diff --git a/app/assets/stylesheets/layout.css b/app/assets/stylesheets/layout.css
index 8450fab4..351ff9c3 100644
--- a/app/assets/stylesheets/layout.css
+++ b/app/assets/stylesheets/layout.css
@@ -93,15 +93,19 @@ body {
   }
 }
 
+/* The sidebar spans all four grid rows, so sizing it against its grid area makes
+   it as tall as the whole document and its overflow never kicks in. Stick it to
+   the viewport instead, so the table of contents scrolls its own content. */
 :where(#sidebar) {
   background-color: var(--color-subtle-light);
-  block-size: 100%;
+  block-size: 100dvh;
   font-size: var(--font-medium-responsive);
   grid-area: sidebar;
   inline-size: 25vw;
-  max-block-size: 100%;
+  inset-block-start: 0;
+  max-block-size: 100dvh;
   overflow: auto;
-  position: relative;
+  position: sticky;
   transition: margin-inline-start 0.2s ease-out;
 
   :has(#sidebar-toggle:checked) & {
diff --git a/test/system/sidebar_scroll_test.rb b/test/system/sidebar_scroll_test.rb
new file mode 100644
index 00000000..ab7b9c66
--- /dev/null
+++ b/test/system/sidebar_scroll_test.rb
@@ -0,0 +1,41 @@
+require "application_system_test_case"
+
+class SidebarScrollTest < ApplicationSystemTestCase
+  setup do
+    sign_in "kevin@example.com"
+
+    leaves(:welcome_page).leafable.update! body: ([ "A paragraph of the book." ] * 400).join("\n\n")
+
+    visit leafable_slug_path(leaves(:welcome_page))
+    find("label.sidebar__toggle").click
+
+    assert_operator document_height, :>, viewport_height * 2,
+      "the test page should be considerably taller than the viewport"
+  end
+
+  test "the table of contents fits the viewport instead of the page" do
+    assert_operator sidebar_height, :<=, viewport_height,
+      "the sidebar is #{sidebar_height}px tall in a #{viewport_height}px viewport: " \
+      "it grows with the length of the page instead of staying within the screen"
+  end
+
+  test "the table of contents stays put while the page scrolls" do
+    execute_script "window.scrollTo(0, document.documentElement.scrollHeight)"
+
+    assert_equal 0, sidebar_top.round,
+      "the sidebar scrolled away with the page instead of staying in view"
+  end
+
+  private
+    def viewport_height = evaluate_script("window.innerHeight")
+
+    def document_height = evaluate_script("document.documentElement.scrollHeight")
+
+    def sidebar_height = sidebar_rect["height"]
+
+    def sidebar_top = sidebar_rect["top"]
+
+    def sidebar_rect
+      evaluate_script("document.querySelector('#sidebar').getBoundingClientRect().toJSON()")
+    end
+end