diff --git a/src/pretix/base/services/cart.py b/src/pretix/base/services/cart.py
index 1fe05491d5..8984622b58 100644
--- a/src/pretix/base/services/cart.py
+++ b/src/pretix/base/services/cart.py
@@ -97,6 +97,10 @@ class CartError(Exception):
         super().__init__(msg)
 
 
+class CartPositionError(CartError):
+    pass
+
+
 error_messages = {
     'busy': gettext_lazy(
         'We were not able to process your request completely as the '
@@ -106,6 +110,9 @@ error_messages = {
     'unknown_position': gettext_lazy('Unknown cart position.'),
     'subevent_required': pgettext_lazy('subevent', 'No date was specified.'),
     'not_for_sale': gettext_lazy('You selected a product which is not available for sale.'),
+    'positions_removed': gettext_lazy(
+        'Some products can no longer be purchased and have been removed from your cart for the following reason: %s'
+    ),
     'unavailable': gettext_lazy(
         'Some of the products you selected are no longer available. '
         'Please see below for details.'
@@ -258,6 +265,138 @@ def _get_voucher_availability(event, voucher_use_diff, now_dt, exclude_position_
     return vouchers_ok, _voucher_depend_on_cart
 
 
+def _check_position_constraints(
+    event: Event, item: Item, variation: ItemVariation, voucher: Voucher, subevent: SubEvent,
+    seat: Seat, sales_channel: SalesChannel, already_in_cart: bool, cart_is_expired: bool, real_now_dt: datetime,
+    item_requires_seat: bool, is_addon: bool, is_bundled: bool,
+):
+    """
+    Checks if a cart position with the given constraints can still be sold. This checks configuration and time-based
+    constraints of item, subevent, and voucher.
+
+    It does NOT
+    - check if quota/voucher/seat are still available
+    - check prices
+    - check memberships
+    - perform any checks that go beyond the single line (like item.max_per_order)
+    """
+    time_machine_now_dt = time_machine_now(real_now_dt)
+    # Item or variation disabled
+    # Item disabled or unavailable by time
+    if not item.is_available(time_machine_now_dt) or (variation and not variation.is_available(time_machine_now_dt)):
+        raise CartPositionError(error_messages['unavailable'])
+
+    # Invalid media policy for online sale
+    if item.media_policy in (Item.MEDIA_POLICY_NEW, Item.MEDIA_POLICY_REUSE_OR_NEW):
+        mt = MEDIA_TYPES[item.media_type]
+        if not mt.medium_created_by_server:
+            raise CartPositionError(error_messages['media_usage_not_implemented'])
+    elif item.media_policy == Item.MEDIA_POLICY_REUSE:
+        raise CartPositionError(error_messages['media_usage_not_implemented'])
+
+    # Item removed from sales channel
+    if not item.all_sales_channels:
+        if sales_channel.identifier not in (s.identifier for s in item.limit_sales_channels.all()):
+            raise CartPositionError(error_messages['unavailable'])
+
+    # Variation removed from sales channel
+    if variation and not variation.all_sales_channels:
+        if sales_channel.identifier not in (s.identifier for s in variation.limit_sales_channels.all()):
+            raise CartPositionError(error_messages['unavailable'])
+
+    # Item disabled or unavailable by time in subevent
+    if subevent and item.pk in subevent.item_overrides and not subevent.item_overrides[item.pk].is_available(time_machine_now_dt):
+        raise CartPositionError(error_messages['not_for_sale'])
+
+    # Variation disabled or unavailable by time in subevent
+    if subevent and variation and variation.pk in subevent.var_overrides and \
+            not subevent.var_overrides[variation.pk].is_available(time_machine_now_dt):
+        raise CartPositionError(error_messages['not_for_sale'])
+
+    # Item requires a variation (should never happen)
+    if item.has_variations and not variation:
+        raise CartPositionError(error_messages['not_for_sale'])
+
+    # Variation belongs to wrong item (should never happen)
+    if variation and variation.item_id != item.pk:
+        raise CartPositionError(error_messages['not_for_sale'])
+
+    # Voucher does not apply to product
+    if voucher and not voucher.applies_to(item, variation):
+        raise CartPositionError(error_messages['voucher_invalid_item'])
+
+    # Voucher does not apply to seat
+    if voucher and voucher.seat and voucher.seat != seat:
+        raise CartPositionError(error_messages['voucher_invalid_seat'])
+
+    # Voucher does not apply to subevent
+    if voucher and voucher.subevent_id and voucher.subevent_id != subevent.pk:
+        raise CartPositionError(error_messages['voucher_invalid_subevent'])
+
+    # Voucher expired
+    if voucher and voucher.valid_until and voucher.valid_until < time_machine_now_dt:
+        raise CartPositionError(error_messages['voucher_expired'])
+
+    # Subevent has been disabled
+    if subevent and not subevent.active:
+        raise CartPositionError(error_messages['inactive_subevent'])
+
+    # Subevent sale not started
+    if subevent and subevent.effective_presale_start and time_machine_now_dt < subevent.effective_presale_start:
+        raise CartPositionError(error_messages['not_started'])
+
+    # Subevent sale has ended
+    if subevent and subevent.presale_has_ended:
+        raise CartPositionError(error_messages['ended'])
+
+    # Payment for subevent no longer possible
+    if subevent:
+        tlv = event.settings.get('payment_term_last', as_type=RelativeDateWrapper)
+        if tlv:
+            term_last = make_aware(datetime.combine(
+                tlv.datetime(subevent).date(),
+                time(hour=23, minute=59, second=59)
+            ), event.timezone)
+            if term_last < time_machine_now_dt:
+                raise CartPositionError(error_messages['payment_ended'])
+
+    # Seat required but no seat given
+    if item_requires_seat and not seat:
+        raise CartPositionError(error_messages['seat_invalid'])
+
+    # Seat given but no seat required
+    if seat and not item_requires_seat:
+        raise CartPositionError(error_messages['seat_forbidden'])
+
+    # Item requires to be add-on but is top-level position
+    if item.category and item.category.is_addon and not is_addon:
+        raise CartPositionError(error_messages['addon_only'])
+
+    # Item requires bundling but is top-level position
+    if item.require_bundling and not is_bundled:
+        raise CartPositionError(error_messages['bundled_only'])
+
+    # Seat for wrong product
+    if seat and seat.product != item:
+        raise CartPositionError(error_messages['seat_invalid'])
+
+    # Seat blocked
+    if seat and seat.blocked and sales_channel.identifier not in event.settings.seating_allow_blocked_seats_for_channel:
+        raise CartPositionError(error_messages['seat_invalid'])
+
+    # Item requires voucher but no voucher given
+    if item.require_voucher and voucher is None and not is_bundled:
+        raise CartPositionError(error_messages['voucher_required'])
+
+    # Item or variation is hidden without voucher but no voucher is given
+    if (
+        (item.hide_without_voucher or (variation and variation.hide_without_voucher)) and
+        (voucher is None or not voucher.show_hidden_items) and
+        not is_bundled
+    ):
+        raise CartPositionError(error_messages['voucher_required'])
+
+
 class CartManager:
     AddOperation = namedtuple('AddOperation', ('count', 'item', 'variation', 'voucher', 'quotas',
                                                'addon_to', 'subevent', 'bundled', 'seat', 'listed_price',
@@ -294,6 +433,7 @@ class CartManager:
         self._widget_data = widget_data or {}
         self._sales_channel = sales_channel
         self.num_extended_positions = 0
+        self.price_change_for_extended = False
 
         if reservation_time:
             self._reservation_time = reservation_time
@@ -421,14 +561,14 @@ class CartManager:
             if cartsize > limit:
                 raise CartError(error_messages['max_items'] % limit)
 
-    def _check_item_constraints(self, op, current_ops=[]):
+    def _check_item_constraints(self, op):
         if isinstance(op, (self.AddOperation, self.ExtendOperation)):
             if not (
                 (isinstance(op, self.AddOperation) and op.addon_to == 'FAKE') or
                 (isinstance(op, self.ExtendOperation) and op.position.is_bundled)
             ):
                 if op.item.require_voucher and op.voucher is None:
-                    if getattr(op, 'voucher_ignored', False):
+                    if getattr(op, 'voucher_ignored', False):  # todo??
                         raise CartError(error_messages['voucher_redeemed'])
                     raise CartError(error_messages['voucher_required'])
 
@@ -440,88 +580,39 @@ class CartManager:
                         raise CartError(error_messages['voucher_redeemed'])
                     raise CartError(error_messages['voucher_required'])
 
-            if not op.item.is_available() or (op.variation and not op.variation.is_available()):
-                raise CartError(error_messages['unavailable'])
-
-            if op.item.media_policy in (Item.MEDIA_POLICY_NEW, Item.MEDIA_POLICY_REUSE_OR_NEW):
-                mt = MEDIA_TYPES[op.item.media_type]
-                if not mt.medium_created_by_server:
-                    raise CartError(error_messages['media_usage_not_implemented'])
-            elif op.item.media_policy == Item.MEDIA_POLICY_REUSE:
-                raise CartError(error_messages['media_usage_not_implemented'])
-
-            if not op.item.all_sales_channels:
-                if self._sales_channel.identifier not in (s.identifier for s in op.item.limit_sales_channels.all()):
-                    raise CartError(error_messages['unavailable'])
-
-            if op.variation and not op.variation.all_sales_channels:
-                if self._sales_channel.identifier not in (s.identifier for s in op.variation.limit_sales_channels.all()):
-                    raise CartError(error_messages['unavailable'])
-
-            if op.subevent and op.item.pk in op.subevent.item_overrides and not op.subevent.item_overrides[op.item.pk].is_available():
-                raise CartError(error_messages['not_for_sale'])
-
-            if op.subevent and op.variation and op.variation.pk in op.subevent.var_overrides and \
-                    not op.subevent.var_overrides[op.variation.pk].is_available():
-                raise CartError(error_messages['not_for_sale'])
-
-            if op.item.has_variations and not op.variation:
-                raise CartError(error_messages['not_for_sale'])
-
-            if op.variation and op.variation.item_id != op.item.pk:
-                raise CartError(error_messages['not_for_sale'])
-
-            if op.voucher and not op.voucher.applies_to(op.item, op.variation):
-                raise CartError(error_messages['voucher_invalid_item'])
-
-            if op.voucher and op.voucher.seat and op.voucher.seat != op.seat:
-                raise CartError(error_messages['voucher_invalid_seat'])
-
-            if op.voucher and op.voucher.subevent_id and op.voucher.subevent_id != op.subevent.pk:
-                raise CartError(error_messages['voucher_invalid_subevent'])
-
-            if op.subevent and not op.subevent.active:
-                raise CartError(error_messages['inactive_subevent'])
-
-            if op.subevent and op.subevent.presale_start and time_machine_now(self.real_now_dt) < op.subevent.presale_start:
-                raise CartError(error_messages['not_started'])
-
-            if op.subevent and op.subevent.presale_has_ended:
-                raise CartError(error_messages['ended'])
-
-            seated = self._is_seated(op.item, op.subevent)
-            if (
-                seated and (
-                    not op.seat or (
-                        op.seat.blocked and
-                        self._sales_channel.identifier not in self.event.settings.seating_allow_blocked_seats_for_channel
-                    )
-                )
-            ):
-                raise CartError(error_messages['seat_invalid'])
-            elif op.seat and not seated:
-                raise CartError(error_messages['seat_forbidden'])
-            elif op.seat and op.seat.product != op.item:
-                raise CartError(error_messages['seat_invalid'])
-            elif op.seat and op.count > 1:
+            if op.seat and op.count > 1:
                 raise CartError('Invalid request: A seat can only be bought once.')
 
-            if op.subevent:
-                tlv = self.event.settings.get('payment_term_last', as_type=RelativeDateWrapper)
-                if tlv:
-                    term_last = make_aware(datetime.combine(
-                        tlv.datetime(op.subevent).date(),
-                        time(hour=23, minute=59, second=59)
-                    ), self.event.timezone)
-                    if term_last < time_machine_now(self.real_now_dt):
-                        raise CartError(error_messages['payment_ended'])
+            if isinstance(op, self.AddOperation):
+                is_addon = op.addon_to
+                is_bundled = op.addon_to == "FAKE"
+            else:
+                is_addon = op.position.addon_to
+                is_bundled = op.position.is_bundled
 
-        if isinstance(op, self.AddOperation):
-            if op.item.category and op.item.category.is_addon and not (op.addon_to and op.addon_to != 'FAKE'):
-                raise CartError(error_messages['addon_only'])
-
-            if op.item.require_bundling and not op.addon_to == 'FAKE':
-                raise CartError(error_messages['bundled_only'])
+            try:
+                _check_position_constraints(
+                    event=self.event,
+                    item=op.item,
+                    variation=op.variation,
+                    voucher=op.voucher,
+                    subevent=op.subevent,
+                    seat=op.seat,
+                    sales_channel=self._sales_channel,
+                    already_in_cart=isinstance(op, self.ExtendOperation),
+                    cart_is_expired=isinstance(op, self.ExtendOperation),
+                    real_now_dt=self.real_now_dt,
+                    item_requires_seat=self._is_seated(op.item, op.subevent),
+                    is_addon=is_addon,
+                    is_bundled=is_bundled,
+                )
+                # Quota, seat, and voucher availability is checked for in perform_operations
+                # Price changes are checked for in extend_expired_positions
+            except CartPositionError as e:
+                if e.args[0] == error_messages['voucher_required'] and getattr(op, 'voucher_ignored', False):
+                    # This is the case where someone clicks +1 on a voucher-only item with a fully redeemed voucher:
+                    raise CartPositionError(error_messages['voucher_redeemed'])
+                raise
 
     def _get_price(self, item: Item, variation: Optional[ItemVariation],
                    voucher: Optional[Voucher], custom_price: Optional[Decimal],
@@ -604,7 +695,11 @@ class CartManager:
                 quotas=quotas, subevent=cp.subevent, seat=cp.seat, listed_price=listed_price,
                 price_after_voucher=price_after_voucher,
             )
-            self._check_item_constraints(op)
+            try:
+                self._check_item_constraints(op)
+            except CartPositionError as e:
+                self._operations.append(self.RemoveOperation(position=cp))
+                err = error_messages['positions_removed'] % str(e)
 
             if cp.voucher:
                 self._voucher_use_diff[cp.voucher] += 2
@@ -797,7 +892,7 @@ class CartManager:
                     custom_price_input_is_net=False,
                     voucher_ignored=False,
                 )
-                self._check_item_constraints(bop, operations)
+                self._check_item_constraints(bop)
                 bundled.append(bop)
 
             listed_price = get_listed_price(item, variation, subevent)
@@ -836,7 +931,7 @@ class CartManager:
                 custom_price_input_is_net=self.event.settings.display_net_prices,
                 voucher_ignored=voucher_ignored,
             )
-            self._check_item_constraints(op, operations)
+            self._check_item_constraints(op)
             operations.append(op)
 
         self._quota_diff.update(quota_diff)
@@ -975,7 +1070,7 @@ class CartManager:
                     custom_price_input_is_net=self.event.settings.display_net_prices,
                     voucher_ignored=False,
                 )
-                self._check_item_constraints(op, operations)
+                self._check_item_constraints(op)
                 operations.append(op)
 
         # Check constraints on the add-on combinations
@@ -1172,7 +1267,9 @@ class CartManager:
                 op.position.delete()
 
             elif isinstance(op, (self.AddOperation, self.ExtendOperation)):
-                # Create a CartPosition for as much items as we can
+                if isinstance(op, self.ExtendOperation) and (op.position.pk in deleted_positions or not op.position.pk):
+                    continue  # Already deleted in other operation
+                # Create a CartPosition for as many items as we can
                 requested_count = quota_available_count = voucher_available_count = op.count
 
                 if op.seat:
@@ -1343,6 +1440,8 @@ class CartManager:
                         addons.delete()
                         op.position.delete()
                     elif available_count == 1:
+                        if op.price_after_voucher != op.position.price_after_voucher:
+                            self.price_change_for_extended = True
                         op.position.expires = self._expiry
                         op.position.max_extend = self._max_expiry_extend
                         op.position.listed_price = op.listed_price
@@ -1444,6 +1543,14 @@ class CartManager:
 
         return diff
 
+    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:
+            if isinstance(op, self.RemoveOperation):
+                if op.position.is_bundled and op.position.addon_to_id not in removed_positions:
+                    self._operations.append(self.RemoveOperation(position=op.position.addon_to))
+                    removed_positions.add(op.position.addon_to_id)
+
     def commit(self):
         self._check_presale_dates()
         self._check_max_cart_size()
@@ -1453,6 +1560,7 @@ class CartManager:
         err = err or self._check_min_per_voucher()
 
         self._extend_expiry_of_valid_existing_positions()
+        self._remove_parents_if_bundles_are_removed()
         err = self._perform_operations() or err
         self.recompute_final_prices_and_taxes()
 
@@ -1708,7 +1816,12 @@ def extend_cart_reservation(self, event: Event, cart_id: str=None, locale='en',
             try:
                 cm = CartManager(event=event, cart_id=cart_id, sales_channel=sales_channel)
                 cm.commit()
-                return {"success": cm.num_extended_positions, "expiry": cm._expiry, "max_expiry_extend": cm._max_expiry_extend}
+                return {
+                    "success": cm.num_extended_positions,
+                    "expiry": cm._expiry,
+                    "max_expiry_extend": cm._max_expiry_extend,
+                    "price_changed": cm.price_change_for_extended,
+                }
             except LockTimeoutException:
                 self.retry()
         except (MaxRetriesExceededError, LockTimeoutException):
diff --git a/src/pretix/base/services/orders.py b/src/pretix/base/services/orders.py
index e8be424cf5..e8b4bf9411 100644
--- a/src/pretix/base/services/orders.py
+++ b/src/pretix/base/services/orders.py
@@ -81,7 +81,7 @@ from pretix.base.models.tax import TAXED_ZERO, TaxedPrice, TaxRule
 from pretix.base.payment import GiftCardPayment, PaymentException
 from pretix.base.reldate import RelativeDateWrapper
 from pretix.base.secrets import assign_ticket_secret
-from pretix.base.services import tickets
+from pretix.base.services import cart, tickets
 from pretix.base.services.invoices import (
     generate_cancellation, generate_invoice, invoice_qualified,
     invoice_transmission_separately, order_invoice_transmission_separately,
@@ -130,6 +130,9 @@ class OrderError(Exception):
 
 
 error_messages = {
+    'positions_removed': gettext_lazy(
+        'Some products can no longer be purchased and have been removed from your cart for the following reason: %s'
+    ),
     'unavailable': gettext_lazy(
         'Some of the products you selected were no longer available. '
         'Please see below for details.'
@@ -182,14 +185,6 @@ error_messages = {
         'The voucher code used for one of the items in your cart is not valid for this item. We removed this item from your cart.'
     ),
     'voucher_required': gettext_lazy('You need a valid voucher code to order one of the products.'),
-    'some_subevent_not_started': gettext_lazy(
-        'The booking period for one of the events in your cart has not yet started. The '
-        'affected positions have been removed from your cart.'
-    ),
-    'some_subevent_ended': gettext_lazy(
-        'The booking period for one of the events in your cart has ended. The affected '
-        'positions have been removed from your cart.'
-    ),
     'seat_invalid': gettext_lazy('One of the seats in your order was invalid, we removed the position from your cart.'),
     'seat_unavailable': gettext_lazy('One of the seats in your order has been taken in the meantime, we removed the position from your cart.'),
     'country_blocked': gettext_lazy('One of the selected products is not available in the selected country.'),
@@ -744,12 +739,37 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
             deleted_positions.add(cp.pk)
             cp.delete()
 
-    sorted_positions = sorted(positions, key=lambda c: (-int(c.is_bundled), c.pk))
+    sorted_positions = list(sorted(positions, key=lambda c: (-int(c.is_bundled), c.pk)))
 
     for cp in sorted_positions:
         cp._cached_quotas = list(cp.quotas)
 
+    for cp in sorted_positions:
+        try:
+            cart._check_position_constraints(
+                event=event,
+                item=cp.item,
+                variation=cp.variation,
+                voucher=cp.voucher,
+                subevent=cp.subevent,
+                seat=cp.seat,
+                sales_channel=sales_channel,
+                already_in_cart=True,
+                cart_is_expired=cp.expires < now_dt,
+                real_now_dt=now_dt,
+                item_requires_seat=cp.requires_seat,
+                is_addon=bool(cp.addon_to_id),
+                is_bundled=bool(cp.addon_to_id) and cp.is_bundled,
+            )
+            # Quota, seat, and voucher availability is checked for below
+            # Prices are checked for below
+            # Memberships are checked in _create_order
+        except cart.CartPositionError as e:
+            err = error_messages['positions_removed'] % str(e)
+            delete(cp)
+
     # Create locks
+    sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]  # eliminate deleted
     if any(cp.expires < now() + timedelta(seconds=LOCK_TRUST_WINDOW) for cp in sorted_positions):
         # No need to perform any locking if the cart positions still guarantee everything long enough.
         full_lock_required = any(
@@ -774,15 +794,12 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
 
     # Check availability
     for i, cp in enumerate(sorted_positions):
-        if cp.pk in deleted_positions:
+        if cp.pk in deleted_positions or not cp.pk:
             continue
 
-        if not cp.item.is_available() or (cp.variation and not cp.variation.is_available()):
-            err = err or error_messages['unavailable']
-            delete(cp)
-            continue
         quotas = cp._cached_quotas
 
+        # Product per order limits
         products_seen[cp.item] += 1
         if cp.item.max_per_order and products_seen[cp.item] > cp.item.max_per_order:
             err = error_messages['max_items_per_product'] % {
@@ -792,6 +809,7 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
             delete(cp)
             break
 
+        # Voucher availability
         if cp.voucher:
             v_usages[cp.voucher] += 1
             if cp.voucher not in v_avail:
@@ -806,48 +824,14 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
                 delete(cp)
                 continue
 
-        if cp.subevent and cp.subevent.presale_start and time_machine_now_dt < cp.subevent.presale_start:
-            err = err or error_messages['some_subevent_not_started']
-            delete(cp)
-            break
-
-        if cp.subevent:
-            tlv = event.settings.get('payment_term_last', as_type=RelativeDateWrapper)
-            if tlv:
-                term_last = make_aware(datetime.combine(
-                    tlv.datetime(cp.subevent).date(),
-                    time(hour=23, minute=59, second=59)
-                ), event.timezone)
-                if term_last < time_machine_now_dt:
-                    err = err or error_messages['some_subevent_ended']
-                    delete(cp)
-                    break
-
-        if cp.subevent and cp.subevent.presale_has_ended:
-            err = err or error_messages['some_subevent_ended']
-            delete(cp)
-            break
-
-        if (cp.requires_seat and not cp.seat) or (cp.seat and not cp.requires_seat) or (cp.seat and cp.seat.product != cp.item) or cp.seat in seats_seen:
+        # Check duplicate seats in order
+        if cp.seat in seats_seen:
             err = err or error_messages['seat_invalid']
             delete(cp)
             break
+
         if cp.seat:
             seats_seen.add(cp.seat)
-
-        if cp.item.require_voucher and cp.voucher is None and not cp.is_bundled:
-            delete(cp)
-            err = err or error_messages['voucher_required']
-            break
-
-        if (cp.item.hide_without_voucher or (cp.variation and cp.variation.hide_without_voucher)) and (
-                cp.voucher is None or not cp.voucher.show_hidden_items or not cp.voucher.applies_to(cp.item, cp.variation)
-        ) and not cp.is_bundled:
-            delete(cp)
-            err = error_messages['voucher_required']
-            break
-
-        if cp.seat:
             # Unlike quotas (which we blindly trust as long as the position is not expired), we check seats every
             # time, since we absolutely can not overbook a seat.
             if not cp.seat.is_available(ignore_cart=cp, ignore_voucher_id=cp.voucher_id, sales_channel=sales_channel.identifier):
@@ -855,34 +839,13 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
                 delete(cp)
                 continue
 
-        if cp.expires >= now_dt and not cp.voucher:
-            # Other checks are not necessary
-            continue
-
+        # Check useful quota configuration
         if len(quotas) == 0:
             err = err or error_messages['unavailable']
             delete(cp)
             continue
 
-        if cp.subevent and cp.item.pk in cp.subevent.item_overrides and not cp.subevent.item_overrides[cp.item.pk].is_available(time_machine_now_dt):
-            err = err or error_messages['unavailable']
-            delete(cp)
-            continue
-
-        if cp.subevent and cp.variation and cp.variation.pk in cp.subevent.var_overrides and \
-                not cp.subevent.var_overrides[cp.variation.pk].is_available(time_machine_now_dt):
-            err = err or error_messages['unavailable']
-            delete(cp)
-            continue
-
-        if cp.voucher:
-            if cp.voucher.valid_until and cp.voucher.valid_until < time_machine_now_dt:
-                err = err or error_messages['voucher_expired']
-                delete(cp)
-                continue
-
         quota_ok = True
-
         ignore_all_quotas = cp.expires >= now_dt or (
             cp.voucher and (
                 cp.voucher.allow_ignore_quota or (cp.voucher.block_quota and cp.voucher.quota is None)
@@ -914,7 +877,7 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
             })
 
     # Check prices
-    sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]
+    sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]  # eliminate deleted
     old_total = sum(cp.price for cp in sorted_positions)
     for i, cp in enumerate(sorted_positions):
         if cp.listed_price is None:
@@ -945,7 +908,7 @@ def _check_positions(event: Event, now_dt: datetime, time_machine_now_dt: dateti
             delete(cp)
             continue
 
-    sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]
+    sorted_positions = [cp for cp in sorted_positions if cp.pk and cp.pk not in deleted_positions]  # eliminate deleted
     discount_results = apply_discounts(
         event,
         sales_channel.identifier,
diff --git a/src/pretix/presale/views/cart.py b/src/pretix/presale/views/cart.py
index b9cfebd41a..892719f67e 100644
--- a/src/pretix/presale/views/cart.py
+++ b/src/pretix/presale/views/cart.py
@@ -435,7 +435,7 @@ def cart_session(request):
 @method_decorator(allow_frame_if_namespaced, 'dispatch')
 class CartApplyVoucher(EventViewMixin, CartActionMixin, AsyncAction, View):
     task = apply_voucher
-    known_errortypes = ['CartError']
+    known_errortypes = ['CartError', 'CartPositionError']
 
     def get_success_message(self, value):
         return _('We applied the voucher to as many products in your cart as we could.')
@@ -513,7 +513,7 @@ class CartApplyVoucher(EventViewMixin, CartActionMixin, AsyncAction, View):
 @method_decorator(allow_frame_if_namespaced, 'dispatch')
 class CartRemove(EventViewMixin, CartActionMixin, AsyncAction, View):
     task = remove_cart_position
-    known_errortypes = ['CartError']
+    known_errortypes = ['CartError', 'CartPositionError']
 
     def get_success_message(self, value):
         if CartPosition.objects.filter(cart_id=get_or_create_cart_id(self.request)).exists():
@@ -542,7 +542,7 @@ class CartRemove(EventViewMixin, CartActionMixin, AsyncAction, View):
 @method_decorator(allow_frame_if_namespaced, 'dispatch')
 class CartClear(EventViewMixin, CartActionMixin, AsyncAction, View):
     task = clear_cart
-    known_errortypes = ['CartError']
+    known_errortypes = ['CartError', 'CartPositionError']
 
     def get_success_message(self, value):
         create_empty_cart_id(self.request)
@@ -556,7 +556,7 @@ class CartClear(EventViewMixin, CartActionMixin, AsyncAction, View):
 @method_decorator(allow_frame_if_namespaced, 'dispatch')
 class CartExtendReservation(EventViewMixin, CartActionMixin, AsyncAction, View):
     task = extend_cart_reservation
-    known_errortypes = ['CartError']
+    known_errortypes = ['CartError', 'CartPositionError']
 
     def _ajax_response_data(self, value):
         if isinstance(value, dict):
@@ -566,7 +566,11 @@ class CartExtendReservation(EventViewMixin, CartActionMixin, AsyncAction, View):
 
     def get_success_message(self, value):
         if value['success'] > 0:
-            return _('Your cart timeout was extended.')
+            if value.get('price_changed'):
+                return _('Your cart timeout was extended. Please note that some of the prices in your cart '
+                         'changed.')
+            else:
+                return _('Your cart timeout was extended.')
 
     def post(self, request, *args, **kwargs):
         return self.do(self.request.event.id, get_or_create_cart_id(self.request), translation.get_language(),
@@ -578,7 +582,7 @@ class CartExtendReservation(EventViewMixin, CartActionMixin, AsyncAction, View):
 @method_decorator(iframe_entry_view_wrapper, 'dispatch')
 class CartAdd(EventViewMixin, CartActionMixin, AsyncAction, View):
     task = add_items_to_cart
-    known_errortypes = ['CartError']
+    known_errortypes = ['CartError', 'CartPositionError']
 
     def get_success_message(self, value):
         return _('The products have been successfully added to your cart.')
diff --git a/src/tests/base/test_memberships.py b/src/tests/base/test_memberships.py
index 1b074ccec0..33ce29e684 100644
--- a/src/tests/base/test_memberships.py
+++ b/src/tests/base/test_memberships.py
@@ -745,6 +745,8 @@ def test_use_membership(event, customer, membership, requiring_ticket):
         item=requiring_ticket, price=23, expires=now() + timedelta(days=1), event=event, cart_id="123",
         used_membership=membership
     )
+    q = event.quotas.create(size=None, name="foo")
+    q.items.add(requiring_ticket)
     order = _create_order(event, email='dummy@example.org', positions=[cp1],
                           now_dt=now(),
                           sales_channel=event.organizer.sales_channels.get(identifier="web"),
@@ -767,6 +769,8 @@ def test_use_membership_invalid(event, customer, membership, requiring_ticket):
     membership.date_start -= timedelta(days=100)
     membership.date_end -= timedelta(days=100)
     membership.save()
+    q = event.quotas.create(size=None, name="foo")
+    q.items.add(requiring_ticket)
     cp1 = CartPosition.objects.create(
         item=requiring_ticket, price=23, expires=now() + timedelta(days=1), event=event, cart_id="123",
         used_membership=membership
diff --git a/src/tests/presale/test_cart.py b/src/tests/presale/test_cart.py
index b424227c9c..d02de01908 100644
--- a/src/tests/presale/test_cart.py
+++ b/src/tests/presale/test_cart.py
@@ -1428,6 +1428,27 @@ class CartTest(CartTestMixin, TestCase):
                 self.assertEqual(cp2.expires, now() + self.cart_reservation_time)
                 self.assertEqual(cp2.max_extend, now() + 11 * self.cart_reservation_time)
 
+    def test_expired_cart_extend_price_change_note(self):
+        start_time = datetime.datetime(2024, 1, 1, 10, 00, 00, tzinfo=datetime.timezone.utc)
+        max_extend = start_time + 11 * self.cart_reservation_time
+        with scopes_disabled():
+            cp1 = CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.ticket,
+                price=23, expires=max_extend, max_extend=max_extend
+            )
+            cp1.update_listed_price_and_voucher()
+        self.ticket.default_price = Decimal("25.00")
+        self.ticket.save()
+        with freezegun.freeze_time(max_extend + timedelta(hours=1)):
+            response = self.client.post('/%s/%s/cart/extend' % (self.orga.slug, self.event.slug), {
+            }, follow=True)
+            doc = BeautifulSoup(response.rendered_content, "lxml")
+            self.assertIn('some of the prices in your cart changed', doc.select('.alert-success')[0].text)
+            with scopes_disabled():
+                cp1.refresh_from_db()
+                self.assertEqual(cp1.price, Decimal("25.00"))
+                self.assertEqual(cp1.expires, now() + self.cart_reservation_time)
+
     def test_expired_cart_extend_fails_partially_on_bundled(self):
         start_time = datetime.datetime(2024, 1, 1, 10, 00, 00, tzinfo=datetime.timezone.utc)
         max_extend = start_time + 11 * self.cart_reservation_time
@@ -3408,6 +3429,22 @@ class CartAddonTest(CartTestMixin, TestCase):
         assert cp2.expires > now()
         assert cp2.addon_to_id == cp1.pk
 
+    @classscope(attr='orga')
+    def test_expand_expired_price_change(self):
+        cp1 = CartPosition.objects.create(
+            expires=now() - timedelta(minutes=10), max_extend=now() + 10 * self.cart_reservation_time,
+            item=self.ticket, price=Decimal('23.00'),
+            event=self.event, cart_id=self.session_key
+        )
+        self.ticket.default_price = Decimal("25.00")
+        self.ticket.save()
+        self.cm.extend_expired_positions()
+        self.cm.commit()
+        cp1.refresh_from_db()
+        assert cp1.expires > now()
+        assert cp1.listed_price == Decimal("25.00")
+        assert cp1.price == Decimal("25.00")
+
     @classscope(attr='orga')
     def test_expand_expired_refresh_voucher(self):
         v = Voucher.objects.create(item=self.ticket, value=Decimal('20.00'), event=self.event, price_mode='set',
@@ -4080,6 +4117,8 @@ class CartBundleTest(CartTestMixin, TestCase):
 
     @classscope(attr='orga')
     def test_extend_bundled_and_addon(self):
+        self.trans.require_bundling = False
+        self.trans.save()
         cp = CartPosition.objects.create(
             event=self.event, cart_id=self.session_key, item=self.ticket,
             price=21.5, expires=now() - timedelta(minutes=10), max_extend=now() + 10 * self.cart_reservation_time
diff --git a/src/tests/presale/test_checkout.py b/src/tests/presale/test_checkout.py
index 22d7b4c6d8..f8a6ebd758 100644
--- a/src/tests/presale/test_checkout.py
+++ b/src/tests/presale/test_checkout.py
@@ -2669,7 +2669,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.ticket)
             cr1 = CartPosition.objects.create(
@@ -2839,8 +2839,8 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         with scopes_disabled():
             self.event.has_subevents = True
             self.event.save()
-            se = self.event.subevents.create(name='Foo', date_from=now())
-            se2 = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
+            se2 = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             self.quota_tickets.size = 0
             self.quota_tickets.subevent = se2
             self.quota_tickets.save()
@@ -2880,7 +2880,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.ticket)
             SubEventItem.objects.create(subevent=se, item=self.ticket, price=24)
@@ -2901,7 +2901,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.ticket)
             SubEventItem.objects.create(subevent=se, item=self.ticket, price=24, disabled=True)
@@ -2919,7 +2919,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.workshop2)
             q.variations.add(self.workshop2b)
@@ -2938,7 +2938,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.ticket)
             SubEventItem.objects.create(subevent=se, item=self.ticket, price=24, available_until=now() - timedelta(days=1))
@@ -2956,7 +2956,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             q = se.quotas.create(name="foo", size=None, event=self.event)
             q.items.add(self.workshop2)
             q.variations.add(self.workshop2b)
@@ -3735,8 +3735,8 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.has_subevents = True
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now())
-            se2 = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
+            se2 = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             self.quota_tickets.size = 10
             self.quota_tickets.subevent = se2
             self.quota_tickets.save()
@@ -4165,7 +4165,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         with scopes_disabled():
             self.event.has_subevents = True
             self.event.save()
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
             self.workshopquota.size = 1
             self.workshopquota.subevent = se
             self.workshopquota.save()
@@ -4214,7 +4214,10 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
             self.event.has_subevents = True
             self.event.settings.display_net_prices = True
             self.event.save()
-            se = self.event.subevents.create(name='Foo', date_from=now(), presale_start=now() + datetime.timedelta(days=1))
+            se = self.event.subevents.create(name='Foo', date_from=now(), presale_start=now() + datetime.timedelta(days=1),
+                                             active=True)
+            q = se.quotas.create(name="foo", size=None, event=self.event)
+            q.items.add(self.ticket)
             CartPosition.objects.create(
                 event=self.event, cart_id=self.session_key, item=self.ticket,
                 price=23, expires=now() + timedelta(minutes=10), subevent=se
@@ -4224,7 +4227,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
         doc = BeautifulSoup(response.content.decode(), "lxml")
         self.assertGreaterEqual(len(doc.select(".alert-danger")), 1)
-        assert 'booking period for one of the events in your cart has not yet started.' in response.content.decode()
+        assert 'booking period for this event has not yet started.' in response.content.decode()
         with scopes_disabled():
             assert not CartPosition.objects.filter(cart_id=self.session_key).exists()
 
@@ -4233,7 +4236,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
             self.event.has_subevents = True
             self.event.settings.display_net_prices = True
             self.event.save()
-            se = self.event.subevents.create(name='Foo', date_from=now(), presale_end=now() - datetime.timedelta(days=1))
+            se = self.event.subevents.create(name='Foo', date_from=now(), presale_end=now() - datetime.timedelta(days=1), active=True)
             CartPosition.objects.create(
                 event=self.event, cart_id=self.session_key, item=self.ticket,
                 price=23, expires=now() + timedelta(minutes=10), subevent=se
@@ -4243,7 +4246,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
         doc = BeautifulSoup(response.content.decode(), "lxml")
         self.assertGreaterEqual(len(doc.select(".alert-danger")), 1)
-        assert 'booking period for one of the events in your cart has ended.' in response.content.decode()
+        assert 'The booking period for this event has ended.' in response.content.decode()
         with scopes_disabled():
             assert not CartPosition.objects.filter(cart_id=self.session_key).exists()
 
@@ -4253,7 +4256,9 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
             self.event.settings.display_net_prices = True
             self.event.save()
             self.event.settings.payment_term_last = 'RELDATE/1/23:59:59/date_from/'
-            se = self.event.subevents.create(name='Foo', date_from=now())
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=True)
+            q = se.quotas.create(name="foo", size=None, event=self.event)
+            q.items.add(self.ticket)
             CartPosition.objects.create(
                 event=self.event, cart_id=self.session_key, item=self.ticket,
                 price=23, expires=now() + timedelta(minutes=10), subevent=se
@@ -4263,7 +4268,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
         doc = BeautifulSoup(response.content.decode(), "lxml")
         self.assertGreaterEqual(len(doc.select(".alert-danger")), 1)
-        assert 'booking period for one of the events in your cart has ended.' in response.content.decode()
+        assert 'All payments for this event need to be confirmed already, so no new orders can be created.' in response.content.decode()
         with scopes_disabled():
             assert not CartPosition.objects.filter(cart_id=self.session_key).exists()
 
@@ -4272,7 +4277,10 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         self.event.date_to = now() - datetime.timedelta(days=1)
         self.event.save()
         with scopes_disabled():
-            se = self.event.subevents.create(name='Foo', date_from=now(), presale_end=now() + datetime.timedelta(days=1))
+            se = self.event.subevents.create(name='Foo', date_from=now(), presale_end=now() + datetime.timedelta(days=1),
+                                             active=True)
+            q = se.quotas.create(name="foo", size=None, event=self.event)
+            q.items.add(self.ticket)
             CartPosition.objects.create(
                 event=self.event, cart_id=self.session_key, item=self.ticket,
                 price=23, expires=now() + timedelta(minutes=10), subevent=se
@@ -4283,6 +4291,25 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
         doc = BeautifulSoup(response.content.decode(), "lxml")
         self.assertEqual(len(doc.select(".thank-you")), 1)
 
+    def test_confirm_subevent_disabled(self):
+        with scopes_disabled():
+            self.event.has_subevents = True
+            self.event.settings.display_net_prices = True
+            self.event.save()
+            se = self.event.subevents.create(name='Foo', date_from=now(), active=False)
+            CartPosition.objects.create(
+                event=self.event, cart_id=self.session_key, item=self.ticket,
+                price=23, expires=now() + timedelta(minutes=10), subevent=se
+            )
+
+        self._set_payment()
+        response = self.client.post('/%s/%s/checkout/confirm/' % (self.orga.slug, self.event.slug), follow=True)
+        doc = BeautifulSoup(response.content.decode(), "lxml")
+        self.assertGreaterEqual(len(doc.select(".alert-danger")), 1)
+        assert 'selected event date is not active.' in response.content.decode()
+        with scopes_disabled():
+            assert not CartPosition.objects.filter(cart_id=self.session_key).exists()
+
     def test_before_presale_timemachine(self):
         self._login_with_permission(self.orga)
         self._enable_test_mode()
@@ -4497,6 +4524,8 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
             self.assertEqual(Order.objects.first().locale, 'de')
 
     def test_variation_require_approval(self):
+        self.workshop2.category = None
+        self.workshop2.save()
         self.workshop2a.require_approval = True
         self.workshop2a.save()
         with scopes_disabled():
@@ -4518,6 +4547,7 @@ class CheckoutTestCase(BaseCheckoutTestCase, TimemachineTestMixin, TestCase):
 
     def test_item_with_variations_require_approval(self):
         self.workshop2.require_approval = True
+        self.workshop2.category = None
         self.workshop2.save()
         with scopes_disabled():
             cr1 = CartPosition.objects.create(