diff --git a/doc/api/resources/questions.rst b/doc/api/resources/questions.rst
index d20e11217f..937bc843f6 100644
--- a/doc/api/resources/questions.rst
+++ b/doc/api/resources/questions.rst
@@ -22,6 +22,7 @@ type                                  string                     The expected ty
                                                                  * ``B`` – boolean
                                                                  * ``C`` – choice from a list
                                                                  * ``M`` – multiple choice from a list
+                                                                 * ``F`` – file upload
 required                              boolean                    If ``True``, the question needs to be filled out.
 position                              integer                    An integer, used for sorting
 items                                 list of integers           List of item IDs this question is assigned to.
diff --git a/src/pretix/base/exporters/__init__.py b/src/pretix/base/exporters/__init__.py
index eefda5866d..aa774ae6cf 100644
--- a/src/pretix/base/exporters/__init__.py
+++ b/src/pretix/base/exporters/__init__.py
@@ -1,3 +1,4 @@
+from .answers import *  # noqa
 from .invoices import *  # noqa
 from .json import *  # noqa
 from .mail import *  # noqa
diff --git a/src/pretix/base/exporters/answers.py b/src/pretix/base/exporters/answers.py
new file mode 100644
index 0000000000..1f1f9de014
--- /dev/null
+++ b/src/pretix/base/exporters/answers.py
@@ -0,0 +1,61 @@
+import os
+import tempfile
+from collections import OrderedDict
+from zipfile import ZipFile
+
+from django import forms
+from django.dispatch import receiver
+from django.utils.translation import ugettext_lazy as _
+
+from pretix.base.models import QuestionAnswer
+
+from ..exporter import BaseExporter
+from ..signals import register_data_exporters
+
+
+class AnswerFilesExporter(BaseExporter):
+    identifier = 'answerfiles'
+    verbose_name = _('Answers to file upload questions')
+
+    @property
+    def export_form_fields(self):
+        return OrderedDict(
+            [
+                ('questions',
+                 forms.ModelMultipleChoiceField(
+                     queryset=self.event.questions.filter(type='F'),
+                     label=_('Questions'),
+                     widget=forms.CheckboxSelectMultiple,
+                     required=False
+                 )),
+            ]
+        )
+
+    def render(self, form_data: dict):
+        qs = QuestionAnswer.objects.filter(
+            orderposition__order__event=self.event,
+        ).select_related('orderposition', 'orderposition__order', 'question')
+        if form_data.get('questions'):
+            qs = qs.filter(question__in=form_data['questions'])
+        with tempfile.TemporaryDirectory() as d:
+            with ZipFile(os.path.join(d, 'tmp.zip'), 'w') as zipf:
+                for i in qs:
+                    if i.file:
+                        i.file.open('r')
+                        fname = '{}-{}-{}-q{}-{}'.format(
+                            self.event.slug.upper(),
+                            i.orderposition.order.code,
+                            i.orderposition.positionid,
+                            i.question.pk,
+                            os.path.basename(i.file.name).split('.', 1)[1]
+                        )
+                        zipf.writestr(fname, i.file.read())
+                        i.file.close()
+
+            with open(os.path.join(d, 'tmp.zip'), 'rb') as zipf:
+                return 'answers.zip', 'application/zip', zipf.read()
+
+
+@receiver(register_data_exporters, dispatch_uid="exporter_answers")
+def register_anwers_export(sender, **kwargs):
+    return AnswerFilesExporter
diff --git a/src/pretix/base/migrations/0064_auto_20170703_0912.py b/src/pretix/base/migrations/0064_auto_20170703_0912.py
new file mode 100644
index 0000000000..7a7c3eedfc
--- /dev/null
+++ b/src/pretix/base/migrations/0064_auto_20170703_0912.py
@@ -0,0 +1,27 @@
+# -*- coding: utf-8 -*-
+# Generated by Django 1.11.2 on 2017-07-03 09:12
+from __future__ import unicode_literals
+
+from django.db import migrations, models
+
+import pretix.base.models.orders
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('pretixbase', '0063_auto_20170702_1711'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='questionanswer',
+            name='file',
+            field=models.FileField(blank=True, null=True, upload_to=pretix.base.models.orders.answerfile_name),
+        ),
+        migrations.AlterField(
+            model_name='question',
+            name='type',
+            field=models.CharField(choices=[('N', 'Number'), ('S', 'Text (one line)'), ('T', 'Multiline text'), ('B', 'Yes/No'), ('C', 'Choose one from a list'), ('M', 'Choose multiple from a list'), ('F', 'File upload')], max_length=5, verbose_name='Question type'),
+        ),
+    ]
diff --git a/src/pretix/base/models/base.py b/src/pretix/base/models/base.py
index fc40dcfea8..8f5f576328 100644
--- a/src/pretix/base/models/base.py
+++ b/src/pretix/base/models/base.py
@@ -16,7 +16,7 @@ def cachedfile_name(instance, filename: str) -> str:
 
 class CachedFile(models.Model):
     """
-    A cached file (e.g. pre-generated ticket PDF)
+    An uploaded file, with an optional expiry date.
     """
     id = models.UUIDField(primary_key=True, default=uuid.uuid4)
     expires = models.DateTimeField(null=True, blank=True)
diff --git a/src/pretix/base/models/items.py b/src/pretix/base/models/items.py
index a7593276fb..af82081926 100644
--- a/src/pretix/base/models/items.py
+++ b/src/pretix/base/models/items.py
@@ -446,6 +446,7 @@ class Question(LoggedModel):
     * a multi-line string (``TYPE_TEXT``)
     * a boolean (``TYPE_BOOLEAN``)
     * a multiple choice option (``TYPE_CHOICE`` and ``TYPE_CHOICE_MULTIPLE``)
+    * a file upload (``TYPE_FILE``))
 
     :param event: The event this question belongs to
     :type event: Event
@@ -463,13 +464,15 @@ class Question(LoggedModel):
     TYPE_BOOLEAN = "B"
     TYPE_CHOICE = "C"
     TYPE_CHOICE_MULTIPLE = "M"
+    TYPE_FILE = "F"
     TYPE_CHOICES = (
         (TYPE_NUMBER, _("Number")),
         (TYPE_STRING, _("Text (one line)")),
         (TYPE_TEXT, _("Multiline text")),
         (TYPE_BOOLEAN, _("Yes/No")),
         (TYPE_CHOICE, _("Choose one from a list")),
-        (TYPE_CHOICE_MULTIPLE, _("Choose multiple from a list"))
+        (TYPE_CHOICE_MULTIPLE, _("Choose multiple from a list")),
+        (TYPE_FILE, _("File upload")),
     )
 
     event = models.ForeignKey(
diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index 8a37d3a30f..835010d1db 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -12,7 +12,10 @@ from django.db.models import F, Sum
 from django.db.models.signals import post_delete
 from django.dispatch import receiver
 from django.utils.crypto import get_random_string
+from django.utils.encoding import escape_uri_path
 from django.utils.functional import cached_property
+from django.utils.html import escape
+from django.utils.safestring import mark_safe
 from django.utils.timezone import now
 from django.utils.translation import ugettext_lazy as _
 
@@ -340,6 +343,17 @@ class Order(LoggedModel):
         return True
 
 
+def answerfile_name(instance, filename: str) -> str:
+    secret = get_random_string(length=32, allowed_chars=string.ascii_letters + string.digits)
+    event = (instance.cartposition if instance.cartposition else instance.orderposition.order).event
+    return 'cachedfiles/answers/{org}/{ev}/{secret}.{filename}'.format(
+        org=event.organizer.slug,
+        ev=event.slug,
+        secret=secret,
+        filename=escape_uri_path(filename),
+    )
+
+
 class QuestionAnswer(models.Model):
     """
     The answer to a Question, connected to an OrderPosition or CartPosition.
@@ -370,12 +384,39 @@ class QuestionAnswer(models.Model):
         QuestionOption, related_name='answers', blank=True
     )
     answer = models.TextField()
+    file = models.FileField(
+        null=True, blank=True, upload_to=answerfile_name
+    )
+
+    @property
+    def file_link(self):
+        from pretix.multidomain.urlreverse import eventreverse
+
+        if self.file:
+            if self.orderposition:
+                url = eventreverse(self.orderposition.order.event, 'presale:event.order.download.answer', kwargs={
+                    'order': self.orderposition.order.code,
+                    'secret': self.orderposition.order.secret,
+                    'answer': self.pk,
+                })
+            else:
+                url = eventreverse(self.cartposition.event, 'presale:event.cart.download.answer', kwargs={
+                    'answer': self.pk,
+                })
+
+            return mark_safe("<a href='{}'>{}</a>".format(
+                url,
+                escape(self.file.name.split('.', 1)[-1])
+            ))
+        return ""
 
     def __str__(self):
         if self.question.type == Question.TYPE_BOOLEAN and self.answer == "True":
             return str(_("Yes"))
         elif self.question.type == Question.TYPE_BOOLEAN and self.answer == "False":
             return str(_("No"))
+        elif self.question.type == Question.TYPE_FILE:
+            return str(_("<file>"))
         else:
             return self.answer
 
@@ -684,3 +725,17 @@ def cachedticket_delete(sender, instance, **kwargs):
     if instance.file:
         # Pass false so FileField doesn't save the model.
         instance.file.delete(False)
+
+
+@receiver(post_delete, sender=CachedCombinedTicket)
+def cachedcombinedticket_delete(sender, instance, **kwargs):
+    if instance.file:
+        # Pass false so FileField doesn't save the model.
+        instance.file.delete(False)
+
+
+@receiver(post_delete, sender=QuestionAnswer)
+def answer_delete(sender, instance, **kwargs):
+    if instance.file:
+        # Pass false so FileField doesn't save the model.
+        instance.file.delete(False)
diff --git a/src/pretix/control/templates/pretixcontrol/order/index.html b/src/pretix/control/templates/pretixcontrol/order/index.html
index 3764859e28..3bb1290f67 100644
--- a/src/pretix/control/templates/pretixcontrol/order/index.html
+++ b/src/pretix/control/templates/pretixcontrol/order/index.html
@@ -198,8 +198,17 @@
                                         {% endif %}
                                         {% for q in line.questions %}
                                             <dt>{{ q.question }}</dt>
-                                            <dd>{% if q.answer %}{{ q.answer|linebreaksbr }}{% else %}
-                                                <em>{% trans "not answered" %}</em>{% endif %}</dd>
+                                            <dd>
+                                                {% if q.answer %}
+                                                    {% if q.answer.file %}
+                                                        <span class="fa fa-file"></span> {{ q.answer.file_link }}
+                                                    {% else %}
+                                                        {{ q.answer|linebreaksbr }}
+                                                    {% endif %}
+                                                {% else %}
+                                                    <em>{% trans "not answered" %}</em>
+                                                {% endif %}
+                                            </dd>
                                         {% endfor %}
                                         {% for q in line.additional_fields %}
                                             <dt>{{ q.question }}</dt>
diff --git a/src/pretix/control/views/item.py b/src/pretix/control/views/item.py
index 835a38fde7..adfab590bf 100644
--- a/src/pretix/control/views/item.py
+++ b/src/pretix/control/views/item.py
@@ -414,7 +414,14 @@ class QuestionView(EventPermissionRequiredMixin, QuestionMixin, ChartContainingV
             i = self.request.GET.get("item", "")
             qs = qs.filter(orderposition__item_id__in=(i,))
 
-        if self.object.type in (Question.TYPE_CHOICE, Question.TYPE_CHOICE_MULTIPLE):
+        if self.object.type == Question.TYPE_FILE:
+            qs = [
+                {
+                    'answer': ugettext('File uploaded'),
+                    'count': qs.filter(file__isnull=False).count()
+                }
+            ]
+        elif self.object.type in (Question.TYPE_CHOICE, Question.TYPE_CHOICE_MULTIPLE):
             qs = qs.order_by('options').values('options', 'options__answer')\
                    .annotate(count=Count('id')).order_by('-count')
             for a in qs:
diff --git a/src/pretix/presale/forms/checkout.py b/src/pretix/presale/forms/checkout.py
index 104c75ea02..e49ebb726d 100644
--- a/src/pretix/presale/forms/checkout.py
+++ b/src/pretix/presale/forms/checkout.py
@@ -1,3 +1,4 @@
+import os
 from decimal import Decimal
 from itertools import chain
 
@@ -10,8 +11,9 @@ from django.utils.timezone import now
 from django.utils.translation import ugettext_lazy as _
 
 from pretix.base.models import ItemVariation, Question
-from pretix.base.models.orders import InvoiceAddress
+from pretix.base.models.orders import InvoiceAddress, OrderPosition
 from pretix.base.templatetags.rich_text import rich_text
+from pretix.multidomain.urlreverse import eventreverse
 from pretix.presale.signals import contact_form_fields, question_form_fields
 
 
@@ -73,6 +75,42 @@ class InvoiceAddressForm(forms.ModelForm):
             raise ValidationError(_('You need to provide either a company name or your name.'))
 
 
+class UploadedFileWidget(forms.ClearableFileInput):
+
+    def __init__(self, *args, **kwargs):
+        self.position = kwargs.pop('position')
+        self.event = kwargs.pop('event')
+        self.answer = kwargs.pop('answer')
+        super().__init__(*args, **kwargs)
+
+    class FakeFile:
+        def __init__(self, file, position, event, answer):
+            self.file = file
+            self.position = position
+            self.event = event
+            self.answer = answer
+
+        def __str__(self):
+            return os.path.basename(self.file.name).split('.', 1)[-1]
+
+        @property
+        def url(self):
+            if isinstance(self.position, OrderPosition):
+                return eventreverse(self.event, 'presale:event.order.download.answer', kwargs={
+                    'order': self.position.order.code,
+                    'secret': self.position.order.secret,
+                    'answer': self.answer.pk,
+                })
+            else:
+                return eventreverse(self.event, 'presale:event.cart.download.answer', kwargs={
+                    'answer': self.answer.pk,
+                })
+
+    def format_value(self, value):
+        if self.is_initial(value):
+            return self.FakeFile(value, self.position, self.event, self.answer)
+
+
 class QuestionsForm(forms.Form):
     """
     This form class is responsible for asking order-related questions. This includes
@@ -169,6 +207,12 @@ class QuestionsForm(forms.Form):
                     widget=forms.CheckboxSelectMultiple,
                     initial=initial.options.all() if initial else None,
                 )
+            elif q.type == Question.TYPE_FILE:
+                field = forms.FileField(
+                    label=q.question, required=q.required,
+                    initial=initial.file if initial else None,
+                    widget=UploadedFileWidget(position=pos, event=event, answer=initial)
+                )
             field.question = q
             if answers:
                 # Cache the answer object for later use
diff --git a/src/pretix/presale/templates/pretixpresale/event/checkout_questions.html b/src/pretix/presale/templates/pretixpresale/event/checkout_questions.html
index da509576b9..8116cce309 100644
--- a/src/pretix/presale/templates/pretixpresale/event/checkout_questions.html
+++ b/src/pretix/presale/templates/pretixpresale/event/checkout_questions.html
@@ -5,7 +5,7 @@
 {% block content %}
     <h2>{% trans "Checkout" %}</h2>
     <p>{% trans "Before we continue, we need you to answer some questions." %}</p>
-    <form class="form-horizontal" method="post">
+    <form class="form-horizontal" method="post" enctype="multipart/form-data">
         {% csrf_token %}
         <div class="panel-group" id="questions_group">
             <div class="panel panel-default">
diff --git a/src/pretix/presale/templates/pretixpresale/event/fragment_cart.html b/src/pretix/presale/templates/pretixpresale/event/fragment_cart.html
index 66b37c3cad..b9e0cefba7 100644
--- a/src/pretix/presale/templates/pretixpresale/event/fragment_cart.html
+++ b/src/pretix/presale/templates/pretixpresale/event/fragment_cart.html
@@ -27,7 +27,17 @@
                     {% endif %}
                     {% for q in line.questions %}
                         <dt>{{ q.question }}</dt>
-                        <dd>{% if q.answer %}{{ q.answer|linebreaksbr }}{% else %}<em>{% trans "not answered" %}</em>{% endif %}</dd>
+                        <dd>
+                            {% if q.answer %}
+                                {% if q.answer.file %}
+                                    <span class="fa fa-file"></span> {{ q.answer.file_link }}
+                                {% else %}
+                                    {{ q.answer|linebreaksbr }}
+                                {% endif %}
+                            {% else %}
+                                <em>{% trans "not answered" %}</em>
+                            {% endif %}
+                        </dd>
                     {% endfor %}
                     {% for q in line.additional_answers %}
                         <dt>{{ q.question }}</dt>
diff --git a/src/pretix/presale/templates/pretixpresale/event/order_modify.html b/src/pretix/presale/templates/pretixpresale/event/order_modify.html
index a91f5fb217..5954cac4a5 100644
--- a/src/pretix/presale/templates/pretixpresale/event/order_modify.html
+++ b/src/pretix/presale/templates/pretixpresale/event/order_modify.html
@@ -8,7 +8,7 @@
             Modify order: {{ code }}
         {% endblocktrans %}
     </h2>
-    <form class="form-horizontal" method="post">
+    <form class="form-horizontal" method="post" enctype="multipart/form-data">
         {% csrf_token %}
         <div class="panel-group" id="questions_accordion">
             {% if event.settings.invoice_address_asked %}
diff --git a/src/pretix/presale/urls.py b/src/pretix/presale/urls.py
index 7328719255..758b042a14 100644
--- a/src/pretix/presale/urls.py
+++ b/src/pretix/presale/urls.py
@@ -16,6 +16,9 @@ event_patterns = [
     url(r'^cart/add$', pretix.presale.views.cart.CartAdd.as_view(), name='event.cart.add'),
     url(r'^cart/remove$', pretix.presale.views.cart.CartRemove.as_view(), name='event.cart.remove'),
     url(r'^cart/clear$', pretix.presale.views.cart.CartClear.as_view(), name='event.cart.clear'),
+    url(r'^cart/answer/(?P<answer>[^/]+)/$',
+        pretix.presale.views.cart.AnswerDownload.as_view(),
+        name='event.cart.download.answer'),
     url(r'^waitinglist', pretix.presale.views.waiting.WaitingView.as_view(), name='event.waitinglist'),
     url(r'^checkout/start$', pretix.presale.views.checkout.CheckoutView.as_view(), name='event.checkout.start'),
     url(r'^redeem/?$', pretix.presale.views.cart.RedeemView.as_view(),
@@ -48,6 +51,9 @@ event_patterns = [
     url(r'^order/(?P<order>[^/]+)/(?P<secret>[A-Za-z0-9]+)/pay/change',
         pretix.presale.views.order.OrderPayChangeMethod.as_view(),
         name='event.order.pay.change'),
+    url(r'^order/(?P<order>[^/]+)/(?P<secret>[A-Za-z0-9]+)/answer/(?P<answer>[^/]+)/$',
+        pretix.presale.views.order.AnswerDownload.as_view(),
+        name='event.order.download.answer'),
     url(r'^order/(?P<order>[^/]+)/(?P<secret>[A-Za-z0-9]+)/download/(?P<output>[^/]+)$',
         pretix.presale.views.order.OrderDownload.as_view(),
         name='event.order.download.combined'),
diff --git a/src/pretix/presale/views/cart.py b/src/pretix/presale/views/cart.py
index e095e1be2c..8bce1a33ca 100644
--- a/src/pretix/presale/views/cart.py
+++ b/src/pretix/presale/views/cart.py
@@ -1,14 +1,17 @@
+import mimetypes
+import os
+
 from django.contrib import messages
 from django.db.models import Count, Q
-from django.http import JsonResponse
-from django.shortcuts import redirect
+from django.http import FileResponse, Http404, JsonResponse
+from django.shortcuts import get_object_or_404, redirect
 from django.utils import translation
 from django.utils.timezone import now
 from django.utils.translation import ugettext as _
 from django.views.generic import TemplateView, View
 
 from pretix.base.decimal import round_decimal
-from pretix.base.models import CartPosition, Quota, Voucher
+from pretix.base.models import CartPosition, QuestionAnswer, Quota, Voucher
 from pretix.base.services.cart import (
     CartError, add_items_to_cart, clear_cart, remove_cart_position,
 )
@@ -266,3 +269,23 @@ class RedeemView(EventViewMixin, TemplateView):
             return redirect(eventreverse(request.event, 'presale:event.index'))
 
         return super().dispatch(request, *args, **kwargs)
+
+
+class AnswerDownload(EventViewMixin, View):
+    def get(self, request, *args, **kwargs):
+        answid = kwargs.get('answer')
+        answer = get_object_or_404(
+            QuestionAnswer,
+            cartposition__cart_id=self.request.session.session_key,
+            id=answid
+        )
+        if not answer.file:
+            return Http404()
+
+        ftype, _ = mimetypes.guess_type(answer.file.name)
+        resp = FileResponse(answer.file, content_type=ftype or 'application/binary')
+        resp['Content-Disposition'] = 'attachment; filename="{}-cart-{}"'.format(
+            self.request.event.slug.upper(),
+            os.path.basename(answer.file.name).split('.', 1)[1]
+        )
+        return resp
diff --git a/src/pretix/presale/views/order.py b/src/pretix/presale/views/order.py
index 1de61fb391..e940a5f2d3 100644
--- a/src/pretix/presale/views/order.py
+++ b/src/pretix/presale/views/order.py
@@ -1,15 +1,18 @@
+import mimetypes
+import os
+
 from django.contrib import messages
 from django.db import transaction
 from django.db.models import Sum
 from django.http import FileResponse, Http404, JsonResponse
-from django.shortcuts import redirect, render
+from django.shortcuts import get_object_or_404, redirect, render
 from django.utils.functional import cached_property
 from django.utils.timezone import now
 from django.utils.translation import ugettext_lazy as _
 from django.views.generic import TemplateView, View
 
 from pretix.base.models import CachedTicket, Invoice, Order, OrderPosition
-from pretix.base.models.orders import InvoiceAddress
+from pretix.base.models.orders import InvoiceAddress, QuestionAnswer
 from pretix.base.payment import PaymentException
 from pretix.base.services.invoices import (
     generate_cancellation, generate_invoice, invoice_pdf, invoice_qualified,
@@ -29,13 +32,13 @@ from pretix.presale.views.questions import QuestionsViewMixin
 class OrderDetailMixin:
     @cached_property
     def order(self):
-        try:
-            order = self.request.event.orders.get(code=self.kwargs['order'])
+        order = self.request.event.orders.filter(code=self.kwargs['order']).select_related('event').first()
+        if order:
             if order.secret.lower() == self.kwargs['secret'].lower():
                 return order
             else:
                 return None
-        except Order.DoesNotExist:
+        else:
             # Do a comparison as well to harden timing attacks
             if 'abcdefghijklmnopq'.lower() == self.kwargs['secret'].lower():
                 return None
@@ -89,7 +92,7 @@ class OrderDetails(EventViewMixin, OrderDetailMixin, CartMixin, TemplateView):
         ctx['download_buttons'] = self.download_buttons
         ctx['cart'] = self.get_cart(
             answers=True, downloads=ctx['can_download'],
-            queryset=OrderPosition.objects.filter(order=self.order),
+            queryset=self.order.positions.all(),
             payment_fee=self.order.payment_fee, payment_fee_tax_rate=self.order.payment_fee_tax_rate
         )
         ctx['invoices'] = list(self.order.invoices.all())
@@ -488,6 +491,23 @@ class OrderCancelDo(EventViewMixin, OrderDetailMixin, AsyncAction, View):
         return _('The order has been canceled.')
 
 
+class AnswerDownload(EventViewMixin, OrderDetailMixin, View):
+    def get(self, request, *args, **kwargs):
+        answid = kwargs.get('answer')
+        answer = get_object_or_404(QuestionAnswer, orderposition__order=self.order, id=answid)
+        if not answer.file:
+            return Http404()
+
+        ftype, _ = mimetypes.guess_type(answer.file.name)
+        resp = FileResponse(answer.file, content_type=ftype or 'application/binary')
+        resp['Content-Disposition'] = 'attachment; filename="{}-{}-{}-{}"'.format(
+            self.request.event.slug.upper(), self.order.code,
+            answer.orderposition.positionid,
+            os.path.basename(answer.file.name).split('.', 1)[1]
+        )
+        return resp
+
+
 class OrderDownload(EventViewMixin, OrderDetailMixin, View):
 
     def get_self_url(self):
diff --git a/src/pretix/presale/views/questions.py b/src/pretix/presale/views/questions.py
index fa522313b8..971f4fad85 100644
--- a/src/pretix/presale/views/questions.py
+++ b/src/pretix/presale/views/questions.py
@@ -2,6 +2,7 @@ import json
 from collections import defaultdict
 
 from django import forms
+from django.core.files.uploadedfile import UploadedFile
 from django.utils.functional import cached_property
 
 from pretix.base.models import CartPosition, OrderPosition, QuestionAnswer
@@ -39,7 +40,8 @@ class QuestionsViewMixin:
                                  prefix=cr.id,
                                  cartpos=cartpos,
                                  orderpos=orderpos,
-                                 data=(self.request.POST if self.request.method == 'POST' else None))
+                                 data=(self.request.POST if self.request.method == 'POST' else None),
+                                 files=(self.request.FILES if self.request.method == 'POST' else None))
             form.pos = cartpos or orderpos
             if len(form.fields) > 0:
                 formlist.append(form)
@@ -78,7 +80,9 @@ class QuestionsViewMixin:
                         if hasattr(field, 'answer'):
                             # We already have a cached answer object, so we don't
                             # have to create a new one
-                            if v == '':
+                            if v == '' or v is None or (isinstance(field, forms.FileField) and v is False):
+                                if field.answer.file:
+                                    field.answer.file.delete()
                                 field.answer.delete()
                             else:
                                 self._save_to_answer(field, field.answer, v)
@@ -119,5 +123,9 @@ class QuestionsViewMixin:
                 answer.options.clear()
             answer.options.add(value)
             answer.answer = value.answer
+        elif isinstance(field, forms.FileField):
+            if isinstance(value, UploadedFile):
+                answer.file.save(value.name, value)
+                answer.answer = 'file://' + value.name
         else:
             answer.answer = value
diff --git a/src/tests/presale/test_checkout.py b/src/tests/presale/test_checkout.py
index b2850e4ae1..c42c9b2677 100644
--- a/src/tests/presale/test_checkout.py
+++ b/src/tests/presale/test_checkout.py
@@ -1,9 +1,11 @@
 import datetime
+import os
 from datetime import timedelta
 from decimal import Decimal
 
 from bs4 import BeautifulSoup
 from django.conf import settings
+from django.core.files.uploadedfile import SimpleUploadedFile
 from django.test import TestCase
 from django.utils.timezone import now
 
@@ -110,6 +112,43 @@ class CheckoutTestCase(TestCase):
         self.assertEqual(cr1.answers.filter(question=q2).count(), 1)
         self.assertFalse(cr2.answers.filter(question=q2).exists())
 
+    def test_question_file_upload(self):
+        q1 = Question.objects.create(
+            event=self.event, question='Student ID', type=Question.TYPE_FILE,
+            required=False
+        )
+        self.ticket.questions.add(q1)
+        cr1 = CartPosition.objects.create(
+            event=self.event, cart_id=self.session_key, item=self.ticket,
+            price=23, expires=now() + timedelta(minutes=10)
+        )
+        response = self.client.get('/%s/%s/checkout/questions/' % (self.orga.slug, self.event.slug), follow=True)
+        doc = BeautifulSoup(response.rendered_content, "lxml")
+
+        self.assertEqual(len(doc.select('input[name=%s-question_%s]' % (cr1.id, q1.id))), 1)
+
+        f = SimpleUploadedFile("testfile.txt", b"file_content")
+        response = self.client.post('/%s/%s/checkout/questions/' % (self.orga.slug, self.event.slug), {
+            '%s-question_%s' % (cr1.id, q1.id): f,
+            'email': 'admin@localhost'
+        }, follow=True)
+        self.assertRedirects(response, '/%s/%s/checkout/payment/' % (self.orga.slug, self.event.slug),
+                             target_status_code=200)
+
+        cr1 = CartPosition.objects.get(id=cr1.id)
+        a = cr1.answers.get(question=q1)
+        assert a.file
+        assert a.file.read() == b"file_content"
+        assert os.path.exists(os.path.join(settings.MEDIA_ROOT, a.file.name))
+
+        # Delete
+        self.client.post('/%s/%s/checkout/questions/' % (self.orga.slug, self.event.slug), {
+            '%s-question_%s-clear' % (cr1.id, q1.id): 'on',
+            'email': 'admin@localhost'
+        }, follow=True)
+        assert not cr1.answers.exists()
+        assert not os.path.exists(os.path.join(settings.MEDIA_ROOT, a.file.name))
+
     def test_attendee_email_required(self):
         self.event.settings.set('attendee_emails_asked', True)
         self.event.settings.set('attendee_emails_required', True)