diff --git a/packages/app/src/assistant-selection-copy/content.browser.test.ts b/packages/app/src/assistant-selection-copy/content.browser.test.ts
index 00a64406ea..995927f106 100644
--- a/packages/app/src/assistant-selection-copy/content.browser.test.ts
+++ b/packages/app/src/assistant-selection-copy/content.browser.test.ts
@@ -320,6 +320,32 @@ describe("assistant selection copy ranges", () => {
     ).toBe("6. Second bullet text");
   });
 
+  it("keeps the next number when a drag crosses a code block nested in an item", () => {
+    const message = mountFixture();
+    const list = fixtureElement(message, '[data-paseo-markdown-tag="ul"]');
+    list.outerHTML = [
+      '<div data-paseo-markdown-tag="ol" data-paseo-markdown-list-start="1">',
+      '<div data-paseo-markdown-tag="li">',
+      '<div data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">1.</div>',
+      "<div><div><span>Install it:</span></div>",
+      '<div data-paseo-markdown-tag="pre" data-paseo-markdown-language="sh">',
+      '<div data-paseo-markdown-tag="code"><span>brew install foo</span></div>',
+      '<button data-paseo-markdown-ignore="true">Copy</button>',
+      "</div></div>",
+      "</div>",
+      '<div data-paseo-markdown-tag="li">',
+      '<div data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">2.</div>',
+      "<div><div><span>Done.</span></div></div>",
+      "</div>",
+      "</div>",
+    ].join("");
+
+    const content = copyAcross(message, "Install it:", "Done.");
+
+    expect(content?.plainText).toBe("Install it:\n\n```sh\nbrew install foo\n```\n\n2. Done.");
+    expect(content?.html).toContain("<div>2. Done.</div>");
+  });
+
   it("retains nested markers when a drag includes the complete outer item", () => {
     const message = mountFixture();
     const firstItem = fixtureElement(message, '[data-paseo-markdown-tag="li"]');
diff --git a/packages/app/src/assistant-selection-copy/content.web.ts b/packages/app/src/assistant-selection-copy/content.web.ts
index aa6e6cd91b..ac4643b2ff 100644
--- a/packages/app/src/assistant-selection-copy/content.web.ts
+++ b/packages/app/src/assistant-selection-copy/content.web.ts
@@ -53,9 +53,7 @@ turndown.addRule("compactListItem", {
     if (parent?.nodeName !== "OL") {
       return `${options.bulletListMarker} ${item}\n`;
     }
-    const start = Number(parent.getAttribute("start") ?? 1);
-    const index = Array.from(parent.children).indexOf(node);
-    return `${start + index}. ${item}\n`;
+    return `${node.getAttribute("value")}. ${item}\n`;
   },
 });
 
@@ -536,6 +534,7 @@ function restoreMarkdownElements(container: HTMLElement): void {
       if (start) {
         semanticElement.setAttribute("start", start);
       }
+      numberOrderedListItems(semanticElement, Number(start ?? 1));
     }
     if (tagName === "pre") {
       const language = element.getAttribute(MARKDOWN_COPY_LANGUAGE_ATTRIBUTE);
@@ -568,6 +567,20 @@ function restoreMarkdownElements(container: HTMLElement): void {
   }
 }
 
+/**
+ * Each item carries its number before Turndown re-parses the HTML. Until then every
+ * child of the list is one item, including a partly selected item demoted to a `p`.
+ * The parser splits a `p` that holds a code block into several siblings, so counting
+ * siblings afterwards numbers the next item too high.
+ */
+function numberOrderedListItems(list: Element, start: number): void {
+  Array.from(list.children).forEach((child, index) => {
+    if (child.tagName === "LI") {
+      child.setAttribute("value", String(start + index));
+    }
+  });
+}
+
 function unwrapIncompleteTables(container: HTMLElement): void {
   for (const table of container.querySelectorAll("table")) {
     if (hasUsableTableColumnContract(table)) {