From 748373c68b799c5f8759c04d11fbde252898b3c9 Mon Sep 17 00:00:00 2001
From: Dominic R <dominic@sdko.org>
Date: Sat, 12 Sep 2026 19:06:12 -0400
Subject: [PATCH] fix(web): keep nested task states out of parent bullets

---
 apps/web/src/markdown-clipboard.test.ts | 71 +++++++++++++++++++++++--
 apps/web/src/markdown-clipboard.ts      |  4 +-
 2 files changed, 71 insertions(+), 4 deletions(-)

diff --git a/apps/web/src/markdown-clipboard.test.ts b/apps/web/src/markdown-clipboard.test.ts
index 9296967e4b82..a08dc299161b 100644
--- a/apps/web/src/markdown-clipboard.test.ts
+++ b/apps/web/src/markdown-clipboard.test.ts
@@ -19,6 +19,7 @@ class FakeText {
 
 class FakeElement {
   readonly nodeType = ELEMENT_NODE;
+  checked = false;
   readonly childNodes: Array<FakeElement | FakeText> = [];
   readonly classList = {
     contains: (name: string) => this.classNames.includes(name),
@@ -61,18 +62,31 @@ class FakeElement {
 
   /** Supports only the selectors markdown-clipboard actually asks for. */
   querySelector(selector: string): FakeElement | null {
+    if (selector.includes(", ")) {
+      for (const part of selector.split(", ")) {
+        const match = this.querySelector(part);
+        if (match) return match;
+      }
+      return null;
+    }
     const childOnly = selector.startsWith(":scope > ");
-    const target = childOnly ? selector.slice(":scope > ".length) : selector;
+    const [target, ...rest] = (childOnly ? selector.slice(":scope > ".length) : selector).split(
+      " > ",
+    );
     const matches = (element: FakeElement): boolean => {
       if (target === 'input[type="checkbox"]') {
         return element.tagName === "INPUT" && element.getAttribute("type") === "checkbox";
       }
-      return element.tagName === target.toUpperCase();
+      return element.tagName === target?.toUpperCase();
     };
     const search = (parent: FakeElement): FakeElement | null => {
       for (const child of parent.childNodes) {
         if (!(child instanceof FakeElement)) continue;
-        if (matches(child)) return child;
+        if (matches(child)) {
+          if (rest.length === 0) return child;
+          const nested = child.querySelector(`:scope > ${rest.join(" > ")}`);
+          if (nested) return nested;
+        }
         if (!childOnly) {
           const nested = search(child);
           if (nested) return nested;
@@ -143,6 +157,57 @@ describe("serializeRenderedMarkdownFragment", () => {
     expect(serializeRenderedMarkdownFragment(asNode(container))).toBe("run `git status` first");
   });
 
+  describe.each([
+    { parentLayout: "tight", childLayout: "tight" },
+    { parentLayout: "tight", childLayout: "loose" },
+    { parentLayout: "loose", childLayout: "tight" },
+    { parentLayout: "loose", childLayout: "loose" },
+  ])("$parentLayout parent with $childLayout child", ({ parentLayout, childLayout }) => {
+    it.each([
+      { parentChecked: null, childChecked: true, parent: "- Parent", child: "  - [x] Child" },
+      {
+        parentChecked: false,
+        childChecked: true,
+        parent: "- [ ] Parent",
+        child: "      - [x] Child",
+      },
+      {
+        parentChecked: true,
+        childChecked: false,
+        parent: "- [x] Parent",
+        child: "      - [ ] Child",
+      },
+    ])("copies $parent with $child", ({ parentChecked, childChecked, parent, child }) => {
+      const parentContent = parentLayout === "loose" ? new FakeElement("P") : new FakeElement("LI");
+      if (parentChecked !== null) {
+        const checkbox = new FakeElement("INPUT", [], { type: "checkbox" });
+        checkbox.checked = parentChecked;
+        parentContent.append(checkbox, new FakeText(" "));
+      }
+      parentContent.append(new FakeText("Parent"));
+      const parentItem =
+        parentLayout === "loose" ? new FakeElement("LI").append(parentContent) : parentContent;
+      const checkbox = new FakeElement("INPUT", [], { type: "checkbox" });
+      checkbox.checked = childChecked;
+      const childContent = new FakeElement(childLayout === "loose" ? "P" : "LI").append(
+        checkbox,
+        new FakeText(" Child"),
+      );
+      const childItem =
+        childLayout === "loose" ? new FakeElement("LI").append(childContent) : childContent;
+      parentItem.append(new FakeText("\n"), new FakeElement("UL").append(childItem));
+      const container = new FakeElement("DIV").append(
+        new FakeElement("P").append(new FakeText("Before")),
+        new FakeElement("UL").append(parentItem),
+        new FakeElement("P").append(new FakeText("After")),
+      );
+
+      expect(serializeRenderedMarkdownFragment(asNode(container))).toBe(
+        `Before\n\n${parent}${parentLayout === "loose" ? "\n\n" : "\n"}${child}\n\nAfter`,
+      );
+    });
+  });
+
   it("copies the complete quote, source, and comment instead of the comment-only chip label", () => {
     const citation = {
       version: 1 as const,
diff --git a/apps/web/src/markdown-clipboard.ts b/apps/web/src/markdown-clipboard.ts
index 4a96c8b31d13..39b941801638 100644
--- a/apps/web/src/markdown-clipboard.ts
+++ b/apps/web/src/markdown-clipboard.ts
@@ -119,7 +119,9 @@ function serializeTable(table: Element): string {
 }
 
 function serializeListItem(item: Element, ordered: boolean, index: number): string {
-  const checkbox = item.querySelector('input[type="checkbox"]');
+  const checkbox = item.querySelector(
+    ':scope > input[type="checkbox"], :scope > p > input[type="checkbox"]',
+  );
   const task = checkbox ? `[${(checkbox as HTMLInputElement).checked ? "x" : " "}] ` : "";
   const marker = ordered ? `${index}. ${task}` : `- ${task}`;
   let content = serializeChildren(item)