diff --git a/src/pretix/control/views/checkin.py b/src/pretix/control/views/checkin.py
index db0f836239..e6a20d627c 100644
--- a/src/pretix/control/views/checkin.py
+++ b/src/pretix/control/views/checkin.py
@@ -141,7 +141,9 @@ class CheckInListShow(EventPermissionRequiredMixin, PaginationMixin, ListView):
             for op in positions:
                 if op.order.status == Order.STATUS_PAID or (self.list.include_pending and op.order.status == Order.STATUS_PENDING):
                     t = Checkin.TYPE_EXIT if request.POST.get('checkout') == 'true' else Checkin.TYPE_ENTRY
-                    if self.list.allow_multiple_entries or t != Checkin.TYPE_ENTRY:
+
+                    lci = op.checkins.filter(list=self.list).first()
+                    if self.list.allow_multiple_entries or t != Checkin.TYPE_ENTRY or (lci and lci.type != Checkin.TYPE_ENTRY):
                         ci = Checkin.objects.create(position=op, list=self.list, datetime=now(), type=t)
                         created = True
                     else: