diff --git a/downloads/views.py b/downloads/views.py
index 21e66cd55..57196d622 100644
--- a/downloads/views.py
+++ b/downloads/views.py
@@ -2,7 +2,7 @@
 
 from datetime import datetime
 
-from django.db.models import Prefetch
+from django.db.models import Case, IntegerField, Prefetch, When
 from django.urls import reverse
 from django.utils import timezone
 from django.views.generic import DetailView, TemplateView, ListView, RedirectView
@@ -157,6 +157,20 @@ def get_object(self):
     def get_context_data(self, **kwargs):
         context = super().get_context_data(**kwargs)
 
+        # Add featured files (files with download_button=True)
+        # Order: macOS first, Windows second, Source last
+        context['featured_files'] = self.object.files.filter(
+            download_button=True
+        ).annotate(
+            os_order=Case(
+                When(os__slug='macos', then=1),
+                When(os__slug='windows', then=2),
+                When(os__slug='source', then=3),
+                default=4,
+                output_field=IntegerField(),
+            )
+        ).order_by('os_order')
+
         # Manually add release files for better ordering
         context['release_files'] = []
 
diff --git a/static/sass/style.css b/static/sass/style.css
index 09c849482..b66cc9de4 100644
--- a/static/sass/style.css
+++ b/static/sass/style.css
@@ -2113,6 +2113,50 @@ table tfoot {
 .download-widget p:last-child a {
   white-space: nowrap; }
 
+.featured-downloads-list {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 1.5em;
+  justify-content: center;
+  margin-bottom: 2em; }
+
+.featured-download-box {
+  background-color: #f2f4f6;
+  border: 1px solid #caccce;
+  border-radius: 5px;
+  display: flex;
+  flex: 1 1 300px;
+  flex-direction: column;
+  min-width: 250px;
+  max-width: 400px;
+  padding: 1.25em; }
+  .featured-download-box h3 {
+    margin-top: 0; }
+  .featured-download-box .button {
+    background-color: #ffd343;
+    *zoom: 1;
+    filter: progid:DXImageTransform.Microsoft.gradient(gradientType=0, startColorstr='#FFFFDF76', endColorstr='#FFFFD343');
+    background-image: -webkit-gradient(linear, 50% 0%, 50% 100%, color-stop(10%, #ffdf76), color-stop(90%, #ffd343));
+    background-image: -webkit-linear-gradient(#ffdf76 10%, #ffd343 90%);
+    background-image: -moz-linear-gradient(#ffdf76 10%, #ffd343 90%);
+    background-image: -o-linear-gradient(#ffdf76 10%, #ffd343 90%);
+    background-image: linear-gradient(#ffdf76 10%, #ffd343 90%);
+    border: 1px solid #dca900;
+    white-space: normal; }
+    .featured-download-box .button:hover, .featured-download-box .button:active {
+      background-color: inherit;
+      background-color: #ffd343;
+      *zoom: 1;
+      filter: progid:DXImageTransform.Microsoft.gradient(gradientType=0, startColorstr='#FFFFEBA9', endColorstr='#FFFFD343');
+      background-image: -webkit-gradient(linear, 50% 0%, 50% 100%, color-stop(10%, #ffeba9), color-stop(90%, #ffd343));
+      background-image: -webkit-linear-gradient(#ffeba9 10%, #ffd343 90%);
+      background-image: -moz-linear-gradient(#ffeba9 10%, #ffd343 90%);
+      background-image: -o-linear-gradient(#ffeba9 10%, #ffd343 90%);
+      background-image: linear-gradient(#ffeba9 10%, #ffd343 90%); }
+  .featured-download-box .download-buttons {
+    margin-bottom: 0;
+    text-align: center; }
+
 .time-posted {
   display: block;
   font-size: 0.875em;
diff --git a/static/sass/style.scss b/static/sass/style.scss
index cb78d9a4d..174a73374 100644
--- a/static/sass/style.scss
+++ b/static/sass/style.scss
@@ -1098,6 +1098,46 @@ $colors: $blue, $psf, $yellow, $green, $purple, $red;
     p:last-child a { white-space: nowrap; }
 }
 
+.featured-downloads-list {
+    display: flex;
+    flex-wrap: wrap;
+    gap: 1.5em;
+    justify-content: center;
+    margin-bottom: 2em;
+}
+
+.featured-download-box {
+    background-color: $grey-lighterest;
+    border: 1px solid $default-border-color;
+    border-radius: 5px;
+    display: flex;
+    flex: 1 1 300px;
+    flex-direction: column;
+    min-width: 250px;
+    max-width: 400px;
+    padding: 1.25em;
+
+    h3 {
+        margin-top: 0;
+    }
+
+    .button {
+        @include vertical-gradient( lighten($yellow, 10%), $yellow );
+        border: 1px solid darken($yellow, 20%);
+        white-space: normal;
+
+        &:hover, &:active {
+            background-color: inherit;
+            @include vertical-gradient( lighten($yellow, 20%), $yellow );
+        }
+    }
+
+    .download-buttons {
+        margin-bottom: 0;
+        text-align: center;
+    }
+}
+
 .documentation-widget { }
 
 .jobs-widget { }
diff --git a/templates/downloads/release_detail.html b/templates/downloads/release_detail.html
index db49d974e..5959dfe30 100644
--- a/templates/downloads/release_detail.html
+++ b/templates/downloads/release_detail.html
@@ -41,9 +41,26 @@ <h1 class="page-title">{{ release.name }}</h1>
         {% endif %}
 
         <header class="article-header">
-            <h1 class="page-title">Files</h1>
+            <h2 class="page-title">Files</h2>
         </header>
 
+        {% if featured_files %}
+        <div class="featured-downloads-list">
+            {% for f in featured_files %}
+            <div class="featured-download-box">
+                <h3>{{ f.os.name }}</h3>
+                <p class="download-buttons">
+                    {% if f.os.slug == 'windows' and latest_pymanager and release.is_version_at_least_3_5 %}
+                    <a class="button" href="https://www.python.org/downloads/latest/pymanager/">Download Python install manager</a>
+                    {% else %}
+                    <a class="button" href="{{ f.url }}">Download {{ f.name }}</a>
+                    {% endif %}
+                </p>
+            </div>
+            {% endfor %}
+        </div>
+        {% endif %}
+
         <table>
           <thead>
             <tr>