diff --git a/tests/roots/test-ext-doctest-skipif/conf.py b/tests/roots/test-ext-doctest-skipif/conf.py
new file mode 100644
index 000000000..5f3e89786
--- /dev/null
+++ b/tests/roots/test-ext-doctest-skipif/conf.py
@@ -0,0 +1,10 @@
+extensions = ['sphinx.ext.doctest']
+
+project = 'test project for the doctest :skipif: directive'
+master_doc = 'skipif'
+source_suffix = '.txt'
+exclude_patterns = ['_build']
+
+doctest_global_setup = '''
+from test_ext_doctest import record
+'''
\ No newline at end of file
diff --git a/tests/roots/test-ext-doctest-skipif/skipif.txt b/tests/roots/test-ext-doctest-skipif/skipif.txt
new file mode 100644
index 000000000..c5bd39821
--- /dev/null
+++ b/tests/roots/test-ext-doctest-skipif/skipif.txt
@@ -0,0 +1,81 @@
+Testing the doctest extension's `:skipif:` option
+=================================================
+
+testsetup
+---------
+
+.. testsetup:: group-skipif
+   :skipif: record('testsetup', ':skipif:', True) != 'this will be True'
+
+   record('testsetup', 'body', True)
+
+.. testsetup:: group-skipif
+   :skipif: record('testsetup', ':skipif:', False) == 'this will be False'
+
+   record('testsetup', 'body', False)
+
+
+doctest
+-------
+.. doctest:: group-skipif
+   :skipif: record('doctest', ':skipif:', True) != 'this will be True'
+
+   >>> print(record('doctest', 'body', True))
+   The test is skipped, and this expected text is ignored
+
+
+.. doctest::
+   :skipif: record('doctest', ':skipif:', False) == 'this will be False'
+
+   >>> print(record('doctest', 'body', False))
+   Recorded doctest body False
+
+
+testcode and testoutput
+-----------------------
+
+testcode skipped
+~~~~~~~~~~~~~~~~
+
+.. testcode:: group-skipif
+   :skipif: record('testcode', ':skipif:', True) != 'this will be True'
+
+   print(record('testcode', 'body', True))
+
+.. testoutput:: group-skipif
+   :skipif: record('testoutput-1', ':skipif:', True) != 'this will be True'
+
+   The previous testcode is skipped, and the :skipif: condition is True,
+   so this testoutput is ignored
+
+testcode executed
+~~~~~~~~~~~~~~~~~
+
+.. testcode:: group-skipif
+   :skipif: record('testcode', ':skipif:', False) == 'this will be False'
+
+   print(record('testcode', 'body', False))
+
+.. testoutput:: group-skipif
+   :skipif: record('testoutput-2', ':skipif:', False) == 'this will be False'
+
+   Recorded testcode body False
+
+.. testoutput:: group-skipif
+   :skipif: record('testoutput-2', ':skipif:', True) != 'this will be True'
+
+   The :skipif: condition is False, so this testoutput is ignored
+
+
+testcleanup
+-----------
+
+.. testcleanup:: group-skipif
+   :skipif: record('testcleanup', ':skipif:', True) != 'this will be True'
+
+   record('testcleanup', 'body', True)
+
+.. testcleanup:: group-skipif
+   :skipif: record('testcleanup', ':skipif:', False) == 'this will be False'
+
+   record('testcleanup', 'body', False)
diff --git a/tests/test_ext_doctest.py b/tests/test_ext_doctest.py
index 7137af31b..5ae3c0f7a 100644
--- a/tests/test_ext_doctest.py
+++ b/tests/test_ext_doctest.py
@@ -61,6 +61,51 @@ def cleanup_call():
     cleanup_called += 1
 
 
+recorded_calls = set()
+
+
+@pytest.mark.sphinx('doctest', testroot='ext-doctest-skipif')
+def test_skipif(app, status, warning):
+    """Tests for the :skipif: option
+
+    The tests are separated into a different test root directory since the
+    ``app`` object only evaluates options once in its lifetime. If these tests
+    were combined with the other doctest tests, the ``:skipif:`` evaluations
+    would be recorded only on the first ``app.builder.build_all()`` run, i.e.
+    in ``test_build`` above, and the assertion below would fail.
+
+    """
+    global recorded_calls
+    recorded_calls = set()
+    app.builder.build_all()
+    if app.statuscode != 0:
+        assert False, 'failures in doctests:' + status.getvalue()
+    # The `:skipif:` expressions are always run.
+    # Actual tests and setup/cleanup code is only run if the `:skipif:`
+    # expression evaluates to a False value.
+    assert recorded_calls == {('testsetup', ':skipif:', True),
+                              ('testsetup', ':skipif:', False),
+                              ('testsetup', 'body', False),
+                              ('doctest', ':skipif:', True),
+                              ('doctest', ':skipif:', False),
+                              ('doctest', 'body', False),
+                              ('testcode', ':skipif:', True),
+                              ('testcode', ':skipif:', False),
+                              ('testcode', 'body', False),
+                              ('testoutput-1', ':skipif:', True),
+                              ('testoutput-2', ':skipif:', True),
+                              ('testoutput-2', ':skipif:', False),
+                              ('testcleanup', ':skipif:', True),
+                              ('testcleanup', ':skipif:', False),
+                              ('testcleanup', 'body', False)}
+
+
+def record(directive, part, should_skip):
+    global recorded_calls
+    recorded_calls.add((directive, part, should_skip))
+    return 'Recorded {} {} {}'.format(directive, part, should_skip)
+
+
 @pytest.mark.xfail(
     PY2, reason='node.source points to document instead of filename',
 )