diff --git a/src/pretix/base/migrations/0194_membership_canceled.py b/src/pretix/base/migrations/0194_membership_canceled.py
new file mode 100644
index 0000000000..ee930940ed
--- /dev/null
+++ b/src/pretix/base/migrations/0194_membership_canceled.py
@@ -0,0 +1,18 @@
+# Generated by Django 3.2.3 on 2021-06-17 10:28
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('pretixbase', '0193_auto_20210611_1355'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='membership',
+            name='canceled',
+            field=models.BooleanField(default=False),
+        ),
+    ]
diff --git a/src/pretix/base/models/memberships.py b/src/pretix/base/models/memberships.py
index c47296eff5..e851f3fee5 100644
--- a/src/pretix/base/models/memberships.py
+++ b/src/pretix/base/models/memberships.py
@@ -118,6 +118,10 @@ class Membership(models.Model):
         verbose_name=_('Test mode'),
         default=False
     )
+    canceled = models.BooleanField(
+        verbose_name=_('Canceled'),
+        default=False
+    )
     customer = models.ForeignKey(
         Customer,
         related_name='memberships',
diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index cc8c34c720..a46f7844cc 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -599,6 +599,8 @@ class Order(LockModel, LoggedModel):
             for gc in op.issued_gift_cards.all():
                 if gc.value != op.price:
                     return False
+            if op.granted_memberships.with_usages().filter(usages__gt=0):
+                return False
         if self.user_cancel_deadline and now() > self.user_cancel_deadline:
             return False
         if self.status == Order.STATUS_PENDING:
diff --git a/src/pretix/base/services/memberships.py b/src/pretix/base/services/memberships.py
index 49d2a4e0bd..7ac480eeda 100644
--- a/src/pretix/base/services/memberships.py
+++ b/src/pretix/base/services/memberships.py
@@ -141,6 +141,11 @@ def validate_memberships_in_order(customer: Customer, positions: List[AbstractPo
                 _('You selected a membership that is connected to a different customer account.')
             )
 
+        if m.canceled:
+            raise ValidationError(
+                _('You selected membership that has been canceled.')
+            )
+
         if m.testmode != testmode:
             raise ValidationError(
                 _('You can only use a test mode membership for test mode tickets.')
diff --git a/src/pretix/base/services/orders.py b/src/pretix/base/services/orders.py
index 2ff5bcaafd..5e5e462f4e 100644
--- a/src/pretix/base/services/orders.py
+++ b/src/pretix/base/services/orders.py
@@ -177,6 +177,10 @@ def reactivate_order(order: Order, force: bool=False, user: User=None, auth=None
                         gc = GiftCard.objects.select_for_update().get(pk=gc.pk)
                         gc.transactions.create(value=position.price, order=order)
                         break
+
+                    for m in position.granted_memberships.all():
+                        m.canceled = False
+                        m.save()
         else:
             raise OrderError(is_available)
 
@@ -410,6 +414,10 @@ def _cancel_order(order, user=None, send_mail: bool=True, api_token=None, device
                 else:
                     gc.transactions.create(value=-position.price, order=order)
 
+            for m in position.granted_memberships.all():
+                m.canceled = True
+                m.save()
+
         if cancellation_fee:
             with order.event.lock():
                 for position in order.positions.all():
@@ -1768,7 +1776,26 @@ class OrderChangeManager:
                     else:
                         gc.transactions.create(value=-op.position.price, order=self.order)
 
+                for m in op.position.granted_memberships.with_usages().all():
+                    m.canceled = True
+                    m.save()
+
                 for opa in op.position.addons.all():
+                    for gc in opa.issued_gift_cards.all():
+                        gc = GiftCard.objects.select_for_update().get(pk=gc.pk)
+                        if gc.value < opa.position.price:
+                            raise OrderError(_(
+                                'A position can not be canceled since the gift card {card} purchased in this order has '
+                                'already been redeemed.').format(
+                                card=gc.secret
+                            ))
+                        else:
+                            gc.transactions.create(value=-opa.position.price, order=self.order)
+
+                    for m in opa.granted_memberships.with_usages().all():
+                        m.canceled = True
+                        m.save()
+
                     self.order.log_action('pretix.event.order.changed.cancel', user=self.user, auth=self.auth, data={
                         'position': opa.pk,
                         'positionid': opa.positionid,
diff --git a/src/pretix/control/forms/organizer.py b/src/pretix/control/forms/organizer.py
index 5363f053be..6317aa12e6 100644
--- a/src/pretix/control/forms/organizer.py
+++ b/src/pretix/control/forms/organizer.py
@@ -560,7 +560,7 @@ class MembershipUpdateForm(forms.ModelForm):
 
     class Meta:
         model = Membership
-        fields = ['testmode', 'membership_type', 'date_start', 'date_end', 'attendee_name_parts']
+        fields = ['testmode', 'membership_type', 'date_start', 'date_end', 'attendee_name_parts', 'canceled']
         field_classes = {
             'date_start': SplitDateTimeField,
             'date_end': SplitDateTimeField,
diff --git a/src/pretix/control/templates/pretixcontrol/organizers/customer.html b/src/pretix/control/templates/pretixcontrol/organizers/customer.html
index 3767e81576..51a39d75d3 100644
--- a/src/pretix/control/templates/pretixcontrol/organizers/customer.html
+++ b/src/pretix/control/templates/pretixcontrol/organizers/customer.html
@@ -81,7 +81,9 @@
                     {% for m in memberships %}
                         <tr>
                             <td>
+                                {% if m.canceled %}<del>{% endif %}
                                 {{ m.membership_type.name }}
+                                {% if m.canceled %}</del>{% endif %}
                                 {% if m.testmode %}<span class="label label-warning">{% trans "TEST MODE" %}</span>{% endif %}
                             </td>
                             <td>
diff --git a/src/pretix/control/views/organizer.py b/src/pretix/control/views/organizer.py
index 6c65ba95d0..9eb76cc68f 100644
--- a/src/pretix/control/views/organizer.py
+++ b/src/pretix/control/views/organizer.py
@@ -1891,7 +1891,6 @@ class MembershipDeleteView(OrganizerDetailViewMixin, OrganizerPermissionRequired
     template_name = 'pretixcontrol/organizers/customer_membership_delete.html'
     permission = 'can_manage_customers'
     context_object_name = 'membership'
-    form_class = MembershipUpdateForm
 
     def get_object(self, queryset=None):
         return get_object_or_404(
diff --git a/src/pretix/presale/checkoutflow.py b/src/pretix/presale/checkoutflow.py
index 7595c9b332..5b8ab0bdd4 100644
--- a/src/pretix/presale/checkoutflow.py
+++ b/src/pretix/presale/checkoutflow.py
@@ -376,6 +376,7 @@ class MembershipStep(QuestionsViewMixin, CartMixin, TemplateFlowStep):
 
         memberships = list(self.cart_customer.memberships.with_usages().filter(
             Q(Q(membership_type__max_usages__isnull=True) | Q(usages__lt=F('membership_type__max_usages'))),
+            canceled=False
         ).select_related('membership_type'))
 
         for p in self.applicable_positions:
diff --git a/src/pretix/presale/templates/pretixpresale/organizers/customer_profile.html b/src/pretix/presale/templates/pretixpresale/organizers/customer_profile.html
index 6dd8f02d57..452cd1b5ce 100644
--- a/src/pretix/presale/templates/pretixpresale/organizers/customer_profile.html
+++ b/src/pretix/presale/templates/pretixpresale/organizers/customer_profile.html
@@ -58,7 +58,9 @@
             {% for m in memberships %}
                 <tr>
                     <td>
+                        {% if m.canceled %}<del>{% endif %}
                         {{ m.membership_type.name }}
+                        {% if m.canceled %}</del>{% endif %}
                         {% if m.testmode %}<span class="label label-warning">{% trans "TEST MODE" %}</span>{% endif %}
                     </td>
                     <td>
diff --git a/src/tests/base/test_memberships.py b/src/tests/base/test_memberships.py
index 5bbf20a61e..ee61e373db 100644
--- a/src/tests/base/test_memberships.py
+++ b/src/tests/base/test_memberships.py
@@ -227,6 +227,27 @@ def test_validate_membership_ensure_locking(event, customer, membership, requiri
         assert any('FOR UPDATE' in s['sql'] for s in captured)
 
 
+@pytest.mark.django_db
+def test_validate_membership_canceled(event, customer, membership, requiring_ticket, membership_type):
+    with pytest.raises(ValidationError) as excinfo:
+        membership.canceled = True
+        membership.save()
+        validate_memberships_in_order(
+            customer,
+            [
+                CartPosition(
+                    item=requiring_ticket,
+                    used_membership=membership
+                )
+            ],
+            event,
+            lock=False,
+            ignored_order=None,
+            testmode=False,
+        )
+    assert "canceled" in str(excinfo.value)
+
+
 @pytest.mark.django_db
 def test_validate_membership_test_mode(event, customer, membership, requiring_ticket, membership_type):
     with pytest.raises(ValidationError) as excinfo:
diff --git a/src/tests/base/test_models.py b/src/tests/base/test_models.py
index df604d60a8..35c8a7a5e2 100644
--- a/src/tests/base/test_models.py
+++ b/src/tests/base/test_models.py
@@ -1233,6 +1233,27 @@ class OrderTestCase(BaseQuotaTestCase):
         )
         assert not self.order.user_cancel_allowed
 
+    @classscope(attr='o')
+    def test_can_cancel_order_with_membership(self):
+        mt = self.event.organizer.membership_types.create(name="foo")
+        customer = self.event.organizer.customers.create()
+        self.order.customer = customer
+        self.order.save()
+        item1 = Item.objects.create(event=self.event, name="Ticket", default_price=23,
+                                    admission=True, allow_cancel=True, issue_giftcard=True)
+        p = OrderPosition.objects.create(order=self.order, item=item1,
+                                         variation=None, price=23)
+        m = customer.memberships.create(
+            membership_type=mt,
+            date_start=now(),
+            date_end=now(),
+            granted_in=p,
+        )
+        # yeah, doesn't really make sense on same order, but good enough for the test
+        OrderPosition.objects.create(order=self.order, item=item1,
+                                     variation=None, price=23, used_membership=m)
+        assert not self.order.user_cancel_allowed
+
     @classscope(attr='o')
     def test_can_cancel_order_free(self):
         self.order.status = Order.STATUS_PAID
diff --git a/src/tests/base/test_orders.py b/src/tests/base/test_orders.py
index ce93a369d3..3b077584ee 100644
--- a/src/tests/base/test_orders.py
+++ b/src/tests/base/test_orders.py
@@ -1166,6 +1166,23 @@ class OrderChangeManagerTests(TestCase):
         self.ocm.commit()
         assert gc.value == Decimal('0.00')
 
+    @classscope(attr='o')
+    def test_cancel_issued_membership(self):
+        mt = self.event.organizer.membership_types.create(name="foo")
+        customer = self.event.organizer.customers.create()
+        self.order.customer = customer
+        self.o.save()
+        m = customer.memberships.create(
+            membership_type=mt,
+            date_start=now(),
+            date_end=now(),
+            granted_in=self.order.positions.first(),
+        )
+        self.ocm.cancel(self.op1)
+        self.ocm.commit()
+        m.refresh_from_db()
+        assert m.canceled
+
     @classscope(attr='o')
     def test_cancel_issued_giftcard_used(self):
         gc = self.o.issued_gift_cards.create(currency="EUR", issued_in=self.op1)
@@ -2419,6 +2436,21 @@ class OrderChangeManagerTests(TestCase):
         op.refresh_from_db()
         assert op.secret != s
 
+    @classscope(attr='o')
+    def test_cancel_order_membership(self):
+        mt = self.event.organizer.membership_types.create(name="foo")
+        customer = self.event.organizer.customers.create()
+        self.order.customer = customer
+        m = customer.memberships.create(
+            membership_type=mt,
+            date_start=now(),
+            date_end=now(),
+            granted_in=self.order.positions.first(),
+        )
+        cancel_order(self.order)
+        m.refresh_from_db()
+        assert m.canceled
+
     @classscope(attr='o')
     def test_auto_change_payment_fee(self):
         fee2 = self.order.fees.create(fee_type=OrderFee.FEE_TYPE_SHIPPING, value=Decimal('0.50'))
@@ -3019,3 +3051,20 @@ class OrderReactivateTest(TestCase):
         gc = self.o.issued_gift_cards.create(currency="EUR", issued_in=self.op1)
         reactivate_order(self.order)
         assert gc.value == 23
+
+    @classscope(attr='o')
+    def test_reactivate_membership(self):
+        mt = self.event.organizer.membership_types.create(name="foo")
+        customer = self.event.organizer.customers.create()
+        self.order.customer = customer
+        self.order.save()
+        m = customer.memberships.create(
+            membership_type=mt,
+            date_start=now(),
+            date_end=now(),
+            granted_in=self.order.positions.first(),
+            canceled=True,
+        )
+        reactivate_order(self.order)
+        m.refresh_from_db()
+        assert not m.canceled