diff --git a/packages/views/editor/extensions/markdown-paste.test.ts b/packages/views/editor/extensions/markdown-paste.test.ts
index 886d71c64..85e6c81b8 100644
--- a/packages/views/editor/extensions/markdown-paste.test.ts
+++ b/packages/views/editor/extensions/markdown-paste.test.ts
@@ -43,6 +43,18 @@ function paste(editor: Editor, text: string, html?: string): boolean {
   );
 }
 
+function pasteThroughEditorDom(editor: Editor, text: string, html: string): void {
+  const event = new Event("paste", { bubbles: false, cancelable: true });
+  Object.defineProperty(event, "clipboardData", {
+    value: {
+      files: [],
+      getData: (type: string) =>
+        type === "text/plain" ? text : type === "text/html" ? html : "",
+    },
+  });
+  editor.view.dom.dispatchEvent(event);
+}
+
 interface JsonNode {
   type: string;
   text?: string;
@@ -187,6 +199,92 @@ describe("markdownPaste — code block context", () => {
     expect(parseSpy).not.toHaveBeenCalled();
   });
 
+  it("keeps ordered numbering when rich HTML fragments every item into its own list", () => {
+    editor = makeEditor({
+      type: "doc",
+      content: [{ type: "paragraph" }],
+    });
+
+    pasteThroughEditorDom(
+      editor,
+      "1. First\n2. Second\n3. Third",
+      "<ol><li><strong>First</strong></li></ol>" +
+        "<ol><li>Second</li></ol>" +
+        "<ol><li>Third</li></ol>",
+    );
+
+    const json = editor.getJSON() as JsonNode;
+    const orderedLists = (json.content ?? []).filter(
+      (node) => node.type === "orderedList",
+    );
+    expect(orderedLists).toHaveLength(1);
+    expect(orderedLists[0]?.content?.map(nodeText)).toEqual([
+      "First",
+      "Second",
+      "Third",
+    ]);
+    expect(editor.getMarkdown()).toContain(
+      "1. **First**\n2. Second\n3. Third",
+    );
+  });
+
+  it("repairs fragmented ordered lists nested inside another list item", () => {
+    editor = makeEditor({
+      type: "doc",
+      content: [{ type: "paragraph" }],
+    });
+
+    pasteThroughEditorDom(
+      editor,
+      "Plan\n1. First\n2. Second",
+      "<ul><li>Plan" +
+        "<ol><li>First</li></ol>" +
+        "<ol><li>Second</li></ol>" +
+        "</li></ul>",
+    );
+
+    const orderedList = findFirst(editor.getJSON() as JsonNode, "orderedList");
+    expect(orderedList?.content?.map(nodeText)).toEqual(["First", "Second"]);
+  });
+
+  it("keeps ordered lists separate when real content divides them", () => {
+    editor = makeEditor({
+      type: "doc",
+      content: [{ type: "paragraph" }],
+    });
+
+    pasteThroughEditorDom(
+      editor,
+      "1. First\nSeparate section\n1. Restarted",
+      "<ol><li>First</li></ol>" +
+        "<p>Separate section</p>" +
+        "<ol><li>Restarted</li></ol>",
+    );
+
+    const json = editor.getJSON() as JsonNode;
+    expect(
+      (json.content ?? []).filter((node) => node.type === "orderedList"),
+    ).toHaveLength(2);
+  });
+
+  it("leaves ProseMirror-owned clipboard slices on the native path", () => {
+    editor = makeEditor({
+      type: "doc",
+      content: [{ type: "paragraph" }],
+    });
+
+    const handled = paste(
+      editor,
+      "1. First\n1. Restarted",
+      '<div data-pm-slice="0 0 []">' +
+        "<ol><li>First</li></ol>" +
+        "<ol><li>Restarted</li></ol>" +
+        "</div>",
+    );
+
+    expect(handled).toBe(false);
+  });
+
   it("does not paste rich HTML natively when its text would drop raw tag-like lines", () => {
     editor = makeEditor({
       type: "doc",
diff --git a/packages/views/editor/extensions/markdown-paste.ts b/packages/views/editor/extensions/markdown-paste.ts
index bdcdee5c3..2b188a770 100644
--- a/packages/views/editor/extensions/markdown-paste.ts
+++ b/packages/views/editor/extensions/markdown-paste.ts
@@ -27,7 +27,11 @@
  */
 import { Extension } from "@tiptap/core";
 import { Plugin, PluginKey } from "@tiptap/pm/state";
-import { Slice } from "@tiptap/pm/model";
+import {
+  Fragment,
+  Slice,
+  type Node as ProseMirrorNode,
+} from "@tiptap/pm/model";
 
 const LARGE_PASTE_TEXT_THRESHOLD = 50_000;
 const SEMANTIC_RICH_HTML_SELECTOR = [
@@ -347,6 +351,62 @@ function classifyPaste({
   return "markdown";
 }
 
+function canJoinOrderedLists(
+  left: ProseMirrorNode,
+  right: ProseMirrorNode,
+): boolean {
+  const leftType = left.attrs.type ?? "1";
+  const rightType = right.attrs.type ?? "1";
+  if (
+    left.type.name !== "orderedList" ||
+    right.type !== left.type ||
+    leftType !== rightType
+  ) {
+    return false;
+  }
+
+  const parsedLeftStart = Number(left.attrs.start);
+  const parsedRightStart = Number(right.attrs.start);
+  const leftStart = Number.isFinite(parsedLeftStart) ? parsedLeftStart : 1;
+  const rightStart = Number.isFinite(parsedRightStart) ? parsedRightStart : 1;
+  const expectedContinuation = leftStart + left.childCount;
+
+  // Some rich-text sources put every visual item in its own <ol> without a
+  // start value, so the parsed slice becomes adjacent one-item lists that all
+  // restart at 1. An explicit continuation value is the same structure with a
+  // better HTML hint. Both forms should become one list in our document model.
+  return rightStart === 1 || rightStart === expectedContinuation;
+}
+
+function repairOrderedListsInFragment(fragment: Fragment): Fragment {
+  const repaired: ProseMirrorNode[] = [];
+
+  fragment.forEach((node) => {
+    const content = node.isLeaf
+      ? node.content
+      : repairOrderedListsInFragment(node.content);
+    const repairedNode = content.eq(node.content) ? node : node.copy(content);
+    const previous = repaired.at(-1);
+
+    if (previous && canJoinOrderedLists(previous, repairedNode)) {
+      repaired[repaired.length - 1] = previous.copy(
+        previous.content.append(repairedNode.content),
+      );
+      return;
+    }
+
+    repaired.push(repairedNode);
+  });
+
+  return Fragment.fromArray(repaired);
+}
+
+function repairFragmentedOrderedLists(slice: Slice): Slice {
+  const content = repairOrderedListsInFragment(slice.content);
+  if (content.eq(slice.content)) return slice;
+  return new Slice(content, slice.openStart, slice.openEnd);
+}
+
 export function createMarkdownPasteExtension() {
   return Extension.create({
     name: "markdownPaste",
@@ -356,7 +416,7 @@ export function createMarkdownPasteExtension() {
         new Plugin({
           key: new PluginKey("markdownPaste"),
           props: {
-            handlePaste(view, event) {
+            handlePaste(view, event, slice) {
               if (!editor.markdown) return false;
               const clipboard = event.clipboardData;
               if (!clipboard) return false;
@@ -371,7 +431,24 @@ export function createMarkdownPasteExtension() {
                 isInsideCodeBlock: $from.parent.type.name === "codeBlock",
               });
 
-              if (mode === "native") return false;
+              if (mode === "native") {
+                // ProseMirror-owned clipboard HTML already represents our exact
+                // document structure. Only repair external rich HTML, where
+                // adjacent <ol> fragments commonly stand for one visual list.
+                if (html && !html.includes("data-pm-slice")) {
+                  const repaired = repairFragmentedOrderedLists(slice);
+                  if (repaired !== slice) {
+                    const tr = view.state.tr
+                      .replaceSelection(repaired)
+                      .scrollIntoView()
+                      .setMeta("paste", true)
+                      .setMeta("uiEvent", "paste");
+                    view.dispatch(tr);
+                    return true;
+                  }
+                }
+                return false;
+              }
 
               if (mode === "literal") {
                 view.dispatch(view.state.tr.insertText(text));
@@ -397,8 +474,8 @@ export function createMarkdownPasteExtension() {
                 return true;
               }
 
-              const slice = Slice.maxOpen(node.content);
-              const tr = view.state.tr.replaceSelection(slice);
+              const parsedSlice = Slice.maxOpen(node.content);
+              const tr = view.state.tr.replaceSelection(parsedSlice);
               view.dispatch(tr);
               return true;
             },