diff --git a/src/pretix/presale/templates/pretixpresale/event/order.html b/src/pretix/presale/templates/pretixpresale/event/order.html
index da576a3c47..eef533ae83 100644
--- a/src/pretix/presale/templates/pretixpresale/event/order.html
+++ b/src/pretix/presale/templates/pretixpresale/event/order.html
@@ -182,13 +182,19 @@
                         </h3>
                     </div>
                     <div class="panel-body">
-                        <form class="form-inline helper-display-inline" method="post"
-                                action="{% eventurl event "presale:event.order.geninvoice" order=order.code secret=order.secret %}">
-                            {% csrf_token %}
-                            <button class="btn btn-default">
-                                {% trans "Request invoice" %}
-                            </button>
-                        </form>
+                        {% if generate_invoice_requires == "payment" %}
+                            <div class="alert alert-info">
+                                {% trans "You need to select a payment method above before you can request an invoice." %}
+                            </div>
+                        {% else %}
+                            <form class="form-inline helper-display-inline" method="post"
+                                    action="{% eventurl event "presale:event.order.geninvoice" order=order.code secret=order.secret %}">
+                                {% csrf_token %}
+                                <button class="btn btn-default">
+                                    {% trans "Request invoice" %}
+                                </button>
+                            </form>
+                        {% endif %}
                     </div>
                 </div>
             </div>
diff --git a/src/pretix/presale/views/order.py b/src/pretix/presale/views/order.py
index f0719acc33..8ff78dbeae 100644
--- a/src/pretix/presale/views/order.py
+++ b/src/pretix/presale/views/order.py
@@ -187,6 +187,11 @@ class OrderDetails(EventViewMixin, OrderDetailMixin, CartMixin, TicketPageMixin,
             )
         )
         ctx['can_generate_invoice'] = invoice_qualified(self.order) and can_generate_invoice
+        if ctx['can_generate_invoice']:
+            if not self.order.payments.exclude(
+                    state__in=[OrderPayment.PAYMENT_STATE_CANCELED, OrderPayment.PAYMENT_STATE_FAILED]
+            ).exists() and self.order.status == Order.STATUS_PENDING:
+                ctx['generate_invoice_requires'] = 'payment'
         ctx['url'] = build_absolute_uri(
             self.request.event, 'presale:event.order', kwargs={
                 'order': self.order.code,
@@ -603,6 +608,10 @@ class OrderInvoiceCreate(EventViewMixin, OrderDetailMixin, View):
                     self.request.event.settings.get('invoice_generate') == 'paid'
                     and self.order.status == Order.STATUS_PAID
                 )
+            ) and not (
+                not self.order.payments.exclude(
+                    state__in=[OrderPayment.PAYMENT_STATE_CANCELED, OrderPayment.PAYMENT_STATE_FAILED]
+                ).exists() and self.order.status == Order.STATUS_PENDING
             )
         )
         if not can_generate_invoice or not invoice_qualified(self.order):
diff --git a/src/tests/presale/test_orders.py b/src/tests/presale/test_orders.py
index 1ca0be0cc1..8eac5382d8 100644
--- a/src/tests/presale/test_orders.py
+++ b/src/tests/presale/test_orders.py
@@ -446,8 +446,20 @@ class OrdersTest(BaseOrdersTest):
             {})
         assert 404 == response.status_code
 
+    def test_invoice_create_require_payment(self):
+        self.event.settings.set('invoice_generate', 'user')
+        response = self.client.post(
+            '/%s/%s/order/%s/%s/invoice' % (self.orga.slug, self.event.slug, self.order.code, self.order.secret),
+            {}, follow=True)
+        assert 'alert-danger' in response.rendered_content
+        with scopes_disabled():
+            assert not self.order.invoices.exists()
+
     def test_invoice_create_ok(self):
         self.event.settings.set('invoice_generate', 'user')
+        with scopes_disabled():
+            self.order.payments.create(provider='banktransfer', state=OrderPayment.PAYMENT_STATE_CONFIRMED,
+                                       amount=self.order.total)
         response = self.client.post(
             '/%s/%s/order/%s/%s/invoice' % (self.orga.slug, self.event.slug, self.order.code, self.order.secret),
             {}, follow=True)