diff --git a/src/pretix/base/services/invoices.py b/src/pretix/base/services/invoices.py
index de4416e727..f153654c3b 100644
--- a/src/pretix/base/services/invoices.py
+++ b/src/pretix/base/services/invoices.py
@@ -191,6 +191,10 @@ def generate_invoice(order: Order):
     )
     invoice = build_invoice(invoice)
     invoice_pdf(invoice.pk)
+
+    if order.status in (Order.STATUS_CANCELED, Order.STATUS_REFUNDED):
+        generate_cancellation(invoice)
+
     return invoice
 
 
diff --git a/src/pretix/control/templates/pretixcontrol/order/index.html b/src/pretix/control/templates/pretixcontrol/order/index.html
index 0ac8f1e8ea..66e9adb2e4 100644
--- a/src/pretix/control/templates/pretixcontrol/order/index.html
+++ b/src/pretix/control/templates/pretixcontrol/order/index.html
@@ -131,7 +131,11 @@
                                                     action="{% url "control:event.order.reissueinvoice" event=request.event.slug organizer=request.event.organizer.slug code=order.code id=i.pk %}">
                                                 {% csrf_token %}
                                                 <button class="btn btn-default btn-xs">
-                                                    {% trans "Cancel and reissue" %}
+                                                    {% if order.status == "r" or order.status == "c" %}
+                                                        {% trans "Generate cancellation" %}
+                                                    {% else %}
+                                                        {% trans "Cancel and reissue" %}
+                                                    {% endif %}
                                                 </button>
                                             </form>
                                         {% endif %}
diff --git a/src/pretix/control/views/orders.py b/src/pretix/control/views/orders.py
index ed5dee2a2e..2281b927b0 100644
--- a/src/pretix/control/views/orders.py
+++ b/src/pretix/control/views/orders.py
@@ -366,8 +366,11 @@ class OrderInvoiceReissue(OrderView):
             if inv.canceled:
                 messages.error(self.request, _('The invoice has already been canceled.'))
             else:
-                generate_cancellation(inv)
-                inv = generate_invoice(self.order)
+                c = generate_cancellation(inv)
+                if self.order.status not in (Order.STATUS_CANCELED, Order.STATUS_REFUNDED):
+                    inv = generate_invoice(self.order)
+                else:
+                    inv = c
                 self.order.log_action('pretix.event.order.invoice.reissued', user=self.request.user, data={
                     'invoice': inv.pk
                 })