diff --git a/packages/core/src/api/parsers/html/util/__snapshots__/nestedLists.test.ts.snap b/packages/core/src/api/parsers/html/util/__snapshots__/nestedLists.test.ts.snap
index 1db488255b..c35cb364a3 100644
--- a/packages/core/src/api/parsers/html/util/__snapshots__/nestedLists.test.ts.snap
+++ b/packages/core/src/api/parsers/html/util/__snapshots__/nestedLists.test.ts.snap
@@ -1,5 +1,9 @@
 // Vitest Snapshot v1, https://vitest.dev/guide/snapshot.html
 
+exports[`Lift nested lists > Does not merge <li> nodes separated by non-whitespace text 1`] = `"<ul><li>a</li></ul>text<ul><li>b</li></ul>"`;
+
+exports[`Lift nested lists > Leaves <li>s already inside a <ul> alone 1`] = `"<ul><li>existing</li></ul><ul><li>orphan</li></ul>"`;
+
 exports[`Lift nested lists > Lifts multiple bullet lists 1`] = `
 "<ul>
     <div><li>
@@ -142,3 +146,11 @@ exports[`Lift nested lists > Lifts nested numbered lists 1`] = `
     </li>
  </ol>"
 `;
+
+exports[`Lift nested lists > Wraps a single bare <li> in a <ul> 1`] = `"<ul><li>only</li></ul>"`;
+
+exports[`Lift nested lists > Wraps bare <li>s mixed with other top-level content 1`] = `"<p>before</p><ul><li>x</li><li>y</li></ul><p>after</p>"`;
+
+exports[`Lift nested lists > Wraps consecutive bare <li> elements in a <ul> 1`] = `"<ul><li>a</li><li>b</li></ul>"`;
+
+exports[`Lift nested lists > Wraps nested orphan <li>s as inner lists 1`] = `"<ul><li>outer</li><li>inner</li></ul>"`;
diff --git a/packages/core/src/api/parsers/html/util/nestedLists.test.ts b/packages/core/src/api/parsers/html/util/nestedLists.test.ts
index e695efa9c4..aa0bd0a0ce 100644
--- a/packages/core/src/api/parsers/html/util/nestedLists.test.ts
+++ b/packages/core/src/api/parsers/html/util/nestedLists.test.ts
@@ -143,6 +143,36 @@ describe("Lift nested lists", () => {
     await testHTML(html);
   });
 
+  it("Wraps consecutive bare <li> elements in a <ul>", async () => {
+    const html = `<li>a</li><li>b</li>`;
+    await testHTML(html);
+  });
+
+  it("Wraps a single bare <li> in a <ul>", async () => {
+    const html = `<li>only</li>`;
+    await testHTML(html);
+  });
+
+  it("Wraps bare <li>s mixed with other top-level content", async () => {
+    const html = `<p>before</p><li>x</li><li>y</li><p>after</p>`;
+    await testHTML(html);
+  });
+
+  it("Leaves <li>s already inside a <ul> alone", async () => {
+    const html = `<ul><li>existing</li></ul><li>orphan</li>`;
+    await testHTML(html);
+  });
+
+  it("Does not merge <li> nodes separated by non-whitespace text", async () => {
+    const html = `<li>a</li>text<li>b</li>`;
+    await testHTML(html);
+  });
+
+  it("Wraps nested orphan <li>s as inner lists", async () => {
+    const html = `<li>outer<li>inner</li></li>`;
+    await testHTML(html);
+  });
+
   it("Lifts nested mixed lists", async () => {
     const html = `<ol>
     <li>
diff --git a/packages/core/src/api/parsers/html/util/nestedLists.ts b/packages/core/src/api/parsers/html/util/nestedLists.ts
index 9c2427af86..70816fb704 100644
--- a/packages/core/src/api/parsers/html/util/nestedLists.ts
+++ b/packages/core/src/api/parsers/html/util/nestedLists.ts
@@ -6,6 +6,61 @@ function isWhitespaceNode(node: Node) {
   return node.nodeType === 3 && !/\S/.test(node.nodeValue || "");
 }
 
+/**
+ * Step 0, wraps any `<li>` element that is not inside a `<ul>`/`<ol>` in a
+ * fresh `<ul>` so the existing parse rules (which require an `<ul>`/`<ol>`
+ * parent) match. Consecutive orphan `<li>` siblings are grouped under a
+ * single `<ul>`.
+ *
+ * Without this, pasting bare `<li>a</li><li>b</li>` HTML would parse as two
+ * paragraphs because the BulletListItem parse rule only matches `<li>`
+ * whose parent is `<ul>`.
+ */
+function wrapOrphanListItems(element: HTMLElement) {
+  const orphans = Array.from(element.querySelectorAll("li")).filter(
+    (li) => li.closest("ul, ol") === null,
+  );
+  const orphanSet: Set<Element> = new Set(orphans);
+  const handled = new Set<Element>();
+
+  for (const orphan of orphans) {
+    if (handled.has(orphan)) {
+      continue;
+    }
+
+    const group: Element[] = [orphan];
+    handled.add(orphan);
+
+    // Walk siblings via nextSibling (not nextElementSibling) so we can stop
+    // at meaningful text between orphans — only whitespace text is allowed
+    // to bridge two orphan <li>s into the same <ul>.
+    let next: Node | null = orphan.nextSibling;
+    while (next) {
+      if (isWhitespaceNode(next)) {
+        next = next.nextSibling;
+        continue;
+      }
+      if (
+        next.nodeType === 1 &&
+        (next as Element).tagName === "LI" &&
+        orphanSet.has(next as Element)
+      ) {
+        group.push(next as Element);
+        handled.add(next as Element);
+        next = next.nextSibling;
+        continue;
+      }
+      break;
+    }
+
+    const ul = orphan.ownerDocument.createElement("ul");
+    orphan.parentNode!.insertBefore(ul, orphan);
+    for (const li of group) {
+      ul.appendChild(li);
+    }
+  }
+}
+
 /**
  * Step 1, Turns:
  *
@@ -117,6 +172,7 @@ export function nestedListsToBlockNoteStructure(
     element.innerHTML = elementOrHTML;
     elementOrHTML = element;
   }
+  wrapOrphanListItems(elementOrHTML);
   liftNestedListsToParent(elementOrHTML);
   createGroups(elementOrHTML);
   return elementOrHTML;
diff --git a/packages/core/src/editor/transformPasted.test.ts b/packages/core/src/editor/transformPasted.test.ts
new file mode 100644
index 0000000000..9fbb32e9a4
--- /dev/null
+++ b/packages/core/src/editor/transformPasted.test.ts
@@ -0,0 +1,285 @@
+import { TextSelection } from "@tiptap/pm/state";
+import { describe, expect, it } from "vitest";
+
+import { BlockNoteEditor } from "./BlockNoteEditor.js";
+
+/**
+ * @vitest-environment jsdom
+ */
+
+function mountEditor(editor: BlockNoteEditor<any, any, any>) {
+  editor.mount(document.createElement("div"));
+}
+
+function selectStartOfFirstBlock(editor: BlockNoteEditor) {
+  editor.transact((tr) => {
+    let pos: number | undefined;
+    tr.doc.descendants((node, nodePos) => {
+      if (node.type.spec.group === "blockContent") {
+        pos = nodePos + 1;
+        return false;
+      }
+      return pos === undefined;
+    });
+    tr.setSelection(TextSelection.create(tr.doc, pos!));
+  });
+}
+
+describe("paste into empty inline-content block", () => {
+  it.each(["bulletListItem", "numberedListItem", "checkListItem"] as const)(
+    "pastes a paragraph into an empty %s without replacing it",
+    (type) => {
+      const editor = BlockNoteEditor.create({
+        initialContent: [{ type, content: "" }],
+      });
+      mountEditor(editor);
+      selectStartOfFirstBlock(editor);
+
+      editor.pasteHTML(`<p>Pasted</p>`);
+
+      const blocks = editor.document;
+      expect(blocks[0].type).toBe(type);
+      expect(blocks[0].content).toEqual([
+        { type: "text", text: "Pasted", styles: {} },
+      ]);
+    },
+  );
+
+  it("inserts paragraph content into an empty list item without dropping marks", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<p>Hello <strong>world</strong></p>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Hello ", styles: {} },
+      { type: "text", text: "world", styles: { bold: true } },
+    ]);
+  });
+
+  it("merges leading paragraph into empty list item and inserts rest as siblings", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<p>First</p><p>Second</p>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "First", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("paragraph");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "Second", styles: {} },
+    ]);
+  });
+
+  it("replaces an empty list item with a heading when pasting a heading", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<h1>Heading</h1>`);
+
+    // The empty list item is replaced by the heading rather than absorbing
+    // its inline content. Headings carry semantic meaning the user explicitly
+    // chose, so we keep them as-is.
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("heading");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Heading", styles: {} },
+    ]);
+  });
+
+  it("keeps the list item but discards the heading wrapper when a paragraph follows the heading", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    // Heading first means the leading block is not a paragraph, so the
+    // unwrap/retype rule doesn't apply: the empty list item gets replaced
+    // by the pasted heading and the trailing paragraph follows as a sibling.
+    editor.pasteHTML(`<h1>Heading</h1><p>Body</p>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("heading");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Heading", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("paragraph");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "Body", styles: {} },
+    ]);
+  });
+
+  it("still replaces the empty list item when pasting another list item", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<ul><li>Pasted item</li></ul>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    // The empty list item should be replaced (not have inline content
+    // appended in-place), which matches the existing behavior.
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Pasted item", styles: {} },
+    ]);
+  });
+
+  it("pastes a paragraph into a non-empty list item without replacing it", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "abc" }],
+    });
+    mountEditor(editor);
+    editor.setTextCursorPosition(editor.document[0].id, "end");
+
+    editor.pasteHTML(`<p>hello</p>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "abchello", styles: {} },
+    ]);
+  });
+
+  it("pastes bare <li>a</li><li>b</li> into an empty list item as two list items", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<li>a</li><li>b</li>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "a", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("bulletListItem");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "b", styles: {} },
+    ]);
+  });
+
+  it("pastes bare <li>a</li><li>b</li> into a non-empty list item, splicing the first into the cursor", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "X" }],
+    });
+    mountEditor(editor);
+    editor.setTextCursorPosition(editor.document[0].id, "end");
+
+    editor.pasteHTML(`<li>a</li><li>b</li>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Xa", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("bulletListItem");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "b", styles: {} },
+    ]);
+  });
+
+  it("pastes two list items into an empty list item as two siblings", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    editor.pasteHTML(`<ul><li>a</li><li>b</li></ul>`);
+
+    // The empty list item is replaced by the two pasted list items.
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "a", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("bulletListItem");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "b", styles: {} },
+    ]);
+  });
+
+  it("pastes two list items into a non-empty list item, splicing the first into the cursor", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "X" }],
+    });
+    mountEditor(editor);
+    editor.setTextCursorPosition(editor.document[0].id, "end");
+
+    editor.pasteHTML(`<ul><li>a</li><li>b</li></ul>`);
+
+    // The first list item's inline content is spliced at the cursor (the
+    // existing list item becomes "Xa") and the second list item becomes a
+    // new sibling.
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Xa", styles: {} },
+    ]);
+    expect(blocks[1].type).toBe("bulletListItem");
+    expect(blocks[1].content).toEqual([
+      { type: "text", text: "b", styles: {} },
+    ]);
+  });
+
+  it("preserves nested list structure when pasting a nested list into an empty list item", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "bulletListItem", content: "" }],
+    });
+    mountEditor(editor);
+    selectStartOfFirstBlock(editor);
+
+    // Pasting a list with nested children: the leading block is a list item,
+    // so the unwrap/retype rule does not apply and the existing slice-level
+    // list-nesting fix in `transformPasted` keeps the nested structure
+    // intact.
+    editor.pasteHTML(`<ul><li>Outer<ul><li>Inner</li></ul></li></ul>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("bulletListItem");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Outer", styles: {} },
+    ]);
+    expect(blocks[0].children).toHaveLength(1);
+    expect(blocks[0].children[0].type).toBe("bulletListItem");
+    expect(blocks[0].children[0].content).toEqual([
+      { type: "text", text: "Inner", styles: {} },
+    ]);
+  });
+
+  it("preserves the existing paragraph behavior when pasting into a non-empty paragraph", () => {
+    const editor = BlockNoteEditor.create({
+      initialContent: [{ type: "paragraph", content: "Existing " }],
+    });
+    mountEditor(editor);
+    editor.setTextCursorPosition(editor.document[0].id, "end");
+
+    editor.pasteHTML(`<p>added</p>`);
+
+    const blocks = editor.document;
+    expect(blocks[0].type).toBe("paragraph");
+    expect(blocks[0].content).toEqual([
+      { type: "text", text: "Existing added", styles: {} },
+    ]);
+  });
+});
diff --git a/packages/core/src/editor/transformPasted.ts b/packages/core/src/editor/transformPasted.ts
index 2985ad33dc..4f0515df95 100644
--- a/packages/core/src/editor/transformPasted.ts
+++ b/packages/core/src/editor/transformPasted.ts
@@ -113,6 +113,11 @@ export function transformPasted(slice: Slice, view: EditorView) {
   let f = Fragment.from(slice.content);
   f = wrapTableRows(f, view.state.schema);
 
+  const retyped = retypeLeadingParagraphForEmptyTarget(f, view, slice);
+  if (retyped) {
+    return retyped;
+  }
+
   if (isInTableCell(view)) {
     let hasTableContent = false;
     f.descendants((node) => {
@@ -173,6 +178,78 @@ export function transformPasted(slice: Slice, view: EditorView) {
   return new Slice(f, slice.openStart, slice.openEnd);
 }
 
+/**
+ * Pasting plain text into an empty inline-content block (e.g. an empty
+ * bullet list item) would normally replace that block with a paragraph:
+ * BlockNote's serializer always wraps content in
+ * `blockGroup > blockContainer > <block>`, producing a closed slice that
+ * ProseMirror inserts as a new block rather than splicing inline.
+ *
+ * To preserve the empty block's type, retype the leading paragraph in the
+ * slice to match the target block. Subsequent blocks in the slice are left
+ * alone and end up as siblings.
+ *
+ * Scoped to: empty, non-paragraph, inline-content target + paragraph leading
+ * the slice. A non-empty target already gives ProseMirror a valid inline
+ * insertion point so it splices correctly on its own; non-paragraph leading
+ * blocks (heading, list item, …) carry semantic meaning the user picked, so
+ * we keep the existing replace behavior.
+ */
+function retypeLeadingParagraphForEmptyTarget(
+  fragment: Fragment,
+  view: EditorView,
+  slice: Slice,
+): Slice | null {
+  if (isInTableCell(view)) {
+    return null;
+  }
+
+  // `transformPasted` is also called for drop events, where the slice will be
+  // inserted at the drop position rather than the current selection. In that
+  // case the selection-derived target is wrong, so bail out and let the
+  // default behavior handle drops.
+  if (view.dragging) {
+    return null;
+  }
+
+  const blockInfo = getBlockInfoFromSelection(view.state);
+  const target = blockInfo.isBlockContainer
+    ? blockInfo.blockContent.node
+    : null;
+  if (
+    !target ||
+    target.type.name === "paragraph" ||
+    target.type.spec.content !== "inline*" ||
+    target.childCount > 0
+  ) {
+    return null;
+  }
+
+  const blockGroup = fragment.firstChild;
+  const blockContainer = blockGroup?.firstChild;
+  const leading = blockContainer?.firstChild;
+  if (
+    blockGroup?.type.name !== "blockGroup" ||
+    blockContainer?.type.name !== "blockContainer" ||
+    leading?.type.name !== "paragraph"
+  ) {
+    return null;
+  }
+
+  const retyped = target.type.create(target.attrs, leading.content);
+  const newBlockContainer = blockContainer.copy(
+    blockContainer.content.replaceChild(0, retyped),
+  );
+  const newBlockGroup = blockGroup.copy(
+    blockGroup.content.replaceChild(0, newBlockContainer),
+  );
+  return new Slice(
+    fragment.replaceChild(0, newBlockGroup),
+    slice.openStart,
+    slice.openEnd,
+  );
+}
+
 /**
  * Used in `transformPasted` to check if the fix there should be applied, i.e.
  * if the pasted fragment should be wrapped in a `blockContainer` node. This