diff --git a/app/assets/stylesheets/companion_window.scss b/app/assets/stylesheets/companion_window.scss
index afe2bc0bd..55a5ee422 100644
--- a/app/assets/stylesheets/companion_window.scss
+++ b/app/assets/stylesheets/companion_window.scss
@@ -130,8 +130,10 @@
 
       ul {
         list-style: none;
+        padding: 0px;
 
         li {
+          margin-left: var(--drawer-content-padding);
           margin-bottom: 1rem;
           border-bottom: 1px solid lightgray;
         }
diff --git a/app/components/embed/companion_windows_component.html.erb b/app/components/embed/companion_windows_component.html.erb
index 2b4219acf..520afb7ee 100644
--- a/app/components/embed/companion_windows_component.html.erb
+++ b/app/components/embed/companion_windows_component.html.erb
@@ -90,7 +90,7 @@
           Files
         </h3>
         <ul>
-          <%= render Embed::Download::FileListItemComponent.with_collection(downloadable_files) %>
+          <%= render Embed::Download::FileListItemComponent.with_collection(downloadable_files, show_headers: show_headers?) %>
         </ul>
       <% else %>
         <p>No downloads available</p>
diff --git a/app/components/embed/companion_windows_component.rb b/app/components/embed/companion_windows_component.rb
index 4aa9b16f1..df898e1e5 100644
--- a/app/components/embed/companion_windows_component.rb
+++ b/app/components/embed/companion_windows_component.rb
@@ -38,5 +38,12 @@ def requested_by_chromium?
 
       false
     end
+
+    # We use this in the download FileListComponent to determine if we need to group files.
+    # For example, if a media file has a caption or transcript
+    # we will want to group the caption with the media file.
+    def show_headers?
+      downloadable_files.any? { |file| file.caption? || file.transcript? }
+    end
   end
 end
diff --git a/app/components/embed/download/file_list_item_component.html.erb b/app/components/embed/download/file_list_item_component.html.erb
index 277695e58..6bf2383b3 100644
--- a/app/components/embed/download/file_list_item_component.html.erb
+++ b/app/components/embed/download/file_list_item_component.html.erb
@@ -1,3 +1,6 @@
+<% if show_headers && !file.caption? && !file.transcript? %>
+    <h4><%= download_label %></h4>
+<% end %>
 <li>
   <a href='<%= url %>' target='_blank' rel='noopener noreferrer' download>
     Download <%= download_label %>
diff --git a/app/components/embed/download/file_list_item_component.rb b/app/components/embed/download/file_list_item_component.rb
index 57aecdc18..a2657299a 100644
--- a/app/components/embed/download/file_list_item_component.rb
+++ b/app/components/embed/download/file_list_item_component.rb
@@ -4,11 +4,12 @@ module Embed
   module Download
     class FileListItemComponent < ViewComponent::Base
       include Embed::PrettyFilesize
-      def initialize(file_list_item:, prefer_filename: false)
+      def initialize(file_list_item:, prefer_filename: false, show_headers: false)
         @file = file_list_item
         @prefer_filename = prefer_filename
+        @show_headers = show_headers
       end
-      attr_reader :file
+      attr_reader :file, :show_headers
 
       def file_size
         "(#{pretty_filesize(file.size)})" if file.size