diff --git a/downloads/templatetags/download_tags.py b/downloads/templatetags/download_tags.py
index 57004ccb4..c72f6d58c 100644
--- a/downloads/templatetags/download_tags.py
+++ b/downloads/templatetags/download_tags.py
@@ -19,3 +19,37 @@ def has_sigstore_materials(files):
 @register.filter
 def has_sbom(files):
     return any(f.sbom_spdx2_file for f in files)
+
+
+@register.filter
+def sort_windows(files):
+    if not files:
+        return files
+
+    # Put Windows files in preferred order
+    files = list(files)
+    windows_files = []
+    other_files = []
+    for preferred in (
+        'Windows installer (64-bit)',
+        'Windows installer (32-bit)',
+        'Windows installer (ARM64)',
+        'Windows help file',
+        'Windows embeddable package (64-bit)',
+        'Windows embeddable package (32-bit)',
+        'Windows embeddable package (ARM64)',
+    ):
+        for file in files:
+            if file.name == preferred:
+                windows_files.append(file)
+                files.remove(file)
+                break
+
+    # Then append any remaining Windows files
+    for file in files:
+        if file.name.startswith('Windows'):
+            windows_files.append(file)
+        else:
+            other_files.append(file)
+
+    return other_files + windows_files
diff --git a/templates/downloads/os_list.html b/templates/downloads/os_list.html
index 67db5233f..1e0177dca 100644
--- a/templates/downloads/os_list.html
+++ b/templates/downloads/os_list.html
@@ -1,6 +1,7 @@
 {% extends "downloads/base.html" %}
 {% load boxes %}
 {% load sitetree %}
+{% load sort_windows from download_tags %}
 
 {% block body_attributes %}class="python download"{% endblock %}
 
@@ -45,7 +46,7 @@ <h2>Stable Releases</h2>
                             {% endif %}
                         {% endif %}
                         <ul>
-                            {% for f in r.files.all %}
+                            {% for f in r.files.all|sort_windows %}
                                 <li>Download <a href="{{ f.url }}">{{ f.name }}</a></li>
                             {% empty %}
                                 <li>No files for this release.</li>
@@ -63,7 +64,7 @@ <h2>Pre-releases</h2>
                     <li>
                         <a href="{{ r.get_absolute_url }}">{{ r.name }} - {{ r.release_date|date }}</a>
                         <ul>
-                            {% for f in r.files.all %}
+                            {% for f in r.files.all|sort_windows %}
                                 <li>Download <a href="{{ f.url }}">{{ f.name }}</a></li>
                             {% empty %}
                                 <li>No files for this release.</li>
diff --git a/templates/downloads/release_detail.html b/templates/downloads/release_detail.html
index 730b9b273..c1341936b 100644
--- a/templates/downloads/release_detail.html
+++ b/templates/downloads/release_detail.html
@@ -3,6 +3,7 @@
 {% load sitetree %}
 {% load has_sigstore_materials from download_tags %}
 {% load has_sbom from download_tags %}
+{% load sort_windows from download_tags %}
 
 {% block body_attributes %}class="python downloads"{% endblock %}
 
@@ -60,7 +61,7 @@ <h1 class="page-title">Files</h1>
             </tr>
           </thead>
           <tbody>
-            {% for f in release_files %}
+            {% for f in release_files|sort_windows %}
               <tr>
                 <td><a href="{{ f.url }}">{{ f.name }}</a></td>
                 <td>{{ f.os.name }}</td>