diff --git a/packages/app/e2e/browser/assistant-selection-copy.spec.ts b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
index 3c9440fdb..d80401deb 100644
--- a/packages/app/e2e/browser/assistant-selection-copy.spec.ts
+++ b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
@@ -118,6 +118,53 @@ async function selectAssistantText(page: Page, text: string): Promise<void> {
   await selectAssistantTextRange(page, text, text);
 }
 
+async function selectAssistantListItemFromMarker(
+  page: Page,
+  listTag: "ol" | "ul",
+  itemText: string,
+  endText: string,
+): Promise<void> {
+  const assistantMessage = page.getByTestId("assistant-message").filter({
+    hasText: "Direct matches:",
+  });
+  const item = assistantMessage
+    .locator(`[data-paseo-markdown-tag="${listTag}"]`)
+    .filter({ hasText: itemText })
+    .locator(':scope > [data-paseo-markdown-tag="li"]')
+    .filter({ hasText: itemText });
+
+  await item.evaluate((element, selectedEndText) => {
+    const marker = element.querySelector(':scope > [data-paseo-markdown-list-marker="true"]');
+    const markerText = marker?.firstChild;
+    if (!(markerText instanceof Text)) {
+      throw new Error("Expected rendered list marker text");
+    }
+
+    const walker = document.createTreeWalker(element, NodeFilter.SHOW_TEXT);
+    let endNode: Text | null = null;
+    let endOffset = -1;
+    while (walker.nextNode()) {
+      const node = walker.currentNode;
+      const offset = node.textContent?.indexOf(selectedEndText) ?? -1;
+      if (node instanceof Text && offset >= 0) {
+        endNode = node;
+        endOffset = offset + selectedEndText.length;
+        break;
+      }
+    }
+    if (!endNode) {
+      throw new Error(`Could not find list item selection end: ${selectedEndText}`);
+    }
+
+    const range = document.createRange();
+    range.setStart(markerText, 0);
+    range.setEnd(endNode, endOffset);
+    const selection = window.getSelection();
+    selection?.removeAllRanges();
+    selection?.addRange(range);
+  }, endText);
+}
+
 async function doubleClickAssistantMarkdownText(
   page: Page,
   tag: "code" | "strong",
@@ -405,6 +452,24 @@ test("copying an assistant selection preserves Markdown structure and links", as
       '<div>- <strong><a href="https://example.com/issues/1">First issue</a></strong>',
     );
 
+    await selectAssistantListItemFromMarker(page, "ul", "First issue", "failure.");
+    await copySelection(page);
+
+    const draggedBulletClipboard = await readRichClipboard(page);
+    expect(draggedBulletClipboard.plainText).toBe(
+      "- **[First issue](https://example.com/issues/1)**: exact `apply_patch` failure.",
+    );
+    expect(draggedBulletClipboard.html).toContain(
+      '<div>- <strong><a href="https://example.com/issues/1">First issue</a></strong>',
+    );
+
+    await selectAssistantListItemFromMarker(page, "ol", "Sixth item", "Sixth item");
+    await copySelection(page);
+
+    const draggedNumberClipboard = await readRichClipboard(page);
+    expect(draggedNumberClipboard.plainText).toBe("6. Sixth item");
+    expect(draggedNumberClipboard.html).toContain("<div>6. Sixth item</div>");
+
     await selectAssistantText(page, "docs");
     await copySelection(page);
 
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 df3269017..c53cba9f9 100644
--- a/packages/app/src/assistant-selection-copy/content.browser.test.ts
+++ b/packages/app/src/assistant-selection-copy/content.browser.test.ts
@@ -5,8 +5,8 @@ const fixture = `
   <div data-testid="assistant-message">
     <div data-paseo-markdown-tag="p">Prefix <span data-paseo-markdown-tag="strong">bold text</span> and <span data-paseo-markdown-tag="code">inline code</span> suffix.</div>
     <div data-paseo-markdown-tag="ul">
-      <div data-paseo-markdown-tag="li"><span data-paseo-markdown-ignore="true">•</span><div><span>First bullet text</span></div></div>
-      <div data-paseo-markdown-tag="li"><span data-paseo-markdown-ignore="true">•</span><div><span>Second bullet text</span></div></div>
+      <div data-paseo-markdown-tag="li"><span data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">•</span><div><span>First bullet text</span></div></div>
+      <div data-paseo-markdown-tag="li"><span data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">•</span><div><span>Second bullet text</span></div></div>
     </div>
     <div data-paseo-markdown-tag="pre" data-paseo-markdown-language="ts"><span data-paseo-markdown-tag="code">const answer = true;</span></div>
   </div>
@@ -203,6 +203,97 @@ describe("assistant selection copy ranges", () => {
     expect(copiedMarkdown(selectNodeContents(item))).toBe("- First bullet text");
   });
 
+  it("retains a bullet when a drag selects from the rendered marker through the item text", () => {
+    const message = mountFixture();
+    const marker = fixtureElement(message, '[data-paseo-markdown-list-marker="true"]');
+    const itemText = fixtureElement(message, '[data-paseo-markdown-tag="li"] div span');
+
+    const content = createAssistantSelectionClipboardContent(
+      selectRange(marker, 0, itemText, textNode(itemText).length),
+    );
+    expect(content?.plainText).toBe("- First bullet text");
+    expect(content?.html).toContain("<div>- First bullet text</div>");
+    expect(content?.html).not.toContain("<ul>");
+    expect(content?.html).not.toContain("<li>");
+  });
+
+  it("retains a bullet when a drag includes the marker and part of the item text", () => {
+    const message = mountFixture();
+    const marker = fixtureElement(message, '[data-paseo-markdown-list-marker="true"]');
+    const itemText = fixtureElement(message, '[data-paseo-markdown-tag="li"] div span');
+
+    expect(copiedMarkdown(selectRange(marker, 0, itemText, 5))).toBe("- First");
+  });
+
+  it("does not invent a bullet when a drag starts after the rendered marker", () => {
+    const message = mountFixture();
+    const marker = fixtureElement(message, '[data-paseo-markdown-list-marker="true"]');
+    const itemText = fixtureElement(message, '[data-paseo-markdown-tag="li"] div span');
+
+    expect(
+      copiedMarkdown(
+        selectRange(marker, textNode(marker).length, itemText, textNode(itemText).length),
+      ),
+    ).toBe("First bullet text");
+  });
+
+  it("retains every selected marker across a partial multi-item drag", () => {
+    const message = mountFixture();
+    const markerSelector = '[data-paseo-markdown-list-marker="true"]';
+    const textSelector = '[data-paseo-markdown-tag="li"] div span';
+    const firstMarker = fixtureElement(message, markerSelector);
+    const secondText = fixtureElement(message, textSelector, 1);
+
+    expect(copiedMarkdown(selectRange(firstMarker, 0, secondText, 6))).toBe(
+      "- First bullet text\n- Second",
+    );
+  });
+
+  it("retains the original number when a marker drag starts mid-list", () => {
+    const message = mountFixture();
+    const list = fixtureElement(message, '[data-paseo-markdown-tag="ul"]');
+    list.setAttribute("data-paseo-markdown-tag", "ol");
+    list.setAttribute("data-paseo-markdown-list-start", "5");
+    const markers = list.querySelectorAll<HTMLElement>('[data-paseo-markdown-list-marker="true"]');
+    markers.item(0).textContent = "5.";
+    markers.item(1).textContent = "6.";
+    const secondMarker = fixtureElement(list, '[data-paseo-markdown-list-marker="true"]', 1);
+    const secondText = fixtureElement(list, '[data-paseo-markdown-tag="li"] div span', 1);
+
+    expect(
+      copiedMarkdown(selectRange(secondMarker, 0, secondText, textNode(secondText).length)),
+    ).toBe("6. Second bullet text");
+  });
+
+  it("retains nested markers when a drag includes the complete outer item", () => {
+    const message = mountFixture();
+    const firstItem = fixtureElement(message, '[data-paseo-markdown-tag="li"]');
+    firstItem.innerHTML = [
+      '<span data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">•</span>',
+      "<div>",
+      "<span>Outer text</span>",
+      '<div data-paseo-markdown-tag="ul">',
+      '<div data-paseo-markdown-tag="li">',
+      '<span data-paseo-markdown-ignore="true" data-paseo-markdown-list-marker="true">•</span>',
+      "<div><span>Inner text</span></div>",
+      "</div>",
+      "</div>",
+      "</div>",
+    ].join("");
+    const outerMarker = fixtureElement(
+      firstItem,
+      ':scope > [data-paseo-markdown-list-marker="true"]',
+    );
+    const innerText = fixtureElement(
+      firstItem,
+      ':scope [data-paseo-markdown-tag="ul"] > [data-paseo-markdown-tag="li"] > div > span',
+    );
+
+    expect(copiedMarkdown(selectRange(outerMarker, 0, innerText, textNode(innerText).length))).toBe(
+      "- Outer text\n    - Inner text",
+    );
+  });
+
   it("preserves paragraph breaks when rich HTML flattens a loose list item", () => {
     const message = mountFixture();
     const item = 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 6678e4a5b..f04ddfb3e 100644
--- a/packages/app/src/assistant-selection-copy/content.web.ts
+++ b/packages/app/src/assistant-selection-copy/content.web.ts
@@ -9,6 +9,7 @@ import {
   MARKDOWN_COPY_ALIGN_ATTRIBUTE,
   MARKDOWN_COPY_IGNORE_ATTRIBUTE,
   MARKDOWN_COPY_LANGUAGE_ATTRIBUTE,
+  MARKDOWN_COPY_LIST_MARKER_ATTRIBUTE,
   MARKDOWN_COPY_LIST_START_ATTRIBUTE,
   MARKDOWN_COPY_TAG_ATTRIBUTE,
   MARKDOWN_COPY_UNWRAP_ATTRIBUTE,
@@ -278,7 +279,7 @@ function shouldPreserveSemanticElement(range: Range, element: Element): boolean
   if (tag === "p" || isTableStructure(tag)) {
     return true;
   }
-  const isSelectableSemantic = tag !== null && tag !== "ol" && tag !== "ul";
+  const isSelectableSemantic = tag !== null && tag !== "li" && tag !== "ol" && tag !== "ul";
   if (
     (isSelectableSemantic || element.tagName === "A") &&
     selectionStaysInsideElement(range, element)
@@ -287,7 +288,12 @@ function shouldPreserveSemanticElement(range: Range, element: Element): boolean
   }
   if (tag === "ol" || tag === "ul") {
     const selectedItems = selectedListItems(element, range);
-    return selectedItems.some((item) => hasSelectedAllContents(range, item, true));
+    return selectedItems.some(
+      (item) => hasSelectedListMarker(range, item) || hasSelectedAllContents(range, item, true),
+    );
+  }
+  if (tag === "li" && hasSelectedListMarker(range, element)) {
+    return true;
   }
   return hasSelectedAllContents(range, element, tag === "li");
 }
@@ -311,6 +317,31 @@ function selectedListItems(list: Element, range: Range): Element[] {
   );
 }
 
+function hasSelectedListMarker(range: Range, item: Element): boolean {
+  const marker = item.querySelector(`:scope > [${MARKDOWN_COPY_LIST_MARKER_ATTRIBUTE}]`);
+  if (!marker) {
+    return false;
+  }
+
+  const markerContents = document.createRange();
+  markerContents.selectNodeContents(marker);
+  const selectionEndsBeforeMarker =
+    range.compareBoundaryPoints(Range.END_TO_START, markerContents) >= 0;
+  const selectionStartsAfterMarker =
+    range.compareBoundaryPoints(Range.START_TO_END, markerContents) <= 0;
+  if (selectionEndsBeforeMarker || selectionStartsAfterMarker) {
+    return false;
+  }
+
+  if (range.compareBoundaryPoints(Range.START_TO_START, markerContents) > 0) {
+    markerContents.setStart(range.startContainer, range.startOffset);
+  }
+  if (range.compareBoundaryPoints(Range.END_TO_END, markerContents) < 0) {
+    markerContents.setEnd(range.endContainer, range.endOffset);
+  }
+  return hasMarkdownContent(markerContents.cloneContents(), true);
+}
+
 function normalizeOrderedListStart(copy: Element, original: Element, range: Range): void {
   if (original.getAttribute(MARKDOWN_COPY_TAG_ATTRIBUTE) !== "ol") {
     return;
diff --git a/packages/app/src/assistant-selection-copy/markup.ts b/packages/app/src/assistant-selection-copy/markup.ts
index 59a372a53..8f220043c 100644
--- a/packages/app/src/assistant-selection-copy/markup.ts
+++ b/packages/app/src/assistant-selection-copy/markup.ts
@@ -1,5 +1,6 @@
 export const MARKDOWN_COPY_TAG_ATTRIBUTE = "data-paseo-markdown-tag";
 export const MARKDOWN_COPY_IGNORE_ATTRIBUTE = "data-paseo-markdown-ignore";
+export const MARKDOWN_COPY_LIST_MARKER_ATTRIBUTE = "data-paseo-markdown-list-marker";
 export const MARKDOWN_COPY_UNWRAP_ATTRIBUTE = "data-paseo-markdown-unwrap";
 export const MARKDOWN_COPY_LIST_START_ATTRIBUTE = "data-paseo-markdown-list-start";
 export const MARKDOWN_COPY_LANGUAGE_ATTRIBUTE = "data-paseo-markdown-language";
@@ -28,6 +29,7 @@ export const markdownCopyDataSet = {
   hr: { paseoMarkdownTag: "hr" },
   ignore: { paseoMarkdownIgnore: "true" },
   li: { paseoMarkdownTag: "li" },
+  listMarker: { paseoMarkdownIgnore: "true", paseoMarkdownListMarker: "true" },
   ol: { paseoMarkdownTag: "ol" },
   p: { paseoMarkdownTag: "p" },
   pre: { paseoMarkdownTag: "pre" },
diff --git a/packages/app/src/components/message.tsx b/packages/app/src/components/message.tsx
index 2cc7cb402..e2e54fa77 100644
--- a/packages/app/src/components/message.tsx
+++ b/packages/app/src/components/message.tsx
@@ -1806,7 +1806,7 @@ export const AssistantMessage = memo(function AssistantMessage({
 
         return (
           <View key={node.key} style={styles.list_item} dataSet={markdownCopyDataSet.li}>
-            <Text style={iconStyle} dataSet={markdownCopyDataSet.ignore}>
+            <Text style={iconStyle} dataSet={markdownCopyDataSet.listMarker}>
               {marker}
             </Text>
             <MarkdownListItemContent contentStyle={contentStyle}>