diff --git a/src/browser/features/Messages/ChunkedStreamingMarkdown.test.tsx b/src/browser/features/Messages/ChunkedStreamingMarkdown.test.tsx
index 1c0e1616a11..b5d35f04558 100644
--- a/src/browser/features/Messages/ChunkedStreamingMarkdown.test.tsx
+++ b/src/browser/features/Messages/ChunkedStreamingMarkdown.test.tsx
@@ -125,4 +125,67 @@ describe("ChunkedStreamingMarkdown", () => {
     expect(expected.length).toBeGreaterThan(100);
     expect(chunked).toEqual(expected);
   });
+
+  // #5664: a loose list longer than a chunk, streamed item by item. Some frames end mid-marker
+  // (`…\n\n30` before the `.`), where the partial marker parses as a paragraph after the list.
+  test.each([
+    ["ordered", (k: number) => `${k}.`],
+    ["bullet", () => "-"],
+  ])(
+    "a loose %s list streamed across chunks renders like one static render",
+    async (_kind, marker) => {
+      const items = Array.from(
+        { length: 60 },
+        (_, i) =>
+          `${marker(i + 1)} Item ${i + 1} with **bold** and more words, lorem ipsum dolor sit.`
+      );
+      const reply = items.join("\n\n");
+      const renderRow = (content: string, isStreaming: boolean) =>
+        flushSync(() =>
+          root?.render(
+            <ThemeProvider forcedTheme="dark">
+              <ChunkedStreamingMarkdown content={content} isStreaming={isStreaming} />
+            </ThemeProvider>
+          )
+        );
+      let text = "";
+      for (const item of items) {
+        if (text.length > 0) {
+          text += "\n\n";
+          // Every partial marker is its own frame, then the whole item.
+          const space = item.indexOf(" ");
+          for (let end = 1; end <= space; end++) renderRow(text + item.slice(0, end), true);
+        }
+        text += item;
+        renderRow(text, true);
+      }
+      renderRow(reply, false);
+      for (let i = 0; i < 100 && !container.textContent?.includes("Item 1 with"); i++) {
+        await new Promise((resolve) => setTimeout(resolve, 20));
+      }
+
+      // Structure, not just text: one list with a <p> in every item, exactly as one render.
+      const outline = (element: Element) =>
+        [...element.querySelectorAll("ol, ul, li, li > p")].map(
+          (node) => `${node.tagName}${node.getAttribute("start") ?? ""}`
+        );
+      const single = document.createElement("div");
+      document.body.appendChild(single);
+      const singleRoot = createRoot(single);
+      flushSync(() =>
+        singleRoot.render(
+          <ThemeProvider forcedTheme="dark">
+            <MarkdownCore content={reply} />
+          </ThemeProvider>
+        )
+      );
+      const expected = outline(single);
+      const expectedText = single.textContent?.replace(/\s+/g, "");
+      flushSync(() => singleRoot.unmount());
+
+      expect(expected.filter((tag) => tag === "LI")).toHaveLength(60);
+      expect(outline(container)).toEqual(expected);
+      expect(container.textContent?.replace(/\s+/g, "")).toBe(expectedText);
+    }
+  );
 });
diff --git a/src/browser/features/Messages/ChunkedStreamingMarkdown.tsx b/src/browser/features/Messages/ChunkedStreamingMarkdown.tsx
index 4441138b628..2dc083b8a0d 100644
--- a/src/browser/features/Messages/ChunkedStreamingMarkdown.tsx
+++ b/src/browser/features/Messages/ChunkedStreamingMarkdown.tsx
@@ -8,6 +8,9 @@ import {
 import { MarkdownCore } from "./MarkdownCore";
 import { normalizeMarkdown } from "./MarkdownStyles";
 
+// Blank lines, or the digits of an ordered list marker before its `.` or `)` arrives.
+const PARTIAL_LIST_MARKER = /^\d{0,9}$/;
+
 /**
  * Splits growing markdown into chunks of whole Streamdown blocks, about `maxChars` each, and
  * joins back to the input. A chunk is sealed once a later block follows it: the last block can
@@ -32,8 +35,19 @@ export class MarkdownChunker {
     }
     const groups: string[] = [];
     let current = "";
-    for (const block of parseMarkdownIntoBlocks(text.slice(this.sealedText.length))) {
-      if (current.length > 0 && current.length + block.length > this.maxChars) {
+    const blocks = parseMarkdownIntoBlocks(text.slice(this.sealedText.length));
+    // A tail that is only a partial list marker (`…\n\n30` before its `.`) parses as a paragraph
+    // after the list, but joins the list once the marker is complete (#5664). So that tail and
+    // the blank lines before it never start a group: sealing the list there would make the next
+    // item start a second list.
+    let tailStart = blocks.length;
+    while (tailStart > 0 && PARTIAL_LIST_MARKER.test(blocks[tailStart - 1].trim())) tailStart--;
+    for (const [index, block] of blocks.entries()) {
+      if (
+        index < tailStart &&
+        current.length > 0 &&
+        current.length + block.length > this.maxChars
+      ) {
         groups.push(current);
         current = "";
       }
@@ -103,7 +117,13 @@ export const ChunkedStreamingMarkdown: React.FC<ChunkedStreamingMarkdownProps> =
     <div className="space-y-2">
       {chunks.slice(start).map((chunk, offset) => (
         <MarkdownCore
-          key={start + offset}
+          // Streamdown memoizes each element by its source position, so an element whose
+          // position did not change keeps a stale render: the first item of a list that turns
+          // loose keeps no <p>. A chunk therefore mounts fresh when it is sealed and when the
+          // stream ends (#5664). A sealed chunk keeps its key, so MarkdownCore's memo still skips it.
+          key={
+            props.isStreaming && start + offset === lastIndex ? `open-${lastIndex}` : start + offset
+          }
           content={chunk}
           // Only the open last chunk can hold incomplete markdown.
           parseIncompleteMarkdown={props.isStreaming && start + offset === lastIndex}