diff --git a/app/controllers/action_text/markdown/uploads_controller.rb b/app/controllers/action_text/markdown/uploads_controller.rb
index f7d4292a..3da17c36 100644
--- a/app/controllers/action_text/markdown/uploads_controller.rb
+++ b/app/controllers/action_text/markdown/uploads_controller.rb
@@ -51,8 +51,10 @@ def set_attachment
 
     # An unpublished book's uploads are as private as the book itself. Serving them to
     # anyone holding the URL made this a way to read them without an access row, and
-    # caching them publicly for a year put them in shared caches besides.
+    # caching them publicly for a year put them in shared caches besides. An attachment
+    # whose owning book can't be resolved has no book to authorize against, so fail
+    # closed rather than letting the nil short-circuit the check.
     def ensure_attachment_readable
-      head :not_found unless @book.nil? || @book.published? || @book.accessable?
+      head :not_found unless @book&.published? || @book&.accessable?
     end
 end
diff --git a/test/controllers/action_text/markdown/uploads_controller_test.rb b/test/controllers/action_text/markdown/uploads_controller_test.rb
index 93472f32..029cd30d 100644
--- a/test/controllers/action_text/markdown/uploads_controller_test.rb
+++ b/test/controllers/action_text/markdown/uploads_controller_test.rb
@@ -131,6 +131,21 @@ class ActionText::Markdown::UploadsControllerTest < ActionDispatch::IntegrationT
     assert_response :not_found
   end
 
+  test "an attachment whose owning book can't be resolved is not served" do
+    books(:handbook).update! published: false
+    attachment = attach_upload_to_welcome_page
+
+    # Sever the leaf without cascading the destroy, leaving the attachment live but
+    # its owning book unresolvable. The guard must fail closed on the nil book.
+    pages(:welcome).leaf.delete
+    assert_nil pages(:welcome).reload.owning_book
+
+    reset!
+    get action_text_markdown_upload_path(slug: attachment.slug)
+
+    assert_response :not_found
+  end
+
   test "an attachment of an unpublished book is served to a reader, but not publicly cached" do
     books(:handbook).update! published: false
     attachment = attach_upload_to_welcome_page