diff --git a/sponsors/models/sponsorship.py b/sponsors/models/sponsorship.py
index 6a12d2f30..7443d4d2c 100644
--- a/sponsors/models/sponsorship.py
+++ b/sponsors/models/sponsorship.py
@@ -383,6 +383,12 @@ def next_status(self):
         }
         return states_map[self.status]
 
+    @property
+    def previous_effective_date(self):
+        if len(self.sponsor.sponsorship_set.all().order_by('-year')) > 1:
+                return self.sponsor.sponsorship_set.all().order_by('-year')[1].start_date
+        return None
+
 
 class SponsorshipBenefit(OrderedModel):
     """
diff --git a/sponsors/pdf.py b/sponsors/pdf.py
index 35585499f..f1b80d911 100644
--- a/sponsors/pdf.py
+++ b/sponsors/pdf.py
@@ -34,6 +34,7 @@ def _contract_context(contract, **context):
         "legal_clauses": _clean_split(contract.legal_clauses.raw),
         "renewal": contract.sponsorship.renewal,
     })
+    context["previous_effective"] = contract.sponsorship.previous_effective_date if contract.sponsorship.previous_effective_date else "UNKNOWN"
     return context
 
 
diff --git a/sponsors/tests/test_pdf.py b/sponsors/tests/test_pdf.py
index fdb6d5835..2116b7c21 100644
--- a/sponsors/tests/test_pdf.py
+++ b/sponsors/tests/test_pdf.py
@@ -29,6 +29,7 @@ def setUp(self):
             "benefits": [],
             "legal_clauses": [],
             "renewal": None,
+            "previous_effective": "UNKNOWN",
         }
         self.template = "sponsors/admin/preview-contract.html"
 
@@ -88,6 +89,7 @@ def test_render_response_with_docx_attachment__renewal(self, MockDocxTemplate):
             "benefits": [],
             "legal_clauses": [],
             "renewal": True,
+            "previous_effective": "UNKNOWN",
         }
         renewal_template = "sponsors/admin/preview-contract.html"
 
diff --git a/sponsors/views_admin.py b/sponsors/views_admin.py
index 8968da1b7..e9a808ccc 100644
--- a/sponsors/views_admin.py
+++ b/sponsors/views_admin.py
@@ -85,7 +85,11 @@ def approve_sponsorship_view(ModelAdmin, request, pk):
             )
             return redirect(redirect_url)
 
-    context = {"sponsorship": sponsorship, "form": form}
+    context = {
+        "sponsorship": sponsorship,
+        "form": form,
+        "previous_effective": sponsorship.previous_effective_date if sponsorship.previous_effective_date else "UNKNOWN",
+    }
     return render(request, "sponsors/admin/approve_application.html", context=context)
 
 
diff --git a/templates/sponsors/admin/approve_application.html b/templates/sponsors/admin/approve_application.html
index 1415f871b..42a5f7382 100644
--- a/templates/sponsors/admin/approve_application.html
+++ b/templates/sponsors/admin/approve_application.html
@@ -2,7 +2,18 @@
 {% extends 'admin/change_form.html' %}
 {% load i18n static sponsors %}
 
-{% block extrastyle %}{{ block.super }}<link rel="stylesheet" type="text/css" href="{% static "admin/css/forms.css" %}">{% endblock %}
+{% block extrastyle %}
+  {{ block.super }}
+  <link rel="stylesheet" type="text/css" href="{% static "admin/css/forms.css" %}">
+  <style>
+    .helptext {
+      font-size: smaller;
+      display: block;
+      padding-top: .5em;
+      color: #999;
+    }
+  </style>
+{% endblock %}
 
 {% block title %}Accept {{ sponsorship }} | python.org{% endblock %}
 
@@ -33,6 +44,14 @@ <h1>Generate Contract for Signing</h1>
 {{ form.media }}
 {{ form.as_p }}
 
+<p>
+  <label for="id_renewal_previous_effective_date">
+    Previous Effective Contract:
+  </label>
+  <span><b>{{ previous_effective }}</b></span>
+  <span class="helptext">The last known contract effective date for this sponsor. This will <i>only</i> impact renewals. If UNKNOWN, you <strong>MUST</strong> update the resulting docx with the correct effective date.</span>
+</p>
+
 <input name="confirm" value="yes" style="display:none">
 <div class="submit-row">
     <input type="submit" value="Approve" class="default">