diff --git a/src/pretix/api/serializers/order.py b/src/pretix/api/serializers/order.py
index 418dbc00f9..639cac78c8 100644
--- a/src/pretix/api/serializers/order.py
+++ b/src/pretix/api/serializers/order.py
@@ -1585,6 +1585,11 @@ class OrderCreateSerializer(I18nAwareModelSerializer):
                 order.invoice_address = ia
                 ia.last_modified = now()
 
+        if order.customer_id:
+            memberships = order.customer.memberships.filter(testmode=order.testmode).select_related('membership_type')
+        else:
+            memberships = []
+
         # Generate position objects
         pos_map = {}
         for pos_data in positions_data:
@@ -1655,7 +1660,12 @@ class OrderCreateSerializer(I18nAwareModelSerializer):
                 order.sales_channel,
                 [
                     (cp.item_id, cp.subevent_id, cp.subevent.date_from if cp.subevent_id else None, cp.price,
-                     cp.addon_to, cp.is_bundled, pos._voucher_discount)
+                     cp.addon_to, cp.is_bundled, pos._voucher_discount, [
+                         m for m in memberships if m.is_valid(
+                             cp.subevent or self.context['event'],
+                             cp.valid_from,
+                         )
+                     ])
                     for cp in order_positions
                 ]
             )
diff --git a/src/pretix/base/migrations/0311_discount_require_membership_and_more.py b/src/pretix/base/migrations/0311_discount_require_membership_and_more.py
new file mode 100644
index 0000000000..441a2534e1
--- /dev/null
+++ b/src/pretix/base/migrations/0311_discount_require_membership_and_more.py
@@ -0,0 +1,24 @@
+# Generated by Django 5.2.17 on 2026-09-13 18:32
+
+import django.db.models.deletion
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("pretixbase", "0310_question_valid_string_length_min"),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name="discount",
+            name="require_membership",
+            field=models.BooleanField(default=False),
+        ),
+        migrations.AddField(
+            model_name="discount",
+            name="require_membership_types",
+            field=models.ManyToManyField(to="pretixbase.membershiptype"),
+        ),
+    ]
diff --git a/src/pretix/base/models/customers.py b/src/pretix/base/models/customers.py
index e53e771278..004a9b7a29 100644
--- a/src/pretix/base/models/customers.py
+++ b/src/pretix/base/models/customers.py
@@ -296,7 +296,7 @@ class Customer(LoggedModel):
         return self.memberships.active(for_event).with_usages().filter(
             Q(membership_type__max_usages__isnull=True) | Q(usages__lt=F('membership_type__max_usages')),
             testmode=testmode,
-        )
+        ).select_related('membership_type')
 
     def send_activation_mail(self):
         from pretix.base.services.mail import mail
diff --git a/src/pretix/base/models/discount.py b/src/pretix/base/models/discount.py
index 65d10b62e9..d36878fc1b 100644
--- a/src/pretix/base/models/discount.py
+++ b/src/pretix/base/models/discount.py
@@ -19,12 +19,12 @@
 # You should have received a copy of the GNU Affero General Public License along with this program.  If not, see
 # <https://www.gnu.org/licenses/>.
 #
-
-from collections import defaultdict, namedtuple
+import datetime
+from collections import defaultdict
 from decimal import Decimal
 from itertools import groupby
 from math import ceil, inf
-from typing import Dict
+from typing import TYPE_CHECKING, Dict, List, NamedTuple, Optional
 
 from django.core.exceptions import ValidationError
 from django.core.validators import MinValueValidator
@@ -35,10 +35,20 @@ from django_scopes import ScopedManager
 
 from pretix.base.decimal import round_decimal
 from pretix.base.models.base import LoggedModel
+from pretix.base.timemachine import time_machine_now
 
-PositionInfo = namedtuple('PositionInfo',
-                          ['item_id', 'subevent_id', 'subevent_date_from', 'line_price_gross', 'addon_to',
-                           'voucher_discount'])
+if TYPE_CHECKING:
+    from pretix.base.models import Membership
+
+
+class PositionInfo(NamedTuple):
+    item_id: int
+    subevent_id: Optional[int]
+    subevent_date_from: Optional[datetime.datetime]
+    line_price_gross: Decimal
+    addon_to: bool
+    voucher_discount: Decimal
+    memberships_valid_by_time: Optional[List["Membership"]] = None
 
 
 class Discount(LoggedModel):
@@ -249,6 +259,46 @@ class Discount(LoggedModel):
                 ]}
             )
 
+        if data.get('require_membership'):
+            if not data.get('require_membership_types'):
+                raise ValidationError(
+                    {'require_membership_types': [
+                        _("If a valid membership is required, at least one valid membership type needs to be selected.")
+                    ]}
+                )
+            for mt in data.get('require_membership_types', []):
+                # These conditions are a bit annoying/surprising, we could also just "ignore" the
+                # transferable/allow_parallel_usage/max_usages flags, but maybe we DO want to honor them for discounts
+                # some day for use cases like "every member can get one discounted ticket per show for themselves", and
+                # then we'd be unable to move forward if we historically ignored them.
+                if not mt.transferable:
+                    raise ValidationError(
+                        {'require_membership_types': [
+                            _('The membership type "{type}" cannot be used for discounts since it is not transferable, '
+                              'which is currently not supported for discounts.').format(
+                                type=mt.name,
+                            )
+                        ]}
+                    )
+                elif not mt.allow_parallel_usage:
+                    raise ValidationError(
+                        {'require_membership_types': [
+                            _('The membership type "{type}" cannot be used for discounts since it does not allow parallel '
+                              'usage, which is currently not supported for discounts.').format(
+                                type=mt.name,
+                            )
+                        ]}
+                    )
+                elif mt.max_usages is not None:
+                    raise ValidationError(
+                        {'require_membership_types': [
+                            _('The membership type "{type}" cannot be used for discounts since it has a maximum number of '
+                              'usages, which is currently not supported for discounts.').format(
+                                type=mt.name,
+                            )
+                        ]}
+                    )
+
     def allow_delete(self):
         return not self.orderposition_set.exists()
 
@@ -260,6 +310,7 @@ class Discount(LoggedModel):
             'benefit_only_apply_to_cheapest_n_matches': self.benefit_only_apply_to_cheapest_n_matches,
             'subevent_mode': self.subevent_mode,
             'benefit_same_products': self.benefit_same_products,
+            # many-to-many is not passed here, therefore we also call validate_config in form and serializer
         })
 
     def is_available_by_time(self, now_dt=None) -> bool:
@@ -410,19 +461,25 @@ class Discount(LoggedModel):
         limit_products = set()
         if not self.condition_all_products:
             limit_products = {p.pk for p in self.condition_limit_products.all()}
+        membership_types = set()
+        if self.require_membership and self.require_membership_types:
+            membership_types = {mt.pk for mt in self.require_membership_types.all()}
 
         # First, filter out everything not even covered by our product scope
         condition_candidates = [
             idx
-            for idx, (item_id, subevent_id, subevent_date_from, line_price_gross, is_addon_to, voucher_discount) in
+            for idx, p in
             positions.items()
             if (
-                (self.condition_all_products or item_id in limit_products) and
-                (self.condition_apply_to_addons or not is_addon_to) and
-                (not self.condition_ignore_voucher_discounted or voucher_discount is None or voucher_discount == Decimal('0.00'))
-                and (not subevent_id or (
-                    self.subevent_date_from is None or subevent_date_from >= self.subevent_date_from)) and (
-                        self.subevent_date_until is None or subevent_date_from <= self.subevent_date_until)
+                (self.condition_all_products or p.item_id in limit_products) and
+                (self.condition_apply_to_addons or not p.addon_to) and
+                (not self.condition_ignore_voucher_discounted or p.voucher_discount is None or p.voucher_discount == Decimal('0.00')) and
+                (not p.subevent_id or (
+                    self.subevent_date_from is None or p.subevent_date_from >= self.subevent_date_from)) and (
+                        self.subevent_date_until is None or p.subevent_date_from <= self.subevent_date_until) and
+                (not self.require_membership or (
+                    p.memberships_valid_by_time and any(m.membership_type_id in membership_types for m in p.memberships_valid_by_time)
+                ))
             )
         ]
 
@@ -432,12 +489,15 @@ class Discount(LoggedModel):
             benefit_products = {p.pk for p in self.benefit_limit_products.all()}
             benefit_candidates = [
                 idx
-                for idx, (item_id, subevent_id, subevent_date_from, line_price_gross, is_addon_to, voucher_discount) in
+                for idx, p in
                 positions.items()
                 if (
-                    item_id in benefit_products and
-                    (self.benefit_apply_to_addons or not is_addon_to) and
-                    (not self.benefit_ignore_voucher_discounted or voucher_discount is None or voucher_discount == Decimal('0.00'))
+                    p.item_id in benefit_products and
+                    (self.benefit_apply_to_addons or not p.addon_to) and
+                    (not self.benefit_ignore_voucher_discounted or p.voucher_discount is None or p.voucher_discount == Decimal('0.00')) and
+                    (not self.require_membership or (
+                        p.memberships_valid_by_time and any(m.membership_type_id in membership_types for m in p.memberships_valid_by_time)
+                    ))
                 )
             ]
 
@@ -538,3 +598,38 @@ class Discount(LoggedModel):
                     None
                 )
         return result
+
+    def condition_matches_product(self, item) -> bool:
+        return self.condition_all_products or item in self.condition_limit_products.all()
+
+    def valid_for_memberships(self, memberships, event, subevent, item, requested_valid_from=None) -> bool:
+        if not self.require_membership_types:
+            return True
+        if not memberships:
+            return False
+        memberships = [
+            m for m in memberships
+            # Filter currently unsupported configurations
+            if (
+                m.membership_type.max_usages is None and
+                m.membership_type.transferable and
+                m.membership_type.allow_parallel_usage and
+                # Filter list of membership types
+                m.membership_type in self.require_membership_types.all()
+            )
+        ]
+        valid_from, _ = item.compute_validity(
+            requested_start=(
+                max(requested_valid_from, time_machine_now())
+                if requested_valid_from and item.validity_dynamic_start_choice
+                else time_machine_now()
+            ),
+            override_tz=self.event.timezone,
+        )
+        return any(
+            m.is_valid(
+                subevent or event,
+                valid_from,
+                valid_from_not_chosen=item.validity_dynamic_start_choice and not requested_valid_from
+            ) for m in memberships
+        )
diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index 15dba58a98..13a5d91ba6 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -3413,6 +3413,15 @@ class CartPosition(AbstractPosition):
     def valid_until(self):
         return self.predicted_validity[1]
 
+    def memberships_valid_by_time(self, memberships):
+        return [
+            m for m in memberships if m.is_valid(
+                self.subevent or self.event,
+                self.valid_from,
+                valid_from_not_chosen=self.item.validity_dynamic_start_choice and not self.requested_valid_from
+            ) for m in memberships
+        ]
+
 
 class InvoiceAddress(models.Model):
     last_modified = models.DateTimeField(auto_now=True)
diff --git a/src/pretix/base/services/cart.py b/src/pretix/base/services/cart.py
index 9e1c2e45fc..9fdd361b8b 100644
--- a/src/pretix/base/services/cart.py
+++ b/src/pretix/base/services/cart.py
@@ -47,6 +47,7 @@ from django.db import DatabaseError, transaction
 from django.db.models import Count, Exists, IntegerField, OuterRef, Q, Value
 from django.db.models.aggregates import Min
 from django.dispatch import receiver
+from django.utils.functional import cached_property
 from django.utils.timezone import make_aware, now
 from django.utils.translation import (
     gettext as _, gettext_lazy, ngettext_lazy, pgettext_lazy,
@@ -57,8 +58,8 @@ from pretix.base.decimal import round_decimal
 from pretix.base.i18n import language
 from pretix.base.media import MEDIA_TYPES
 from pretix.base.models import (
-    CartPosition, Event, InvoiceAddress, Item, ItemVariation, SalesChannel,
-    Seat, SeatCategoryMapping, Voucher,
+    CartPosition, Customer, Event, InvoiceAddress, Item, ItemVariation,
+    SalesChannel, Seat, SeatCategoryMapping, Voucher,
 )
 from pretix.base.models.event import SubEvent
 from pretix.base.models.orders import CheckoutSession, OrderFee
@@ -417,13 +418,15 @@ class CartManager:
     }
 
     def __init__(self, event: Event, cart_id: str, sales_channel: SalesChannel,
-                 invoice_address: InvoiceAddress=None, widget_data=None, reservation_time: timedelta=None):
+                 invoice_address: InvoiceAddress=None, widget_data=None, reservation_time: timedelta=None,
+                 customer: Customer=None):
         """
         Creates a new CartManager for an event.
         """
         self.event = event
         self.cart_id = cart_id
         self.real_now_dt = now()
+        self.customer = customer
         self._operations = []
         self._quota_diff = Counter()
         self._voucher_use_diff = Counter()
@@ -1544,7 +1547,7 @@ class CartManager:
             self._sales_channel.identifier,
             [
                 (cp.item_id, cp.subevent_id, cp.subevent.date_from if cp.subevent_id else None, cp.line_price_gross,
-                 cp.addon_to, cp.is_bundled, cp.listed_price - cp.price_after_voucher)
+                 cp.addon_to, cp.is_bundled, cp.listed_price - cp.price_after_voucher, cp.memberships_valid_by_time(self.memberships))
                 for cp in positions
             ]
         )
@@ -1559,6 +1562,13 @@ class CartManager:
 
         return diff
 
+    @cached_property
+    def memberships(self):
+        if self.customer:
+            return self.customer.memberships.filter(testmode=self.event.testmode).select_related('membership_type')
+        else:
+            return []
+
     def _remove_parents_if_bundles_are_removed(self):
         removed_positions = {op.position.pk for op in self._operations if isinstance(op, self.RemoveOperation)}
         for op in self._operations:
@@ -1712,7 +1722,8 @@ def get_fees(event, request, _total_ignored_=None, invoice_address=None, payment
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
 def add_items_to_cart(self, event: int, items: List[dict], cart_id: str=None, locale='en',
-                      invoice_address: int=None, widget_data=None, sales_channel='web', override_now_dt: datetime=None) -> None:
+                      invoice_address: int=None, widget_data=None, sales_channel='web', override_now_dt: datetime=None,
+                      customer: int=None) -> None:
     """
     Adds a list of items to a user's cart.
     :param event: The event ID in question
@@ -1734,10 +1745,16 @@ def add_items_to_cart(self, event: int, items: List[dict], cart_id: str=None, lo
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
 
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
+
         try:
             try:
                 cm = CartManager(event=event, cart_id=cart_id, invoice_address=ia, widget_data=widget_data,
-                                 sales_channel=sales_channel)
+                                 sales_channel=sales_channel, customer=customer)
                 cm.add_new_items(items)
                 cm.commit()
             except LockTimeoutException:
@@ -1747,7 +1764,7 @@ def add_items_to_cart(self, event: int, items: List[dict], cart_id: str=None, lo
 
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
-def apply_voucher(self, event: Event, voucher: str, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None) -> None:
+def apply_voucher(self, event: Event, voucher: str, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None, customer=None) -> None:
     """
     :param event: The event ID in question
     :param voucher: A voucher code
@@ -1758,9 +1775,14 @@ def apply_voucher(self, event: Event, voucher: str, cart_id: str=None, locale='e
             sales_channel = event.organizer.sales_channels.get(identifier=sales_channel)
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
         try:
             try:
-                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel)
+                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel, customer=customer)
                 cm.apply_voucher(voucher)
                 cm.commit()
             except LockTimeoutException:
@@ -1770,7 +1792,8 @@ def apply_voucher(self, event: Event, voucher: str, cart_id: str=None, locale='e
 
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
-def remove_cart_position(self, event: Event, position: int, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None) -> None:
+def remove_cart_position(self, event: Event, position: int, cart_id: str=None, locale='en',
+                         sales_channel='web', override_now_dt: datetime=None, customer=None) -> None:
     """
     Removes an item specified by its position ID from a user's cart.
     :param event: The event ID in question
@@ -1782,9 +1805,14 @@ def remove_cart_position(self, event: Event, position: int, cart_id: str=None, l
             sales_channel = event.organizer.sales_channels.get(identifier=sales_channel)
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
         try:
             try:
-                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel)
+                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel, customer=customer)
                 cm.remove_item(position)
                 cm.commit()
             except LockTimeoutException:
@@ -1794,7 +1822,7 @@ def remove_cart_position(self, event: Event, position: int, cart_id: str=None, l
 
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
-def clear_cart(self, event: Event, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None) -> None:
+def clear_cart(self, event: Event, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None, customer=None) -> None:
     """
     Removes all items from a user's cart.
     :param event: The event ID in question
@@ -1805,9 +1833,14 @@ def clear_cart(self, event: Event, cart_id: str=None, locale='en', sales_channel
             sales_channel = event.organizer.sales_channels.get(identifier=sales_channel)
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
         try:
             try:
-                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel)
+                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel, customer=customer)
                 cm.clear()
                 cm.commit()
             except LockTimeoutException:
@@ -1817,7 +1850,7 @@ def clear_cart(self, event: Event, cart_id: str=None, locale='en', sales_channel
 
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
-def extend_cart_reservation(self, event: Event, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None) -> dict:
+def extend_cart_reservation(self, event: Event, cart_id: str=None, locale='en', sales_channel='web', override_now_dt: datetime=None, customer=None) -> dict:
     """
     Resets the expiry time of a cart to the configured reservation time of this event.
     Limited to 11x the reservation time.
@@ -1830,9 +1863,14 @@ def extend_cart_reservation(self, event: Event, cart_id: str=None, locale='en',
             sales_channel = event.organizer.sales_channels.get(identifier=sales_channel)
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
         try:
             try:
-                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel)
+                cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel, customer=customer)
                 cm.commit()
                 return {
                     "success": cm.num_extended_positions,
@@ -1848,7 +1886,7 @@ def extend_cart_reservation(self, event: Event, cart_id: str=None, locale='en',
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(CartError,))
 def set_cart_addons(self, event: Event, addons: List[dict], add_to_cart_items: List[dict], cart_id: str=None, locale='en',
-                    invoice_address: int=None, sales_channel='web', override_now_dt: datetime=None) -> None:
+                    invoice_address: int=None, sales_channel='web', override_now_dt: datetime=None, customer=None) -> None:
     """
     Assigns addons to eligible products in a user's cart, adding and removing the addon products as necessary to
     ensure the requested addon state.
@@ -1869,9 +1907,14 @@ def set_cart_addons(self, event: Event, addons: List[dict], add_to_cart_items: L
             sales_channel = event.organizer.sales_channels.get(identifier=sales_channel)
         except SalesChannel.DoesNotExist:
             raise CartError("Invalid sales channel.")
+        if customer:
+            try:
+                customer = event.organizer.customers.get(pk=customer)
+            except Customer.DoesNotExist:
+                raise CartError("Invalid customer.")
         try:
             try:
-                cm = CartManager(event=event, cart_id=cart_id, invoice_address=ia, sales_channel=sales_channel)
+                cm = CartManager(event=event, cart_id=cart_id, invoice_address=ia, sales_channel=sales_channel, customer=customer)
                 cm.set_addons(addons)
                 cm.add_new_items(add_to_cart_items)
                 cm.commit()
diff --git a/src/pretix/base/services/cross_selling.py b/src/pretix/base/services/cross_selling.py
index 132ce5d0cb..57ba6e6303 100644
--- a/src/pretix/base/services/cross_selling.py
+++ b/src/pretix/base/services/cross_selling.py
@@ -112,6 +112,13 @@ class CrossSellingService:
             }
             return category.items.filter(pk__in=potential_discount_items), potential_discount_items
 
+    @cached_property
+    def memberships(self):
+        if self.customer:
+            return self.customer.memberships.filter(testmode=self.event.testmode).select_related('membership_type')
+        else:
+            return []
+
     @cached_property
     def _potential_discounts_by_subevent_and_item_for_current_cart(self):
         potential_discounts_by_cartpos = defaultdict(list)
@@ -123,7 +130,8 @@ class CrossSellingService:
             [
                 (cp.item_id, cp.subevent_id, cp.subevent.date_from if cp.subevent_id else None, cp.line_price_gross,
                  cp.addon_to, cp.is_bundled,
-                 cp.listed_price - cp.price_after_voucher)
+                 cp.listed_price - cp.price_after_voucher,
+                 cp.memberships_valid_by_time(self.memberships))
                 for cp in self.cartpositions
             ],
             collect_potential_discounts=potential_discounts_by_cartpos
diff --git a/src/pretix/base/services/orders.py b/src/pretix/base/services/orders.py
index 890fa06409..e25b23e625 100644
--- a/src/pretix/base/services/orders.py
+++ b/src/pretix/base/services/orders.py
@@ -56,7 +56,7 @@ from django.db.models import (
 from django.db.models.functions import Cast, Greatest
 from django.db.transaction import get_connection
 from django.dispatch import receiver
-from django.utils.functional import cached_property
+from django.utils.functional import cached_property, lazy
 from django.utils.timezone import make_aware, now
 from django.utils.translation import gettext as _, gettext_lazy, ngettext_lazy
 from django_scopes import scopes_disabled
@@ -923,12 +923,18 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
             continue
 
     sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]  # eliminate deleted
+
+    if customer:
+        memberships = lazy(lambda: list(customer.memberships.filter(testmode=event.testmode).select_related('membership_type')), list)()
+    else:
+        memberships = []
+
     discount_results = apply_discounts(
         event,
         sales_channel.identifier,
         [
             (cp.item_id, cp.subevent_id, cp.subevent.date_from if cp.subevent_id else None, cp.line_price_gross,
-             cp.addon_to, cp.is_bundled, cp.listed_price - cp.price_after_voucher)
+             cp.addon_to, cp.is_bundled, cp.listed_price - cp.price_after_voucher, cp.memberships_valid_by_time(memberships))
             for cp in sorted_positions
         ]
     )
diff --git a/src/pretix/base/services/pricing.py b/src/pretix/base/services/pricing.py
index cd332f157a..21fca82830 100644
--- a/src/pretix/base/services/pricing.py
+++ b/src/pretix/base/services/pricing.py
@@ -33,7 +33,7 @@ from django.db.models import Q
 from pretix.base.decimal import round_decimal
 from pretix.base.models import (
     AbstractPosition, CartPosition, InvoiceAddress, Item, ItemAddOn,
-    ItemVariation, OrderFee, OrderPosition, SalesChannel, Voucher,
+    ItemVariation, Membership, OrderFee, OrderPosition, SalesChannel, Voucher,
 )
 from pretix.base.models.discount import Discount, PositionInfo
 from pretix.base.models.event import Event, SubEvent
@@ -167,14 +167,15 @@ def get_line_price(price_after_voucher: Decimal, custom_price_input: Decimal, cu
 
 
 def apply_discounts(event: Event, sales_channel: Union[str, SalesChannel],
-                    positions: List[Tuple[int, Optional[int], Optional[datetime], Decimal, bool, bool, Decimal]],
+                    positions: List[Tuple[int, Optional[int], Optional[datetime], Decimal, bool, bool, Decimal, List[Membership]]],
                     collect_potential_discounts: Optional[defaultdict] = None) -> List[Tuple[Decimal, Optional[Discount]]]:
     """
     Applies any dynamic discounts to a cart
 
     :param event: Event the cart belongs to
     :param sales_channel: Sales channel the cart was created with
-    :param positions: Tuple of the form ``(item_id, subevent_id, subevent_date_from, line_price_gross, addon_to_id, is_bundled, voucher_discount)``
+    :param positions: Tuple of the form ``(item_id, subevent_id, subevent_date_from, line_price_gross, addon_to_id, is_bundled,
+                      voucher_discount, memberships_valid_by_time)``
                       ``addon_to_id`` does not have to be the proper ID, any identifier is okay, even ``True``/``False`` are accepted, but
                       a better result may be given if addons to the same main product have the same distinct value.
     :param collect_potential_discounts: If a `defaultdict(list)` is supplied, all discounts that could be applied to the cart
@@ -190,6 +191,17 @@ def apply_discounts(event: Event, sales_channel: Union[str, SalesChannel],
         sales_channel = sales_channel.identifier
     new_prices = {}
 
+    def _filter_memberships(memberships: List[Membership]) -> List[Membership]:
+        return [
+            # Currently unsupported configurations
+            m for m in memberships
+            if (
+                m.membership_type.max_usages is None and
+                m.membership_type.transferable and
+                m.membership_type.allow_parallel_usage
+            )
+        ]
+
     discount_qs = event.discounts.filter(
         Q(available_from__isnull=True) | Q(available_from__lte=time_machine_now()),
         Q(available_until__isnull=True) | Q(available_until__gte=time_machine_now()),
@@ -198,9 +210,11 @@ def apply_discounts(event: Event, sales_channel: Union[str, SalesChannel],
     ).prefetch_related('condition_limit_products', 'benefit_limit_products').order_by('position', 'pk')
     for discount in discount_qs:
         result = discount.apply({
-            idx: PositionInfo(item_id, subevent_id, subevent_date_from, line_price_gross, addon_to, voucher_discount)
+            idx: PositionInfo(item_id, subevent_id, subevent_date_from, line_price_gross, addon_to, voucher_discount,
+                              _filter_memberships(memberships_valid_by_time))
             for
-            idx, (item_id, subevent_id, subevent_date_from, line_price_gross, addon_to, is_bundled, voucher_discount)
+            idx, (item_id, subevent_id, subevent_date_from, line_price_gross, addon_to, is_bundled, voucher_discount,
+                  memberships_valid_by_time)
             in enumerate(positions)
             if not is_bundled and idx not in new_prices
         }, collect_potential_discounts)
diff --git a/src/pretix/control/forms/discounts.py b/src/pretix/control/forms/discounts.py
index 7f134c431e..3dde8b2449 100644
--- a/src/pretix/control/forms/discounts.py
+++ b/src/pretix/control/forms/discounts.py
@@ -22,7 +22,6 @@
 from decimal import Decimal
 
 from django import forms
-from django.utils.translation import gettext_lazy as _
 from django_scopes.forms import SafeModelMultipleChoiceField
 
 from pretix.base.channels import get_all_sales_channel_types
@@ -72,6 +71,7 @@ class DiscountForm(I18nModelForm):
             'condition_limit_products': ItemMultipleChoiceField,
             'benefit_limit_products': ItemMultipleChoiceField,
             'limit_sales_channels': SafeModelMultipleChoiceField,
+            'require_membership_types': SafeModelMultipleChoiceField,
         }
         widgets = {
             'subevent_mode': forms.RadioSelect,
@@ -91,6 +91,9 @@ class DiscountForm(I18nModelForm):
                     'data-display-dependency': '#id_condition_min_count',
                 }
             ),
+            'require_membership_types': forms.CheckboxSelectMultiple(attrs={
+                'class': 'scrolling-multiple-choice'
+            }),
         }
 
     def __init__(self, *args, **kwargs):
@@ -134,11 +137,5 @@ class DiscountForm(I18nModelForm):
         if d.get('condition_min_value') is None:
             d['condition_min_value'] = Decimal('0.00')
 
-        if d.get('require_membership') and not d.get('require_membership_types'):
-            self.add_error(
-                'require_membership_types',
-                _(
-                    "If a valid membership is required, at least one valid membership type needs to be selected."
-                )
-            )
+        Discount.validate_config(d)
         return d
diff --git a/src/pretix/control/templates/pretixcontrol/organizers/membershiptype_edit.html b/src/pretix/control/templates/pretixcontrol/organizers/membershiptype_edit.html
index 46705f58f2..adf7942afd 100644
--- a/src/pretix/control/templates/pretixcontrol/organizers/membershiptype_edit.html
+++ b/src/pretix/control/templates/pretixcontrol/organizers/membershiptype_edit.html
@@ -9,7 +9,23 @@
     {% endif %}
     <form class="form-horizontal" action="" method="post">
         {% csrf_token %}
-        {% bootstrap_form form layout="control" %}
+        {% bootstrap_form_errors form %}
+        <fieldset>
+            <legend>{% trans "General information" %}</legend>
+            {% bootstrap_field form.name layout="control" %}
+        </fieldset>
+        <fieldset>
+            <legend>{% trans "Usage restrictions" %}</legend>
+            <p>
+                {% blocktrans trimmed %}
+                    The following restrictions apply whenever the membership is used to buy a product or variation that
+                    is only available to membership holders.
+                {% endblocktrans %}
+            </p>
+            {% bootstrap_field form.transferable layout="control" %}
+            {% bootstrap_field form.allow_parallel_usage layout="control" %}
+            {% bootstrap_field form.max_usages layout="control" %}
+        </fieldset>
         <div class="form-group submit-group">
             <button type="submit" class="btn btn-primary btn-save">
                 {% trans "Save" %}
diff --git a/src/pretix/presale/checkoutflow.py b/src/pretix/presale/checkoutflow.py
index 8c9bab79f7..4f93de6dba 100644
--- a/src/pretix/presale/checkoutflow.py
+++ b/src/pretix/presale/checkoutflow.py
@@ -248,7 +248,19 @@ class TemplateFlowStep(TemplateResponseMixin, BaseCheckoutFlowStep):
         raise NotImplementedError()
 
 
-class CustomerStep(CartMixin, TemplateFlowStep):
+class RecomputeMixin:
+    def recompute_cart(self):
+        cm = CartManager(
+            event=self.request.event,
+            cart_id=get_or_create_cart_id(self.request),
+            invoice_address=self.invoice_address,
+            sales_channel=self.request.sales_channel,
+            customer=self.cart_customer,
+        )
+        return cm.recompute_final_prices_and_taxes()
+
+
+class CustomerStep(CartMixin, RecomputeMixin, TemplateFlowStep):
     priority = 45
     identifier = "customer"
     template_name = "pretixpresale/event/checkout_customer.html"
@@ -326,28 +338,34 @@ class CustomerStep(CartMixin, TemplateFlowStep):
         customer_login(self.request, customer)
         return True
 
+    def _proceed_to_next(self):
+        diff = self.recompute_cart()
+        if abs(diff) > Decimal('0.001'):
+            messages.info(self.request, _('Due to the information you entered, the total of your cart has changed.'))
+        return redirect_to_url(self.get_next_url(self.request))
+
     def post(self, request):
         self.request = request
 
         if request.POST.get("customer_mode") == 'login':
             if self.cart_session.get('customer'):
-                return redirect_to_url(self.get_next_url(request))
+                return self._proceed_to_next()
             elif request.customer:
                 self.cart_session['customer_mode'] = 'login'
                 self.cart_session['customer'] = request.customer.pk
                 self.cart_session['customer_cart_tied_to_login'] = True
-                return redirect_to_url(self.get_next_url(request))
+                return self._proceed_to_next()
             elif self.request.POST.get("login-sso-data"):
                 if not self._handle_sso_login():
                     messages.error(request, _('We failed to process your authentication request, please try again.'))
                     return self.render()
-                return redirect_to_url(self.get_next_url(request))
+                return self._proceed_to_next()
             elif self.event.settings.customer_accounts_native and self.login_form.is_valid():
                 customer_login(self.request, self.login_form.get_customer())
                 self.cart_session['customer_mode'] = 'login'
                 self.cart_session['customer'] = self.login_form.get_customer().pk
                 self.cart_session['customer_cart_tied_to_login'] = True
-                return redirect_to_url(self.get_next_url(request))
+                return self._proceed_to_next()
             else:
                 return self.render()
         elif request.POST.get("customer_mode") == 'register' and self.signup_allowed:
@@ -356,13 +374,13 @@ class CustomerStep(CartMixin, TemplateFlowStep):
                 self.cart_session['customer_mode'] = 'login'
                 self.cart_session['customer'] = customer.pk
                 self.cart_session['customer_cart_tied_to_login'] = False
-                return redirect_to_url(self.get_next_url(request))
+                return self._proceed_to_next()
             else:
                 return self.render()
         elif request.POST.get("customer_mode") == 'guest' and self.guest_allowed:
             self.cart_session['customer'] = None
             self.cart_session['customer_mode'] = 'guest'
-            return redirect_to_url(self.get_next_url(request))
+            return self._proceed_to_next()
         else:
             return self.render()
 
@@ -770,12 +788,18 @@ class AddOnsStep(CartMixin, AsyncAction, TemplateFlowStep):
 
         add_to_cart_items = _items_from_post_data(self.request, warn_if_empty=False)
 
+        if 'customer_mode' in self.cart_session:
+            cart_customer = self.cart_customer
+        else:
+            cart_customer = getattr(self.request, 'customer', None)
+
         return self.do(self.request.event.id, addons, add_to_cart_items, get_or_create_cart_id(self.request),
                        invoice_address=self.invoice_address.pk, locale=get_language(),
-                       sales_channel=request.sales_channel.identifier, override_now_dt=time_machine_now(default=None))
+                       sales_channel=request.sales_channel.identifier, override_now_dt=time_machine_now(default=None),
+                       customer=cart_customer.pk if cart_customer else None)
 
 
-class QuestionsStep(CartQuestionsViewMixin, CartMixin, TemplateFlowStep):
+class QuestionsStep(CartQuestionsViewMixin, RecomputeMixin, CartMixin, TemplateFlowStep):
     priority = 50
     identifier = "questions"
     template_name = "pretixpresale/event/checkout_questions.html"
@@ -986,6 +1010,7 @@ class QuestionsStep(CartQuestionsViewMixin, CartMixin, TemplateFlowStep):
     def post(self, request):
         self.request = request
         failed = not self.save() or not self.contact_form.is_valid()
+        recomputed = False
         if self.address_asked or self.request.event.settings.invoice_name_required:
             failed = failed or not self.invoice_form.is_valid()
         if failed:
@@ -1030,13 +1055,8 @@ class QuestionsStep(CartQuestionsViewMixin, CartMixin, TemplateFlowStep):
                 self.cart_session['saved_invoice_address'] = saved.pk
 
             try:
-                cm = CartManager(
-                    event=self.request.event,
-                    cart_id=get_or_create_cart_id(request),
-                    invoice_address=addr,
-                    sales_channel=request.sales_channel,
-                )
-                diff = cm.recompute_final_prices_and_taxes()
+                diff = self.recompute_cart()
+                recomputed = True
             except TaxRule.SaleNotAllowed:
                 messages.error(request,
                                _("Unfortunately, based on the invoice address you entered, we're not able to sell you "
@@ -1045,15 +1065,23 @@ class QuestionsStep(CartQuestionsViewMixin, CartMixin, TemplateFlowStep):
 
             self.cart_session['invoice_address'] = addr.pk
             if abs(diff) > Decimal('0.001'):
-                messages.info(request, _('Due to the invoice address you entered, we need to apply a different tax '
-                                         'rate to your purchase and the price of the products in your cart has '
-                                         'changed accordingly.'))
+                messages.info(request, _('Due to the information you entered, tax rates or discounts on your purchase '
+                                         'have been changed and  the price of the products in your cart has changed '
+                                         'accordingly.'))
                 return redirect_to_url(self.get_next_url(request) + '?open_cart=true')
         elif 'invoice_address' in self.cart_session:
             # Invoice address was there, but is no longer asked for
             self.invoice_address.delete()
             del self.cart_session['invoice_address']
 
+        if self.cart_customer and not recomputed and any(cp.item.validity_dynamic_start_choice for cp in self.positions):
+            # Discounts might have changed
+            diff = self.recompute_cart()
+            if abs(diff) > Decimal('0.001'):
+                messages.info(request, _('Due to the information you entered, tax rates or discounts on your purchase '
+                                         'have been changed and  the price of the products in your cart has changed '
+                                         'accordingly.'))
+
         try:
             validate_memberships_in_order(self.cart_customer, self.positions, self.request.event, lock=False,
                                           testmode=self.request.event.testmode, valid_from_not_chosen=False)
diff --git a/src/pretix/presale/productlist.py b/src/pretix/presale/productlist.py
index d8dfd90bee..4e00dc0643 100644
--- a/src/pretix/presale/productlist.py
+++ b/src/pretix/presale/productlist.py
@@ -32,7 +32,7 @@ from django.db.models.lookups import Exact
 
 from pretix.base.decimal import round_decimal
 from pretix.base.models import (
-    Discount, Event, Item, ItemVariation, Quota, SalesChannel,
+    Discount, Event, Item, ItemVariation, Membership, Quota, SalesChannel,
     SeatCategoryMapping, SubEvent, Voucher,
 )
 from pretix.base.models.items import (
@@ -58,7 +58,12 @@ def item_group_by_category(items):
 
 
 def _single_item_discounts(event: Event, sales_channel: Union[str, SalesChannel],
-                           subevent: SubEvent=None, voucher: Voucher=None, is_addons=False) -> List[Discount]:
+                           subevent: SubEvent=None, voucher: Voucher=None, is_addons=False,
+                           memberships: List[Membership]=None) -> List[Discount]:
+    if memberships is not None:
+        prefetch_membership_types = ['require_membership_types']
+    else:
+        prefetch_membership_types = []
     discount_qs = event.discounts.filter(
         Q(available_from__isnull=True) | Q(available_from__lte=time_machine_now()),
         Q(available_until__isnull=True) | Q(available_until__gte=time_machine_now()),
@@ -69,7 +74,7 @@ def _single_item_discounts(event: Event, sales_channel: Union[str, SalesChannel]
         benefit_same_products=True,
         condition_min_value=Decimal("0.00"),
         condition_min_count=1,
-    ).prefetch_related('condition_limit_products').order_by('position', 'pk')
+    ).prefetch_related('condition_limit_products', *prefetch_membership_types).order_by('position', 'pk')
 
     if subevent:
         discount_qs = discount_qs.filter(
@@ -236,6 +241,7 @@ def prepare_item_list_for_shop(event, *, channel: SalesChannel, subevent=None, v
             voucher=voucher,
             subevent=subevent,
             is_addons=allow_addons,
+            memberships=memberships,
         ))
     discounts = _discount_cache[cache_key]
 
@@ -322,7 +328,8 @@ def prepare_item_list_for_shop(event, *, channel: SalesChannel, subevent=None, v
                 item.description += ("<br/>" if item.description else "") + resp
 
         matching_discounts = [
-            d for d in discounts if d.condition_all_products or item in d.condition_limit_products.all()
+            d for d in discounts
+            if d.condition_matches_product(item) and d.valid_for_memberships(memberships, event, subevent, item)
         ]
 
         if not item.has_variations:
diff --git a/src/pretix/presale/views/cart.py b/src/pretix/presale/views/cart.py
index 6285c67fc1..f7cc5eb3af 100644
--- a/src/pretix/presale/views/cart.py
+++ b/src/pretix/presale/views/cart.py
@@ -58,7 +58,8 @@ from django.views.generic import TemplateView, View
 from django_scopes import scopes_disabled
 
 from pretix.base.models import (
-    CartPosition, GiftCard, InvoiceAddress, QuestionAnswer, SubEvent, Voucher,
+    CartPosition, Customer, GiftCard, InvoiceAddress, QuestionAnswer, SubEvent,
+    Voucher,
 )
 from pretix.base.services.cart import (
     CartError, add_items_to_cart, apply_voucher, clear_cart, error_messages,
@@ -153,6 +154,17 @@ class CartActionMixin:
         except InvoiceAddress.DoesNotExist:
             return InvoiceAddress()
 
+    @cached_property
+    def cart_customer(self):
+        if 'customer_mode' in self.cart_session:
+            if self.cart_session['customer_mode'] == 'login':
+                try:
+                    return self.request.organizer.customers.get(pk=self.cart_session.get('customer', -1))
+                except Customer.DoesNotExist:
+                    return
+        else:
+            return getattr(self.request, 'customer', None)
+
 
 def _item_from_post_value(request, key, value, voucher=None, voucher_ignore_if_redeemed=False):
     if value.strip() == '' or '_' not in key:
@@ -505,7 +517,7 @@ class CartApplyVoucher(EventViewMixin, CartActionMixin, AsyncAction, View):
 
             return self.do(self.request.event.id, code, get_or_create_cart_id(self.request),
                            translation.get_language(), request.sales_channel.identifier,
-                           time_machine_now(default=None))
+                           time_machine_now(default=None), self.cart_customer.pk if self.cart_customer else None)
         else:
             if 'ajax' in self.request.GET or 'ajax' in self.request.POST:
                 return JsonResponse({
@@ -532,7 +544,7 @@ class CartRemove(EventViewMixin, CartActionMixin, AsyncAction, View):
             try:
                 return self.do(self.request.event.id, int(request.POST.get('id')), get_or_create_cart_id(self.request),
                                translation.get_language(), request.sales_channel.identifier,
-                               time_machine_now(default=None))
+                               time_machine_now(default=None), self.cart_customer.pk if self.cart_customer else None)
             except ValueError:
                 return redirect_to_url(self.get_error_url())
         else:
@@ -555,7 +567,7 @@ class CartClear(EventViewMixin, CartActionMixin, AsyncAction, View):
 
     def post(self, request, *args, **kwargs):
         return self.do(self.request.event.id, get_or_create_cart_id(self.request), translation.get_language(),
-                       request.sales_channel.identifier, time_machine_now(default=None))
+                       request.sales_channel.identifier, time_machine_now(default=None), self.cart_customer.pk if self.cart_customer else None)
 
 
 @method_decorator(allow_cors_if_namespaced, 'dispatch')
@@ -591,7 +603,7 @@ class CartExtendReservation(EventViewMixin, CartActionMixin, AsyncAction, View):
 
     def post(self, request, *args, **kwargs):
         return self.do(self.request.event.id, get_or_create_cart_id(self.request), translation.get_language(),
-                       request.sales_channel.identifier, time_machine_now(default=None))
+                       request.sales_channel.identifier, time_machine_now(default=None), self.cart_customer.pk if self.cart_customer else None)
 
 
 @method_decorator(allow_cors_if_namespaced, 'dispatch')
@@ -648,7 +660,7 @@ class CartAdd(EventViewMixin, CartActionMixin, AsyncAction, View):
         if items:
             return self.do(self.request.event.id, items, cart_id, translation.get_language(),
                            self.invoice_address.pk, widget_data, self.request.sales_channel.identifier,
-                           time_machine_now(default=None))
+                           time_machine_now(default=None), self.cart_customer.pk if self.cart_customer else None)
         else:
             if 'ajax' in self.request.GET or 'ajax' in self.request.POST:
                 return JsonResponse({