diff --git a/crates/mdbook-html/front-end/templates/toc.js.hbs b/crates/mdbook-html/front-end/templates/toc.js.hbs
index 1a9f751ccf..ae61a45d64 100644
--- a/crates/mdbook-html/front-end/templates/toc.js.hbs
+++ b/crates/mdbook-html/front-end/templates/toc.js.hbs
@@ -335,10 +335,25 @@ window.customElements.define('mdbook-sidebar-scrollbox', MDBookSidebarScrollbox)
         });
     }
 
+    // Returns the node to copy header text from. When the heading uses an
+    // empty `.header` link as its first child (see issue #221), use the full
+    // heading so the sidebar still shows the title text.
+    function headerContentRoot(header) {
+        const first = header.children[0];
+        if (first?.tagName === 'A' && first.classList.contains('header')) {
+            if (first.textContent.trim() === '') {
+                return header;
+            }
+            return first;
+        }
+        return first;
+    }
+
     // Takes the nodes from the given head and copies them over to the
     // destination, along with some filtering.
     function filterHeader(source, dest) {
         const clone = source.cloneNode(true);
+        clone.querySelectorAll('a.header').forEach(a => a.remove());
         clone.querySelectorAll('mark').forEach(mark => {
             mark.replaceWith(...mark.childNodes);
         });
@@ -417,7 +432,7 @@ window.customElements.define('mdbook-sidebar-scrollbox', MDBookSidebarScrollbox)
             span.appendChild(a);
             a.href = '#' + header.id;
             a.classList.add('header-in-summary');
-            filterHeader(header.children[0], a);
+            filterHeader(headerContentRoot(header), a);
             a.addEventListener('click', headerThresholdClick);
             const nextHeader = headers[i + 1];
             if (nextHeader !== undefined) {
diff --git a/crates/mdbook-html/src/html/tree.rs b/crates/mdbook-html/src/html/tree.rs
index 5cb97ce378..a085b4f81b 100644
--- a/crates/mdbook-html/src/html/tree.rs
+++ b/crates/mdbook-html/src/html/tree.rs
@@ -932,15 +932,26 @@ where
                 el.insert_attr("id", id.into());
                 href
             };
-            // Insert an <a> element between the heading and its children.
             let mut a = Element::new("a");
             a.insert_attr("class", "header".into());
             a.insert_attr("href", href.into());
-            let mut a = self.tree.orphan(Node::Element(a));
-            a.reparent_from_id_append(heading);
-            let a_id = a.id();
-            let mut node = self.tree.get_mut(heading).unwrap();
-            node.append_id(a_id);
+
+            let heading_node = self.tree.get(heading).unwrap();
+            if heading_contains_nested_anchor(heading_node) {
+                // Prepend an empty header link so headings may contain other
+                // links without nesting `<a>` elements (issue #221).
+                self.tree
+                    .get_mut(heading)
+                    .unwrap()
+                    .prepend(Node::Element(a));
+            } else {
+                // Insert an `<a>` element between the heading and its children.
+                let mut a = self.tree.orphan(Node::Element(a));
+                a.reparent_from_id_append(heading);
+                let a_id = a.id();
+                let mut node = self.tree.get_mut(heading).unwrap();
+                node.append_id(a_id);
+            }
         }
     }
 
@@ -1074,6 +1085,27 @@ where
 /// Traverse the given node, emitting any plain text into the output.
 ///
 /// This is used to generate the `id` of a header.
+/// Returns true if the heading contains an `<a>` element from the markdown source.
+fn heading_contains_nested_anchor(node: NodeRef<'_, Node>) -> bool {
+    for child in node.children() {
+        match child.value() {
+            Node::Element(el) if el.name() == "a" => return true,
+            Node::Element(_) => {
+                if heading_contains_nested_anchor(child) {
+                    return true;
+                }
+            }
+            Node::Fragment => {
+                if heading_contains_nested_anchor(child) {
+                    return true;
+                }
+            }
+            Node::Text(_) | Node::Comment(_) | Node::RawData(_) => {}
+        }
+    }
+    false
+}
+
 fn text_in_node(node: NodeRef<'_, Node>, output: &mut String) {
     for child in node.children() {
         match child.value() {
diff --git a/tests/testsuite/markdown/definition_lists/expected/definition_lists.html b/tests/testsuite/markdown/definition_lists/expected/definition_lists.html
index c647ccb4dd..bcc03a40b4 100644
--- a/tests/testsuite/markdown/definition_lists/expected/definition_lists.html
+++ b/tests/testsuite/markdown/definition_lists/expected/definition_lists.html
@@ -22,7 +22,7 @@ <h1 id="definition-lists"><a class="header" href="#definition-lists">Definition
 </dl>
 <h2 id="term-with-link"><a class="header" href="#term-with-link">Term with link</a></h2>
 <dl>
-<dt id="apple-2"><a class="header" href="#apple-2"><a href="some-page.html#apple">apple</a></a></dt>
+<dt id="apple-2"><a class="header" href="#apple-2"></a><a href="some-page.html#apple">apple</a></dt>
 <dd>red fruit</dd>
 </dl>
 <h2 id="multi-line-term"><a class="header" href="#multi-line-term">Multi-line term</a></h2>
diff --git a/tests/testsuite/rendering/header_links/expected/header_links.html b/tests/testsuite/rendering/header_links/expected/header_links.html
index 29c35a530d..101ed49951 100644
--- a/tests/testsuite/rendering/header_links/expected/header_links.html
+++ b/tests/testsuite/rendering/header_links/expected/header_links.html
@@ -1,4 +1,5 @@
 <h1 id="header-links"><a class="header" href="#header-links">Header Links</a></h1>
+<h2 id="header-with-link"><a class="header" href="#header-with-link"></a>Header with <a href="https://example.com">link</a>.</h2>
 <h2 id="foobar"><a class="header" href="#foobar">Foo^bar</a></h2>
 <h3 id=""><a class="header" href="#"></a></h3>
 <h4 id="-1"><a class="header" href="#-1"></a></h4>
@@ -7,4 +8,4 @@ <h2 id="repeat"><a class="header" href="#repeat">Repeat</a></h2>
 <h2 id="repeat-1"><a class="header" href="#repeat-1">Repeat</a></h2>
 <h2 id="repeat-2"><a class="header" href="#repeat-2">Repeat</a></h2>
 <h2 id="repeat-1-1"><a class="header" href="#repeat-1-1">Repeat 1</a></h2>
-<h2 id="with-emphasis-bold-bold_emphasis-code-escaped-html-link-httpsexamplecom"><a class="header" href="#with-emphasis-bold-bold_emphasis-code-escaped-html-link-httpsexamplecom"><!--comment--> With <em>emphasis</em> <strong>bold</strong> <strong><em>bold_emphasis</em></strong> <code>code</code> &lt;escaped&gt; <span>html</span> <a href="https://example.com/link">link</a> <a href="https://example.com/">https://example.com/</a></a></h2>
\ No newline at end of file
+<h2 id="with-emphasis-bold-bold_emphasis-code-escaped-html-link-httpsexamplecom"><a class="header" href="#with-emphasis-bold-bold_emphasis-code-escaped-html-link-httpsexamplecom"></a><!--comment--> With <em>emphasis</em> <strong>bold</strong> <strong><em>bold_emphasis</em></strong> <code>code</code> &lt;escaped&gt; <span>html</span> <a href="https://example.com/link">link</a> <a href="https://example.com/">https://example.com/</a></h2>
\ No newline at end of file
diff --git a/tests/testsuite/rendering/header_links/src/header_links.md b/tests/testsuite/rendering/header_links/src/header_links.md
index 8ad556f7a7..d747ce997d 100644
--- a/tests/testsuite/rendering/header_links/src/header_links.md
+++ b/tests/testsuite/rendering/header_links/src/header_links.md
@@ -1,5 +1,7 @@
 # Header Links
 
+## Header with [link](https://example.com).
+
 ## Foo^bar
 
 ###