diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index af1d51e435..d01853d13d 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -907,6 +907,11 @@ class Order(LockModel, LoggedModel):
             return self.expires
 
         expires = self.expires.date() + timedelta(days=delay)
+        if self.event.settings.get('payment_term_weekdays'):
+            if expires.weekday() == 5:
+                expires += timedelta(days=2)
+            elif expires.weekday() == 6:
+                expires += timedelta(days=1)
 
         tz = ZoneInfo(self.event.settings.timezone)
         expires = make_aware(datetime.combine(
diff --git a/src/pretix/base/settings.py b/src/pretix/base/settings.py
index bd8d2f28b5..0fa4af05c6 100644
--- a/src/pretix/base/settings.py
+++ b/src/pretix/base/settings.py
@@ -941,9 +941,9 @@ DEFAULTS = {
         'form_kwargs': dict(
             label=_('Expiration delay'),
             help_text=_("The order will only actually expire this many days after the expiration date communicated "
-                        "to the customer. However, this will not delay beyond the \"last date of payments\" "
-                        "configured above, which is always enforced. The delay may also end on a weekend regardless "
-                        "of the other settings above."),
+                        "to the customer. If you select \"Only end payment terms on weekdays\" above, this will also "
+                        "be respected. However, this will not delay beyond the \"last date of payments\" "
+                        "configured above, which is always enforced."),
             # Every order in between the official expiry date and the delayed expiry date has a performance penalty
             # for the cron job, so we limit this feature to 30 days to prevent arbitrary numbers of orders needing
             # to be checked.
diff --git a/src/pretix/control/views/event.py b/src/pretix/control/views/event.py
index fcf19c6450..35bf3c8116 100644
--- a/src/pretix/control/views/event.py
+++ b/src/pretix/control/views/event.py
@@ -783,8 +783,8 @@ class MailSettingsRendererPreview(MailSettingsPreview):
         return ctx
 
     def get(self, request, *args, **kwargs):
-        v = str(request.event.settings.mail_text_order_placed)
-        v = format_map(v, self.placeholders('mail_text_order_placed'))
+        v = str(request.event.settings.mail_text_order_payment_failed)
+        v = format_map(v, self.placeholders('mail_text_order_payment_failed'))
         renderers = request.event.get_html_mail_renderers()
         if request.GET.get('renderer') in renderers:
             with rolledback_transaction():
diff --git a/src/tests/base/test_orders.py b/src/tests/base/test_orders.py
index 8745697a27..7edc74ab6f 100644
--- a/src/tests/base/test_orders.py
+++ b/src/tests/base/test_orders.py
@@ -412,6 +412,7 @@ def test_expiring_auto_disabled(event):
 def test_expiring_auto_delayed(event):
     event.settings.set('payment_term_expire_delay_days', 3)
     event.settings.set('payment_term_last', date(2023, 7, 2))
+    event.settings.set('payment_term_weekdays', False)
     event.settings.set('timezone', 'Europe/Berlin')
     o1 = Order.objects.create(
         code='FOO', event=event, email='dummy@dummy.test',
@@ -458,6 +459,21 @@ def test_expiring_auto_delayed(event):
         assert o2.status == Order.STATUS_EXPIRED
 
 
+@pytest.mark.django_db
+def test_expiring_auto_delayed_weekdays(event):
+    event.settings.set('payment_term_expire_delay_days', 2)
+    event.settings.set('payment_term_weekdays', True)
+    event.settings.set('timezone', 'Europe/Berlin')
+    o1 = Order.objects.create(
+        code='FOO', event=event, email='dummy@dummy.test',
+        status=Order.STATUS_PENDING,
+        datetime=datetime(2023, 6, 22, 12, 13, 14, tzinfo=zoneinfo.ZoneInfo("Europe/Berlin")),
+        expires=datetime(2023, 6, 30, 23, 59, 59, tzinfo=zoneinfo.ZoneInfo("Europe/Berlin")),
+        total=0,
+    )
+    assert o1.payment_term_expire_date == o1.expires + timedelta(days=3)
+
+
 @pytest.mark.django_db
 def test_do_not_expire_if_approval_pending(event):
     o1 = Order.objects.create(