diff --git a/sponsors/admin.py b/sponsors/admin.py
index 243d20d7f..aba5a2081 100644
--- a/sponsors/admin.py
+++ b/sponsors/admin.py
@@ -48,8 +48,8 @@ class SponsorshipProgramAdmin(OrderedModelAdmin):
 
 
 class MultiPartForceForm(ModelForm):
-     def is_multipart(self):
-         return True
+    def is_multipart(self):
+        return True
 
 
 class BenefitFeatureConfigurationInline(StackedPolymorphicInline):
diff --git a/sponsors/forms.py b/sponsors/forms.py
index ee845a0a7..e436fa9a3 100644
--- a/sponsors/forms.py
+++ b/sponsors/forms.py
@@ -1,3 +1,4 @@
+import datetime
 from itertools import chain
 from django import forms
 from django.conf import settings
@@ -5,6 +6,7 @@
 from django.db.models import Q
 from django.utils import timezone
 from django.utils.functional import cached_property
+from django.utils.safestring import mark_safe
 from django.utils.text import slugify
 from django.utils.translation import gettext_lazy as _
 from django_countries.fields import CountryField
@@ -614,11 +616,24 @@ def __init__(self, *args, **kwargs):
             self.required_assets = self.required_assets.filter(pk__in=required_assets_ids)
 
         fields = {}
-        for required_asset in self.required_assets:
+        ordered_assets = sorted(
+            self.required_assets,
+            key=lambda x: (-int(bool(x.value)), x.due_date if x.due_date else datetime.date.min),
+            reverse=True,
+        )
+
+        for required_asset in ordered_assets:
             value = required_asset.value
             f_name = self._get_field_name(required_asset)
             required = bool(value)
-            fields[f_name] = required_asset.as_form_field(required=required, initial=value)
+            field = required_asset.as_form_field(required=required, initial=value)
+
+            if required_asset.due_date and not bool(value):
+                field.label = mark_safe(f"{field.label} <b>(Required by {required_asset.due_date})</b>")
+            if bool(value):
+                field.label = mark_safe(f"{field.label} <small>(Fulfilled, thank you!)</small>")
+
+            fields[f_name] = field
 
         self.fields.update(fields)
 
diff --git a/sponsors/management/commands/check_sponsorship_assets_due_date.py b/sponsors/management/commands/check_sponsorship_assets_due_date.py
new file mode 100644
index 000000000..d81f212f8
--- /dev/null
+++ b/sponsors/management/commands/check_sponsorship_assets_due_date.py
@@ -0,0 +1,64 @@
+from datetime import timedelta
+
+from django.core.management import BaseCommand
+from django.db.models import Subquery
+from django.utils import timezone
+
+from sponsors.models import Sponsorship, Contract, BenefitFeature
+from sponsors.notifications import AssetCloseToDueDateNotificationToSponsors
+
+
+class Command(BaseCommand):
+    """
+    This command will query for the sponsorships which have any required asset
+    with a due date expiring within the certain amount of days
+    """
+    help = "Send notifications to sponsorship with pending required assets"
+
+    def add_arguments(self, parser):
+        help = "Num of days to be used as interval up to target date"
+        parser.add_argument("num_days", nargs="?", default="7", help=help)
+        parser.add_argument("--no-input", action="store_true", help="Tells Django to NOT prompt the user for input of any kind.")
+
+    def handle(self, **options):
+        num_days = options["num_days"]
+        ask_input = not options["no_input"]
+        target_date = (timezone.now() + timedelta(days=int(num_days))).date()
+
+        req_assets = BenefitFeature.objects.required_assets()
+
+        sponsorship_ids = Subquery(req_assets.values_list("sponsor_benefit__sponsorship_id").distinct())
+        sponsorships = Sponsorship.objects.filter(id__in=sponsorship_ids)
+
+        sponsorships_to_notify = []
+        for sponsorship in sponsorships:
+            to_notify = any([
+                asset.due_date == target_date
+                for asset in req_assets.from_sponsorship(sponsorship)
+                if asset.due_date
+            ])
+            if to_notify:
+                sponsorships_to_notify.append(sponsorship)
+
+        if not sponsorships_to_notify:
+            print("No sponsorship with required assets with due date close to expiration.")
+            return
+
+        user_input = ""
+        while user_input != "Y" and ask_input:
+            msg = f"Contacts from {len(sponsorships_to_notify)} with pending assets with expiring due date will get " \
+                  f"notified. "
+            msg += "Do you want to proceed? [Y/n]: "
+            user_input = input(msg).strip().upper()
+            if user_input == "N":
+                print("Finishing execution.")
+                return
+            elif user_input != "Y":
+                print("Invalid option...")
+
+        notification = AssetCloseToDueDateNotificationToSponsors()
+        for sponsorship in sponsorships_to_notify:
+            kwargs = {"sponsorship": sponsorship, "due_date": target_date}
+            notification.notify(**kwargs)
+
+        print("Notifications sent!")
diff --git a/sponsors/migrations/0071_auto_20220113_1843.py b/sponsors/migrations/0071_auto_20220113_1843.py
new file mode 100644
index 000000000..7c66e5ba5
--- /dev/null
+++ b/sponsors/migrations/0071_auto_20220113_1843.py
@@ -0,0 +1,33 @@
+# Generated by Django 2.2.24 on 2022-01-13 18:43
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('sponsors', '0070_auto_20220111_2055'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='requiredimgasset',
+            name='due_date',
+            field=models.DateField(blank=True, default=None, null=True),
+        ),
+        migrations.AddField(
+            model_name='requiredimgassetconfiguration',
+            name='due_date',
+            field=models.DateField(blank=True, default=None, null=True),
+        ),
+        migrations.AddField(
+            model_name='requiredtextasset',
+            name='due_date',
+            field=models.DateField(blank=True, default=None, null=True),
+        ),
+        migrations.AddField(
+            model_name='requiredtextassetconfiguration',
+            name='due_date',
+            field=models.DateField(blank=True, default=None, null=True),
+        ),
+    ]
diff --git a/sponsors/migrations/0072_auto_20220125_2005.py b/sponsors/migrations/0072_auto_20220125_2005.py
new file mode 100644
index 000000000..86247bc08
--- /dev/null
+++ b/sponsors/migrations/0072_auto_20220125_2005.py
@@ -0,0 +1,23 @@
+# Generated by Django 2.2.24 on 2022-01-25 20:05
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('sponsors', '0071_auto_20220113_1843'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='requiredtextasset',
+            name='max_length',
+            field=models.IntegerField(blank=True, default=None, help_text='Limit to length of the input, empty means unlimited', null=True),
+        ),
+        migrations.AddField(
+            model_name='requiredtextassetconfiguration',
+            name='max_length',
+            field=models.IntegerField(blank=True, default=None, help_text='Limit to length of the input, empty means unlimited', null=True),
+        ),
+    ]
diff --git a/sponsors/models/benefits.py b/sponsors/models/benefits.py
index c99b1e317..a6eadce6a 100644
--- a/sponsors/models/benefits.py
+++ b/sponsors/models/benefits.py
@@ -88,6 +88,8 @@ class Meta:
 
 
 class BaseRequiredAsset(BaseAsset):
+    due_date = models.DateField(default=None, null=True, blank=True)
+
     class Meta:
         abstract = True
 
@@ -161,6 +163,12 @@ class BaseRequiredTextAsset(BaseRequiredAsset):
         default="",
         blank=True
     )
+    max_length = models.IntegerField(
+        default=None,
+        help_text="Limit to length of the input, empty means unlimited",
+        null=True,
+        blank=True,
+    )
 
     class Meta(BaseRequiredAsset.Meta):
         abstract = True
@@ -532,7 +540,11 @@ def as_form_field(self, **kwargs):
         help_text = kwargs.pop("help_text", self.help_text)
         label = kwargs.pop("label", self.label)
         required = kwargs.pop("required", False)
-        return forms.CharField(required=required, help_text=help_text, label=label, widget=forms.TextInput, **kwargs)
+        max_length = self.max_length
+        widget = forms.TextInput
+        if max_length is None or max_length > 256:
+            widget = forms.Textarea
+        return forms.CharField(required=required, help_text=help_text, label=label, widget=widget, **kwargs)
 
 
 class ProvidedTextAsset(ProvidedAssetMixin, BaseProvidedTextAsset, BenefitFeature):
diff --git a/sponsors/models/sponsors.py b/sponsors/models/sponsors.py
index 7475281a7..fad84d7dc 100644
--- a/sponsors/models/sponsors.py
+++ b/sponsors/models/sponsors.py
@@ -273,7 +273,6 @@ def reset_attributes(self, benefit):
 
         self.save()
 
-
     def delete(self):
         self.features.all().delete()
         super().delete()
diff --git a/sponsors/notifications.py b/sponsors/notifications.py
index 66c980550..e2cccfff4 100644
--- a/sponsors/notifications.py
+++ b/sponsors/notifications.py
@@ -216,3 +216,17 @@ class RefreshSponsorshipsCache:
     def notify(self, *args, **kwargs):
         # clean up cached used by "sponsors/partials/sponsors-list.html"
         cache.delete("CACHED_SPONSORS_LIST")
+
+
+class AssetCloseToDueDateNotificationToSponsors(BaseEmailSponsorshipNotification):
+    subject_template = "sponsors/email/sponsor_expiring_assets_subject.txt"
+    message_template = "sponsors/email/sponsor_expiring_assets.txt"
+    email_context_keys = ["sponsorship", "required_assets", "due_date"]
+
+    def get_recipient_list(self, context):
+        return context["sponsorship"].verified_emails
+
+    def get_email_context(self, **kwargs):
+        context = super().get_email_context(**kwargs)
+        context["required_assets"] = BenefitFeature.objects.from_sponsorship(context["sponsorship"]).required_assets()
+        return context
diff --git a/sponsors/tests/test_models.py b/sponsors/tests/test_models.py
index 0822a9efa..507bc1b57 100644
--- a/sponsors/tests/test_models.py
+++ b/sponsors/tests/test_models.py
@@ -976,6 +976,15 @@ def test_build_form_field_from_input(self):
         text_asset = baker.make(RequiredTextAsset, _fill_optional=True)
         field = text_asset.as_form_field()
         self.assertIsInstance(field, forms.CharField)
+        self.assertIsInstance(field.widget, forms.Textarea)
+        self.assertFalse(field.required)
+        self.assertEqual(text_asset.help_text, field.help_text)
+        self.assertEqual(text_asset.label, field.label)
+
+    def test_build_form_field_from_input_with_max_length(self):
+        text_asset = baker.make(RequiredTextAsset, _fill_optional=True, max_length=256)
+        field = text_asset.as_form_field()
+        self.assertIsInstance(field, forms.CharField)
         self.assertIsInstance(field.widget, forms.TextInput)
         self.assertFalse(field.required)
         self.assertEqual(text_asset.help_text, field.help_text)
diff --git a/sponsors/tests/test_notifications.py b/sponsors/tests/test_notifications.py
index 27edc2501..b3813eddf 100644
--- a/sponsors/tests/test_notifications.py
+++ b/sponsors/tests/test_notifications.py
@@ -1,3 +1,4 @@
+from datetime import date
 from unittest.mock import Mock
 
 from model_bakery import baker
@@ -428,3 +429,60 @@ def test_create_log_entry(self):
         self.assertEqual(str(self.sponsorship), log_entry.object_repr)
         self.assertEqual(log_entry.action_flag, CHANGE)
         self.assertEqual(log_entry.change_message, "Notification 'Foo' was sent to contacts: administrative")
+
+
+class AssetCloseToDueDateNotificationToSponsorsTestCase(TestCase):
+    def setUp(self):
+        self.notification = notifications.AssetCloseToDueDateNotificationToSponsors()
+        self.user = baker.make(settings.AUTH_USER_MODEL, email="foo@foo.com")
+        self.verified_email = baker.make(EmailAddress, verified=True)
+        self.unverified_email = baker.make(EmailAddress, verified=False)
+        self.sponsor_contacts = [
+            baker.make(
+                "sponsors.SponsorContact",
+                email="foo@example.com",
+                primary=True,
+                sponsor__name="foo",
+            ),
+            baker.make("sponsors.SponsorContact", email=self.verified_email.email),
+            baker.make("sponsors.SponsorContact", email=self.unverified_email.email),
+        ]
+        self.sponsor = baker.make("sponsors.Sponsor", contacts=self.sponsor_contacts)
+        self.sponsorship = baker.make(
+            "sponsors.Sponsorship", sponsor=self.sponsor, submited_by=self.user
+        )
+        self.subject_template = "sponsors/email/sponsor_expiring_assets_subject.txt"
+        self.content_template = "sponsors/email/sponsor_expiring_assets.txt"
+
+    def test_send_email_using_correct_templates(self):
+        context = {"sponsorship": self.sponsorship}
+        expected_subject = render_to_string(self.subject_template, context).strip()
+        expected_content = render_to_string(self.content_template, context).strip()
+
+        self.notification.notify(sponsorship=self.sponsorship)
+        self.assertTrue(mail.outbox)
+
+        email = mail.outbox[0]
+        self.assertEqual(expected_subject, email.subject)
+        self.assertEqual(expected_content, email.body)
+        self.assertEqual(settings.SPONSORSHIP_NOTIFICATION_FROM_EMAIL, email.from_email)
+        self.assertCountEqual([self.user.email, self.verified_email.email], email.to)
+
+    def test_send_email_to_correct_recipients(self):
+        context = {"user": self.user, "sponsorship": self.sponsorship}
+        expected_contacts = ["foo@foo.com", self.verified_email.email]
+        self.assertCountEqual(
+            expected_contacts, self.notification.get_recipient_list(context)
+        )
+
+    def test_list_required_assets_in_email_context(self):
+        cfg = baker.make(RequiredTextAssetConfiguration, internal_name='input')
+        benefit = baker.make(SponsorBenefit, sponsorship=self.sponsorship)
+        asset = cfg.create_benefit_feature(benefit)
+        base_context = {"sponsorship": self.sponsorship, "due_date": date.today()}
+        context = self.notification.get_email_context(**base_context)
+        self.assertEqual(3, len(context))
+        self.assertEqual(self.sponsorship, context["sponsorship"])
+        self.assertEqual(1, len(context["required_assets"]))
+        self.assertEqual(date.today(), context["due_date"])
+        self.assertIn(asset, context["required_assets"])
diff --git a/templates/sponsors/email/sponsor_expiring_assets.txt b/templates/sponsors/email/sponsor_expiring_assets.txt
new file mode 100644
index 000000000..4c86d903c
--- /dev/null
+++ b/templates/sponsors/email/sponsor_expiring_assets.txt
@@ -0,0 +1,10 @@
+Hello {{ sponsorship.sponsor.name }} team!,
+
+Your sponsorship requires one or more assets by {{ due_date|date }} in order for us to fulfill your benefits:
+
+You can submit your assets via the following link:
+
+https://python.org{% url "users:sponsorship_application_detail" sponsorship.pk %}
+
+Thanks,
+Python Software Foundation
diff --git a/templates/sponsors/email/sponsor_expiring_assets_subject.txt b/templates/sponsors/email/sponsor_expiring_assets_subject.txt
new file mode 100644
index 000000000..82d3a2c86
--- /dev/null
+++ b/templates/sponsors/email/sponsor_expiring_assets_subject.txt
@@ -0,0 +1 @@
+The PSF needs more information in order fulill some of your Sponsorhip benefits!
diff --git a/templates/users/sponsorship_detail.html b/templates/users/sponsorship_detail.html
index 6c9bceb13..447b4245c 100644
--- a/templates/users/sponsorship_detail.html
+++ b/templates/users/sponsorship_detail.html
@@ -93,14 +93,14 @@ <h3>Application Data</h3>
         {% if required_assets or fulfilled_assets %}
         <div id="assets-info" class="card-info">
           <h3>Required Assets</h3>
-          <p><small>You've selected benefits which requires extra assets (logos, slides etc).</small></p>
+          <p><small>You've selected benefits which requires extra assets (logos, slides etc) in order to be fulfilled.</small></p>
           <br/>
           <ul>
             {% for asset in required_assets %}
-              <li><b>{{ asset.label }}</b>: pending. <a href="{{ asset.user_edit_url }}">Add asset</a>.</li>
+              <li><b>{{ asset.label }}</b><br>Incomplete{% if asset.due_date %} <b>Required by {{ asset.due_date }}</b>{% endif %}: <a href="{{ asset.user_edit_url }}">Add asset</a>.</li>
             {% endfor %}
           {% for asset in fulfilled_assets %}
-            <li><b>{{ asset.label }}</b>: fulfilled. <a href="{{ asset.user_edit_url }}">Edit asset</a>.</li>
+            <li><b>{{ asset.label }}</b><br>Fulfilled: <a href="{{ asset.user_edit_url }}">Edit asset</a>.</li>
           {% endfor %}
           </ul>
           <br/>