-        test_tk
-        test_ttk_guionly
-        test_ttk_textonly
-        test_multiprocessing
-        """,
-}
-_expectations['freebsd5'] = _expectations['freebsd4']
-_expectations['freebsd6'] = _expectations['freebsd4']
-_expectations['freebsd7'] = _expectations['freebsd4']
-_expectations['freebsd8'] = _expectations['freebsd4']
-
-class _ExpectedSkips:
-    def __init__(self):
-        import os.path
-        from test import test_timeout
-
-        self.valid = False
-        if sys.platform in _expectations:
-            s = _expectations[sys.platform]
-            self.expected = set(s.split())
-
-            # These are broken tests, for now skipped on every platform.
-            # XXX Fix these!
-            self.expected.add('test_nis')
-
-            # expected to be skipped on every platform, even Linux
-            if not os.path.supports_unicode_filenames:
-                self.expected.add('test_pep277')
-
-            # doctest, profile and cProfile tests fail when the codec for the
-            # fs encoding isn't built in because PyUnicode_Decode() adds two
-            # calls into Python.
-            encs = ("utf-8", "latin-1", "ascii", "mbcs", "utf-16", "utf-32")
-            if sys.getfilesystemencoding().lower() not in encs:
-                self.expected.add('test_profile')
-                self.expected.add('test_cProfile')
-                self.expected.add('test_doctest')
-
-            if test_timeout.skip_expected:
-                self.expected.add('test_timeout')
-
-            if sys.platform != "win32":
-                # test_sqlite is only reliable on Windows where the library
-                # is distributed with Python
-                WIN_ONLY = {"test_unicode_file", "test_winreg",
-                            "test_winsound", "test_startfile",
-                            "test_sqlite"}
-                self.expected |= WIN_ONLY
-
-            if sys.platform != 'sunos5':
-                self.expected.add('test_nis')
-
-            if support.python_is_optimized():
-                self.expected.add("test_gdb")
-
-            self.valid = True
-
-    def isvalid(self):
-        "Return true iff _ExpectedSkips knows about the current platform."
-        return self.valid
-
-    def getexpected(self):
-        """Return set of test names we expect to skip on current platform.
-
-        self.isvalid() must be true.
-        """
-
-        assert self.isvalid()
-        return self.expected
-
 def _make_temp_dir_for_build(TEMPDIR):
     # When tests are run from the Python build directory, it is best practice
     # to keep the test files in a subfolder.  It eases the cleanup of leftover
diff --git a/Lib/test/support.py b/Lib/test/support.py
--- a/Lib/test/support.py
+++ b/Lib/test/support.py
@@ -75,17 +75,53 @@
         yield
 
 
-def import_module(name, deprecated=False):
+def import_module(name, deprecated=False, *, optional=[], required_on=[]):
     """Import and return the module to be tested, raising SkipTest if
     it is not available.
 
     If deprecated is True, any module or package deprecation messages
-    will be suppressed."""
+    will be suppressed.
+
+    If sys.platform or os.name is listed in required_on then the ImportError
+    is propagated instead of SkipTest. The opposite is true for 'optional'.
+    Use of 'optional' is always preferred as it is better to have to actively
+    list a platform a test is expected to be skipped on, i.e., whitelist vs.
+    blacklist.
+
+    Known sys.platform values are:
+
+        * win32
+        * linux2
+        * unixware7
+        * openunix8
+        * sco_sv3
+        * darwin
+        * sunos5
+        * hp-ux11
+        * cygwin
+        * os2emx
+        * freebsd4
+        * freebsd5
+        * freebsd6
+        * freebsd7
+        * freebsd8
+        * aix5
+        * openbsd3
+        * netbsd3
+
+    """
     with _ignore_deprecated_imports(deprecated):
         try:
             return importlib.import_module(name)
-        except ImportError as msg:
-            raise unittest.SkipTest(str(msg))
+        except ImportError as import_exc:
+            msg = '{0!r} not available'.format(name)
+            if required_on:
+                if sys.platform in required_on or os.name in required_on:
+                    raise
+            elif optional:
+                if sys.platform not in optional and os.name not in optional:
+                    raise
+            raise unittest.SkipTest(msg) from import_exc
 
 
 def _save_and_remove_module(name, orig_modules):
diff --git a/Lib/test/test_cprofile.py b/Lib/test/test_cprofile.py
--- a/Lib/test/test_cprofile.py
+++ b/Lib/test/test_cprofile.py
@@ -31,6 +31,12 @@
 
 
 def test_main():
+    import _codecs
+    codec_name = sys.getfilesystemencoding().lower().replace('-', '_')
+    fxn_name = codec_name + '_decode'
+    if not hasattr(_codecs,  fxn_name):
+        msg = 'FS encoding needs to be from _codecs to prevent false-negative'
+        raise unittest.SkipTest(msg)
     run_unittest(CProfileTest)
 
 def main():
diff --git a/Lib/test/test_crypt.py b/Lib/test/test_crypt.py
--- a/Lib/test/test_crypt.py
+++ b/Lib/test/test_crypt.py
@@ -1,7 +1,7 @@
 from test import support
 import unittest
 
-crypt = support.import_module('crypt')
+crypt = support.import_module('crypt', optional=['win32'])
 
 class CryptTestCase(unittest.TestCase):
 
diff --git a/Lib/test/test_ctypes.py b/Lib/test/test_ctypes.py
--- a/Lib/test/test_ctypes.py
+++ b/Lib/test/test_ctypes.py
@@ -3,7 +3,7 @@
 from test.support import run_unittest, import_module
 
 # Skip tests if _ctypes module was not built.
-import_module('_ctypes')
+import_module('_ctypes', optional=['openbsd3', 'netbsd3'])
 
 import ctypes.test
 
diff --git a/Lib/test/test_doctest.py b/Lib/test/test_doctest.py
--- a/Lib/test/test_doctest.py
+++ b/Lib/test/test_doctest.py
@@ -2474,6 +2474,12 @@
 ######################################################################
 
 def test_main():
+    import _codecs
+    codec_name = sys.getfilesystemencoding().lower().replace('-', '_')
+    fxn_name = codec_name + '_decode'
+    if not hasattr(_codecs,  fxn_name):
+        msg = 'FS encoding needs to be from _codecs to prevent false-negative'
+        raise unittest.SkipTest(msg)
     # Check the doctest cases in doctest itself:
     support.run_doctest(doctest, verbosity=True)
     # Check the doctest cases defined here:
diff --git a/Lib/test/test_fcntl.py b/Lib/test/test_fcntl.py
--- a/Lib/test/test_fcntl.py
+++ b/Lib/test/test_fcntl.py
@@ -10,7 +10,7 @@
 from test.support import verbose, TESTFN, unlink, run_unittest, import_module
 
 # Skip test if no fnctl module.
-fcntl = import_module('fcntl')
+fcntl = import_module('fcntl', optional=['win32'])
 
 
 # TODO - Write tests for flock() and lockf().
diff --git a/Lib/test/test_grp.py b/Lib/test/test_grp.py
--- a/Lib/test/test_grp.py
+++ b/Lib/test/test_grp.py
@@ -3,7 +3,8 @@
 import unittest
 from test import support
 
-grp = support.import_module('grp')
+grp = support.import_module('grp', optional=['win32'])
+
 
 class GroupDatabaseTestCase(unittest.TestCase):
 
diff --git a/Lib/test/test_nis.py b/Lib/test/test_nis.py
--- a/Lib/test/test_nis.py
+++ b/Lib/test/test_nis.py
@@ -3,7 +3,7 @@
 import sys
 
 # Skip test if nis module does not exist.
-nis = support.import_module('nis')
+nis = support.import_module('nis', optional=['win32'])
 
 
 class NisTests(unittest.TestCase):
diff --git a/Lib/test/test_pipes.py b/Lib/test/test_pipes.py
--- a/Lib/test/test_pipes.py
+++ b/Lib/test/test_pipes.py
@@ -1,11 +1,10 @@
-import pipes
 import os
 import string
 import unittest
-from test.support import TESTFN, run_unittest, unlink, reap_children
+from test.support import (TESTFN, run_unittest, unlink, reap_children,
+                            import_module)
 
-if os.name != 'posix':
-    raise unittest.SkipTest('pipes module only works on posix')
+pipes = import_module('pipes', required_on=['posix'])
 
 TESTFN2 = TESTFN + "2"
 
diff --git a/Lib/test/test_posix.py b/Lib/test/test_posix.py
--- a/Lib/test/test_posix.py
+++ b/Lib/test/test_posix.py
@@ -3,7 +3,7 @@
 from test import support
 
 # Skip these tests if there is no posix module.
-posix = support.import_module('posix')
+posix = support.import_module('posix', required_on=['posix'])
 
 import errno
 import sys
diff --git a/Lib/test/test_profile.py b/Lib/test/test_profile.py
--- a/Lib/test/test_profile.py
+++ b/Lib/test/test_profile.py
@@ -97,6 +97,12 @@
 
 
 def test_main():
+    import _codecs
+    codec_name = sys.getfilesystemencoding().lower().replace('-', '_')
+    fxn_name = codec_name + '_decode'
+    if not hasattr(_codecs,  fxn_name):
+        msg = 'FS encoding needs to be from _codecs to prevent false-negative'
+        raise unittest.SkipTest(msg)
     run_unittest(ProfileTest)
 
 def main():
diff --git a/Lib/test/test_pty.py b/Lib/test/test_pty.py
--- a/Lib/test/test_pty.py
+++ b/Lib/test/test_pty.py
@@ -3,6 +3,9 @@
 #Skip these tests if either fcntl or termios is not available
 fcntl = import_module('fcntl')
 import_module('termios')
+pty = import_module('pty',
+            optional=['win32', 'os2emx', 'freebsd4', 'freebsd5', 'freebsd6',
+                        'freebsd7', 'freebsd8'])
 
 import errno
 import pty
diff --git a/Lib/test/test_pwd.py b/Lib/test/test_pwd.py
--- a/Lib/test/test_pwd.py
+++ b/Lib/test/test_pwd.py
@@ -2,7 +2,7 @@
 import unittest
 from test import support
 
-pwd = support.import_module('pwd')
+pwd = support.import_module('pwd', optional=['win32'])
 
 class PwdTest(unittest.TestCase):
 
diff --git a/Lib/test/test_resource.py b/Lib/test/test_resource.py
--- a/Lib/test/test_resource.py
+++ b/Lib/test/test_resource.py
@@ -2,7 +2,8 @@
 from test import support
 import time
 
-resource = support.import_module('resource')
+resource = support.import_module('resource', optional=['win32'])
+
 
 # This test is checking a few specific problem spots with the resource module.
 
diff --git a/Lib/test/test_sqlite.py b/Lib/test/test_sqlite.py
--- a/Lib/test/test_sqlite.py
+++ b/Lib/test/test_sqlite.py
@@ -1,7 +1,7 @@
 import test.support
 
 # Skip test if _sqlite3 module not installed
-test.support.import_module('_sqlite3')
+test.support.import_module('_sqlite3', required_on=['win32'])
 
 import sqlite3
 from sqlite3.test import (dbapi, types, userfunctions,
diff --git a/Lib/test/test_support.py b/Lib/test/test_support.py
new file mode 100644
--- /dev/null
+++ b/Lib/test/test_support.py
@@ -0,0 +1,42 @@
+from test import support
+import os
+import sys
+import unittest
+
+
+class import_module_Tests(unittest.TestCase):
+
+    nonexistent_name = "asdfasdfasdflaksdfasdfasdlfjasdflkjas;lfjsadklf"
+
+    def test_skipping(self):
+        with self.assertRaises(unittest.SkipTest):
+            support.import_module(self.nonexistent_name)
+
+    def test_requiring_on(self):
+        # sys.platform and os.name are both supported.
+        for require in (sys.platform, os.name):
+            with self.assertRaises(ImportError):
+                support.import_module(self.nonexistent_name,
+                                        required_on=[require])
+        with self.assertRaises(unittest.SkipTest):
+            support.import_module(self.nonexistent_name,
+                                    required_on=['no real platform'])
+
+    def test_optional(self):
+        for optional in (sys.platform, os.name):
+            with self.assertRaises(unittest.SkipTest):
+                support.import_module(self.nonexistent_name,
+                                        optional=[optional])
+        with self.assertRaises(ImportError):
+            support.import_module(self.nonexistent_name,
+                                    optional=['no real platform'])
+
+
+def test_main():
+    support.run_unittest(
+            import_module_Tests
+        )
+
+
+if __name__ == '__main__':
+    test_main()
diff --git a/Lib/test/test_syslog.py b/Lib/test/test_syslog.py
--- a/Lib/test/test_syslog.py
+++ b/Lib/test/test_syslog.py
@@ -1,6 +1,7 @@
 
 from test import support
-syslog = support.import_module("syslog") #skip if not supported
+syslog = support.import_module("syslog", optional=['win32'])
+
 import unittest
 
 # XXX(nnorwitz): This test sucks.  I don't know of a platform independent way
diff --git a/Lib/test/test_winreg.py b/Lib/test/test_winreg.py
--- a/Lib/test/test_winreg.py
+++ b/Lib/test/test_winreg.py
@@ -8,7 +8,7 @@
 from platform import machine
 
 # Do this first so test will be skipped if module doesn't exist
-support.import_module('winreg')
+support.import_module('winreg', required_on=['win32'])
 # Now import everything
 from winreg import *
 
diff --git a/Lib/test/test_winsound.py b/Lib/test/test_winsound.py
--- a/Lib/test/test_winsound.py
+++ b/Lib/test/test_winsound.py
@@ -7,7 +7,7 @@
 import os
 import subprocess
 
-winsound = support.import_module('winsound')
+winsound = support.import_module('winsound', required_on=['win32'])
 ctypes = support.import_module('ctypes')
 import winreg