diff --git a/packages/core/src/blocks/ListItem/BulletListItem/block.ts b/packages/core/src/blocks/ListItem/BulletListItem/block.ts
index 4cd64f5058..0a40bdc1ce 100644
--- a/packages/core/src/blocks/ListItem/BulletListItem/block.ts
+++ b/packages/core/src/blocks/ListItem/BulletListItem/block.ts
@@ -37,17 +37,20 @@ export const createBulletListItemBlockSpec = createBlockSpec(
 
       const parent = element.parentElement;
 
-      if (parent === null) {
-        return undefined;
-      }
-
       if (
+        parent === null ||
         parent.tagName === "UL" ||
         (parent.tagName === "DIV" && parent.parentElement?.tagName === "UL")
       ) {
         return parseDefaultProps(element);
       }
 
+      // Orphan `<li>` (no <ul>/<ol> ancestor) — match as bulletListItem so
+      // pasting bare `<li>` HTML doesn't fall back to a paragraph.
+      if (!element.closest("ul, ol")) {
+        return parseDefaultProps(element);
+      }
+
       return undefined;
     },
     // As `li` elements can contain multiple paragraphs, we need to merge their contents
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
diff --git a/tests/src/unit/core/clipboard/paste/__snapshots__/text/html/pasteHTMLWithMultipleCheckboxesInTableCell.json b/tests/src/unit/core/clipboard/paste/__snapshots__/text/html/pasteHTMLWithMultipleCheckboxesInTableCell.json
index adfce7adf4..e2cf22f640 100644
--- a/tests/src/unit/core/clipboard/paste/__snapshots__/text/html/pasteHTMLWithMultipleCheckboxesInTableCell.json
+++ b/tests/src/unit/core/clipboard/paste/__snapshots__/text/html/pasteHTMLWithMultipleCheckboxesInTableCell.json
@@ -16,8 +16,8 @@
                 {
                   "styles": {},
                   "text": "Cell 1ABC
- Unit tests covering the new feature have been added.
- All existing tests pass.",
+Unit tests covering the new feature have been added.
+All existing tests pass.",
                   "type": "text",
                 },
               ],