diff --git a/src/pretix/control/templates/pretixcontrol/items/question.html b/src/pretix/control/templates/pretixcontrol/items/question.html
index 3f0d3e5d9..202ae590a 100644
--- a/src/pretix/control/templates/pretixcontrol/items/question.html
+++ b/src/pretix/control/templates/pretixcontrol/items/question.html
@@ -17,10 +17,27 @@
 			{% bootstrap_field form.type layout="horizontal" %}
 			{% bootstrap_field form.required layout="horizontal" %}
 		</fieldset>
+        <div class="alert alert-info alert-required-boolean">
+            {% blocktrans trimmed %}
+                If you mark a Yes/No question as required, it means that the user has to select Yes and No is not
+                accepted. If you want to allow both options, do not make this field required.
+            {% endblocktrans %}
+        </div>
 		<div class="form-group submit-group">
             <button type="submit" class="btn btn-primary btn-save">
                 {% trans "Save" %}
             </button>
 		</div>
 	</form>
+    <script type="text/javascript">
+    $(function() {
+        function alert_required_boolean() {
+            var show = $("#id_type").val() == "B" && $("#id_required").prop("checked");
+            $(".alert-required-boolean").toggle(show);
+        }
+        $("#id_type").change(alert_required_boolean);
+        $("#id_required").change(alert_required_boolean);
+        alert_required_boolean();
+    });
+    </script>
 {% endblock %}
diff --git a/src/tests/presale/test_checkout.py b/src/tests/presale/test_checkout.py
index 1ea4a8830..8b564b24f 100644
--- a/src/tests/presale/test_checkout.py
+++ b/src/tests/presale/test_checkout.py
@@ -100,34 +100,6 @@ class CheckoutTestCase(TestCase):
         self.assertEqual(cr1.answers.filter(question=q2).count(), 1)
         self.assertFalse(cr2.answers.filter(question=q2).exists())
 
-    @expectedFailure
-    def test_boolean_required_question(self):
-        """
-        Expected to fail. See https://github.com/pretix/pretix/issues/19
-        """
-        q1 = Question.objects.create(
-            event=self.event, question='Breakfast', type=Question.TYPE_BOOLEAN,
-            required=True
-        )
-        self.ticket.questions.add(q1)
-        cr1 = CartPosition.objects.create(
-            event=self.event, user=self.user, item=self.ticket,
-            price=23, expires=now() + timedelta(minutes=10)
-        )
-        response = self.client.get('/%s/%s/checkout' % (self.orga.slug, self.event.slug), follow=True)
-        doc = BeautifulSoup(response.rendered_content)
-        self.assertEqual(len(doc.select('input[name=%s-question_%s]' % (cr1.identity, q1.identity))), 1)
-
-        response = self.client.post('/%s/%s/checkout' % (self.orga.slug, self.event.slug), {
-            '%s-question_%s' % (cr1.identity, q1.identity): '',
-        }, follow=True)
-        self.assertRedirects(response, '/%s/%s/checkout/payment' % (self.orga.slug, self.event.slug),
-                             target_status_code=200)
-
-        cr1 = CartPosition.objects.current.get(identity=cr1.identity)
-        self.assertEqual(cr1.answers.filter(question=q1).count(), 1)
-        self.assertEqual(cr1.answers.get(question=q1).value, 'False')
-
     def test_attendee_name_required(self):
         self.event.settings.set('attendee_names_asked', True)
         self.event.settings.set('attendee_names_required', True)