diff --git a/src/browser/tests/node/append_child.html b/src/browser/tests/node/append_child.html
index 151815b9..48bffe91 100644
--- a/src/browser/tests/node/append_child.html
+++ b/src/browser/tests/node/append_child.html
@@ -65,3 +65,32 @@
   assertChildren(['a'], d3);
   testing.expectEqual(null, b.parentNode);
 </script>
+
+<div id=d4></div>
+<div id=d4_stash></div>
+<script id=appendChild_disconnect_callback_reparents>
+  // Moving a connected child into a disconnected target makes
+  // will_be_reconnected=false, so disconnectedCallback fires synchronously
+  // inside removeNode. The callback re-parents the child; appendChild
+  // respects that placement instead of overriding it.
+  const d4 = $('#d4');
+  const stash = $('#d4_stash');
+
+  class ReparentOnDisconnect extends HTMLElement {
+    disconnectedCallback() {
+      if (this.parentNode === null) {
+        stash.appendChild(this);
+      }
+    }
+  }
+  customElements.define('reparent-on-disconnect', ReparentOnDisconnect);
+
+  const rpd = document.createElement('reparent-on-disconnect');
+  rpd.id = 'rpd';
+  d4.appendChild(rpd);
+
+  const detached = document.createElement('div');
+  detached.appendChild(rpd);
+
+  testing.expectEqual(stash, rpd.parentNode);
+</script>
diff --git a/src/browser/tests/node/insert_before.html b/src/browser/tests/node/insert_before.html
index 50dff07c..1018c314 100644
--- a/src/browser/tests/node/insert_before.html
+++ b/src/browser/tests/node/insert_before.html
@@ -39,3 +39,34 @@
   assertChildren([], d1);
   assertChildren([c1, c2], d2);
 </script>
+
+<div id=d3></div>
+<div id=d3_stash></div>
+<script id=insertBefore_disconnect_callback_reparents>
+  // Same disconnectedCallback re-parenting pattern as in append_child.html,
+  // exercised through insertBefore. insertBefore respects the callback's
+  // placement instead of overriding it.
+  const d3 = $('#d3');
+  const stash = $('#d3_stash');
+
+  class IBReparentOnDisconnect extends HTMLElement {
+    disconnectedCallback() {
+      if (this.parentNode === null) {
+        stash.appendChild(this);
+      }
+    }
+  }
+  customElements.define('ib-reparent-on-disconnect', IBReparentOnDisconnect);
+
+  const moving = document.createElement('ib-reparent-on-disconnect');
+  moving.id = 'ib_moving';
+  d3.appendChild(moving);
+
+  const detached = document.createElement('div');
+  const ref = document.createElement('span');
+  detached.appendChild(ref);
+
+  detached.insertBefore(moving, ref);
+
+  testing.expectEqual(stash, moving.parentNode);
+</script>
diff --git a/src/browser/webapi/Node.zig b/src/browser/webapi/Node.zig
index 718c065a..8e8eea21 100644
--- a/src/browser/webapi/Node.zig
+++ b/src/browser/webapi/Node.zig
@@ -253,6 +253,11 @@ pub fn appendChild(self: *Node, child: *Node, frame: *Frame) !*Node {
         try frame.adoptNodeTree(child, child_owner.?, parent_owner);
     }
 
+    // A custom element callback can re-parent the node. If it does, we're done
+    if (child._parent != null) {
+        return child;
+    }
+
     try frame.appendNode(self, child, .{
         .child_already_connected = child_connected,
         .adopting_to_new_document = adopting_to_new_document,
@@ -624,6 +629,22 @@ pub fn insertBefore(self: *Node, new_node: *Node, ref_node_: ?*Node, frame: *Fra
         try frame.adoptNodeTree(new_node, child_owner.?, parent_owner);
     }
 
+    // See Node.appendChild: a callback above (disconnectedCallback or
+    // adoptedCallback) can re-parent new_node. Let that placement stand.
+    if (new_node._parent != null) {
+        return new_node;
+    }
+
+    // The same callback could also have detached ref_node from self. Fall
+    // back to append so new_node still lands in self.
+    if (ref_node._parent != self) {
+        try frame.appendNode(self, new_node, .{
+            .child_already_connected = child_already_connected,
+            .adopting_to_new_document = adopting_to_new_document,
+        });
+        return new_node;
+    }
+
     try frame.insertNodeRelative(
         self,
         new_node,