diff --git a/app/navigation.py b/app/navigation.py
index c7eafb68b..f0d30ffbd 100644
--- a/app/navigation.py
+++ b/app/navigation.py
@@ -633,9 +633,12 @@ class CaseworkNavigation(Navigation):
             'view_notifications',
             'view_notification',
         },
-        'uploaded-files': {
+        'uploads': {
             'view_jobs',
             'view_job',
+            'upload_letter',
+            'uploaded_letter_preview',
+            'uploads',
         },
     }
 
@@ -868,9 +871,6 @@ class CaseworkNavigation(Navigation):
         'two_factor_email_sent',
         'update_email_branding',
         'update_letter_branding',
-        'upload_letter',
-        'uploaded_letter_preview',
-        'uploads',
         'usage',
         'usage_for_all_services',
         'user_information',
diff --git a/app/templates/main_nav.html b/app/templates/main_nav.html
index b81503ad8..884a78441 100644
--- a/app/templates/main_nav.html
+++ b/app/templates/main_nav.html
@@ -8,15 +8,16 @@
   {% endif %}
   {% if current_user.has_permissions() %}
     <li><a href="{{ url_for('.choose_template', service_id=current_service.id) }}" {{ main_navigation.is_selected('templates') }}>Templates</a></li>
-    {% if not current_user.has_permissions('view_activity') %}
+    {% if current_user.has_permissions('view_activity') %}
+      {% if current_service.can_upload_letters %}
+        <li><a href="{{ url_for('main.uploads', service_id=current_service.id) }}" {{ main_navigation.is_selected('uploads') }}>Uploads</a></li>
+      {% endif %}
+    {% else %}
       <li><a href="{{ url_for('.view_notifications', service_id=current_service.id, status='sending,delivered,failed') }}" {{ casework_navigation.is_selected('sent-messages') }}>Sent messages</a></li>
-      {% if current_service.has_jobs %}
-        <li><a href="{{ url_for('.view_jobs', service_id=current_service.id) }}" {{ casework_navigation.is_selected('uploaded-files') }}>Uploads</a></li>
+      {% if current_service.has_jobs or current_service.can_upload_letters %}
+        <li><a href="{{ url_for('main.uploads', service_id=current_service.id) }}" {{ casework_navigation.is_selected('uploads') }}>Uploads</a></li>
       {% endif %}
     {% endif %}
-  {% endif %}
-  {% if current_service.can_upload_letters %}
-    <li><a href="{{ url_for('main.uploads', service_id=current_service.id) }}" {{ main_navigation.is_selected('uploads') }}>Uploads</a></li>
   {% endif %}
     <li><a href="{{ url_for('.manage_users', service_id=current_service.id) }}" {{ main_navigation.is_selected('team-members') }}>Team members</a></li>
   {% if current_user.has_permissions('manage_service', allow_org_user=True) %}