diff --git a/apps/web/src/components/EditorPane.tsx b/apps/web/src/components/EditorPane.tsx
index d5818dda..72b7795e 100644
--- a/apps/web/src/components/EditorPane.tsx
+++ b/apps/web/src/components/EditorPane.tsx
@@ -162,7 +162,13 @@ import { NOTE_HTML_FULL_STYLES } from "@/lib/note-html-export-assets";
 import { downloadNoteHtmlFile, getHtmlImageEmbedNoticeKind } from "@/lib/note-html-export";
 import { openNotePrintPreview, serializeNoteDocumentForPrint } from "@/lib/note-print";
 import type { NoteImageFormat } from "@/lib/note-image-export";
-import { applyPlainTextTab, getAiSlashCommandStart, saveAndSyncEditor, shouldOpenAiFromSpace } from "@/lib/editor-shortcuts";
+import {
+  applyPlainTextTab,
+  getAiSlashCommandStart,
+  preserveEmptyListIndentOnBackspace,
+  saveAndSyncEditor,
+  shouldOpenAiFromSpace,
+} from "@/lib/editor-shortcuts";
 import {
   AI_SPACE_SHORTCUT_CHANGED_EVENT,
   readAiSpaceShortcutPreference,
@@ -1308,6 +1314,11 @@ const RichEditorPane = ({
       handleKeyDown: (view, event) => {
         const { selection } = view.state;
         const currentNode = selection.$from.parent;
+        if (event.key === "Backspace" && preserveEmptyListIndentOnBackspace(view.state, view.dispatch)) {
+          event.preventDefault();
+          return true;
+        }
+
         if (event.key === "Tab" && applyPlainTextTab(view.state, view.dispatch, event.shiftKey)) {
           event.preventDefault();
           return true;
diff --git a/apps/web/src/components/EditorToolbar.tsx b/apps/web/src/components/EditorToolbar.tsx
index 9de5e716..613af869 100644
--- a/apps/web/src/components/EditorToolbar.tsx
+++ b/apps/web/src/components/EditorToolbar.tsx
@@ -25,6 +25,7 @@ import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from "@/comp
 import { formatShortcutBinding, getActiveBlockValue, type ShortcutBinding } from "@/lib/app-helpers";
 import { CODE_BLOCK_LANGUAGES, getCodeBlockLanguageValue } from "@/lib/code-block";
 import { EditorTableMenu } from "@/components/EditorTableMenu";
+import { wrapIndentedParagraphInList } from "@/lib/editor-shortcuts";
 
 const EditorToolbarButton = ({
   active = false,
@@ -113,6 +114,21 @@ const insertMermaidDiagram = (editor: Editor) => {
     .run();
 };
 
+const toggleListAtSelection = (editor: Editor, listType: "bulletList" | "orderedList" | "taskList") => {
+  editor.commands.focus();
+  if (wrapIndentedParagraphInList(editor.state, editor.view.dispatch, listType)) {
+    return;
+  }
+
+  if (listType === "bulletList") {
+    editor.commands.toggleBulletList();
+  } else if (listType === "orderedList") {
+    editor.commands.toggleOrderedList();
+  } else {
+    editor.commands.toggleTaskList();
+  }
+};
+
 export const EditorToolbar = ({
   editor,
   readOnly,
@@ -365,7 +381,7 @@ export const EditorToolbar = ({
             title={`${t("editorToolbar.bulletList")} · ${t("editorToolbar.listIndentHint")}`}
             active={isActive("bulletList")}
             disabled={disabled}
-            onClick={() => run((current) => current.chain().focus().toggleBulletList().run())}
+            onClick={() => run((current) => toggleListAtSelection(current, "bulletList"))}
           >
             <List className="h-4 w-4" />
           </EditorToolbarButton>
@@ -373,7 +389,7 @@ export const EditorToolbar = ({
             title={`${t("editorToolbar.taskList")} · ${t("editorToolbar.listIndentHint")}`}
             active={isActive("taskList")}
             disabled={!canRun((current) => current.can().chain().focus().toggleTaskList().run())}
-            onClick={() => run((current) => current.chain().focus().toggleTaskList().run())}
+            onClick={() => run((current) => toggleListAtSelection(current, "taskList"))}
           >
             <ListTodo className="h-4 w-4" />
           </EditorToolbarButton>
@@ -381,7 +397,7 @@ export const EditorToolbar = ({
             title={`${t("editorToolbar.orderedList")} · ${t("editorToolbar.listIndentHint")}`}
             active={isActive("orderedList")}
             disabled={disabled}
-            onClick={() => run((current) => current.chain().focus().toggleOrderedList().run())}
+            onClick={() => run((current) => toggleListAtSelection(current, "orderedList"))}
           >
             <ListOrdered className="h-4 w-4" />
           </EditorToolbarButton>
diff --git a/apps/web/src/components/MobileStandaloneTiptapEditor.tsx b/apps/web/src/components/MobileStandaloneTiptapEditor.tsx
index 4a0f0b21..5b328c15 100644
--- a/apps/web/src/components/MobileStandaloneTiptapEditor.tsx
+++ b/apps/web/src/components/MobileStandaloneTiptapEditor.tsx
@@ -43,6 +43,7 @@ import {
 } from "@/lib/mobile-editor-standalone";
 import { getMemoUpdateQueueId, isMemoUpdateAlreadyApplied, queueMemoUpdate, shouldQueueMemoSaveError } from "@/lib/sync-queue";
 import { createMarkdownImagePasteRule } from "@/lib/markdown-image-paste";
+import { preserveEmptyListIndentOnBackspace, wrapIndentedParagraphInList } from "@/lib/editor-shortcuts";
 import { ThemeBlock } from "./ThemeBlock";
 import { EditorTagPicker } from "./EditorTagPicker";
 import { listLocalTags } from "@/lib/local-mirror";
@@ -213,6 +214,13 @@ export const MobileStandaloneTiptapEditor = ({
     content: emptyDoc(),
     editorProps: {
       attributes: getMobileEditorInputAttributes("edgeever-mobile-tiptap-content"),
+      handleKeyDown: (view, event) => {
+        if (event.key !== "Backspace" || !preserveEmptyListIndentOnBackspace(view.state, view.dispatch)) {
+          return false;
+        }
+        event.preventDefault();
+        return true;
+      },
     },
     onUpdate: ({ editor: activeEditor }) => {
       contentJsonRef.current = activeEditor.getJSON() as TiptapDoc;
@@ -895,6 +903,7 @@ export const MobileStandaloneTiptapEditor = ({
   const currentNotebookLabel =
     notebookOptions.find((notebook) => notebook.id === memo?.notebookId)?.name ?? t("editor.notebookFallback");
   const activeListItemType = editor?.isActive("taskItem") ? "taskItem" : "listItem";
+  const canWrapIndentedParagraph = Boolean(editor && wrapIndentedParagraphInList(editor.state, undefined));
 
   const fallbackMarkdown = memo ? docToMarkdown(contentJsonRef.current) : "";
   const runEditorCommand = (command: () => boolean) => {
@@ -942,15 +951,21 @@ export const MobileStandaloneTiptapEditor = ({
           boldActive={Boolean(editor?.isActive("bold"))}
           bulletListActive={Boolean(editor?.isActive("bulletList"))}
           taskListActive={Boolean(editor?.isActive("taskList"))}
-          increaseListIndentAvailable={Boolean(editor?.can().chain().focus().sinkListItem(activeListItemType).run())}
+          increaseListIndentAvailable={canWrapIndentedParagraph || Boolean(editor?.can().chain().focus().sinkListItem(activeListItemType).run())}
           decreaseListIndentAvailable={Boolean(editor?.can().chain().focus().liftListItem(activeListItemType).run())}
           blockquoteActive={Boolean(editor?.isActive("blockquote"))}
           locale={locale}
           onPickImage={() => imageInputRef.current?.click()}
           onToggleBold={() => runEditorCommand(() => editor?.chain().focus().toggleBold().run() ?? false)}
-          onToggleBulletList={() => runEditorCommand(() => editor?.chain().focus().toggleBulletList().run() ?? false)}
-          onToggleTaskList={() => runEditorCommand(() => editor?.chain().focus().toggleTaskList().run() ?? false)}
-          onIncreaseListIndent={() => runEditorCommand(() => editor?.chain().focus().sinkListItem(activeListItemType).run() ?? false)}
+          onToggleBulletList={() => runEditorCommand(() => (
+            editor ? wrapIndentedParagraphInList(editor.state, editor.view.dispatch, "bulletList") || editor.commands.toggleBulletList() : false
+          ))}
+          onToggleTaskList={() => runEditorCommand(() => (
+            editor ? wrapIndentedParagraphInList(editor.state, editor.view.dispatch, "taskList") || editor.commands.toggleTaskList() : false
+          ))}
+          onIncreaseListIndent={() => runEditorCommand(() => (
+            editor ? wrapIndentedParagraphInList(editor.state, editor.view.dispatch) || editor.commands.sinkListItem(activeListItemType) : false
+          ))}
           onDecreaseListIndent={() => runEditorCommand(() => editor?.chain().focus().liftListItem(activeListItemType).run() ?? false)}
           onToggleBlockquote={() => runEditorCommand(() => editor?.chain().focus().toggleBlockquote().run() ?? false)}
           onSetHorizontalRule={() => runEditorCommand(() => editor?.chain().focus().setHorizontalRule().run() ?? false)}
diff --git a/apps/web/src/lib/editor-shortcuts.test.mjs b/apps/web/src/lib/editor-shortcuts.test.mjs
index 81e9c69c..13aec368 100644
--- a/apps/web/src/lib/editor-shortcuts.test.mjs
+++ b/apps/web/src/lib/editor-shortcuts.test.mjs
@@ -1,7 +1,14 @@
 import { describe, expect, test } from "bun:test";
 import { EditorState, TextSelection } from "@tiptap/pm/state";
 import { Schema } from "@tiptap/pm/model";
-import { applyPlainTextTab, getAiSlashCommandStart, saveAndSyncEditor, shouldOpenAiFromSpace } from "./editor-shortcuts.ts";
+import {
+  applyPlainTextTab,
+  getAiSlashCommandStart,
+  preserveEmptyListIndentOnBackspace,
+  saveAndSyncEditor,
+  shouldOpenAiFromSpace,
+  wrapIndentedParagraphInList,
+} from "./editor-shortcuts.ts";
 
 const schema = new Schema({
   nodes: {
@@ -29,6 +36,14 @@ const runTab = (state, shiftKey = false) => {
   return { handled, state: nextState };
 };
 
+const runListBackspace = (state) => {
+  let nextState = state;
+  const handled = preserveEmptyListIndentOnBackspace(state, (transaction) => {
+    nextState = state.apply(transaction);
+  });
+  return { handled, state: nextState };
+};
+
 describe("editor shortcut actions", () => {
   test("inserts a tab at the caret in a plain paragraph", () => {
     const result = runTab(createState(["hello world"], 6));
@@ -75,6 +90,82 @@ describe("editor shortcut actions", () => {
     expect(applyPlainTextTab(state, () => {}, false)).toBe(false);
   });
 
+  test("removes an empty sibling list marker while preserving nested indentation", () => {
+    const doc = schema.node("doc", null, [
+      schema.node("bulletList", null, [
+        schema.node("listItem", null, [schema.node("paragraph", null, schema.text("first"))]),
+        schema.node("listItem", null, [schema.node("paragraph")]),
+      ]),
+    ]);
+    const result = runListBackspace(EditorState.create({
+      doc,
+      selection: TextSelection.create(doc, 12),
+    }));
+
+    expect(result.handled).toBe(true);
+    expect(result.state.doc.toJSON()).toEqual({
+      type: "doc",
+      content: [{
+        type: "bulletList",
+        content: [{
+          type: "listItem",
+          content: [
+            { type: "paragraph", content: [{ type: "text", text: "first" }] },
+            { type: "paragraph" },
+          ],
+        }],
+      }],
+    });
+    expect(result.state.selection.$from.parent.type.name).toBe("paragraph");
+    expect(result.state.selection.$from.parent.content.size).toBe(0);
+
+    let nestedListState = result.state;
+    expect(wrapIndentedParagraphInList(result.state, undefined, "bulletList")).toBe(true);
+    expect(wrapIndentedParagraphInList(result.state, (transaction) => {
+      nestedListState = result.state.apply(transaction);
+    }, "bulletList")).toBe(true);
+
+    expect(nestedListState.doc.toJSON()).toEqual({
+      type: "doc",
+      content: [{
+        type: "bulletList",
+        content: [{
+          type: "listItem",
+          content: [
+            { type: "paragraph", content: [{ type: "text", text: "first" }] },
+            {
+              type: "bulletList",
+              content: [{ type: "listItem", content: [{ type: "paragraph" }] }],
+            },
+          ],
+        }],
+      }],
+    });
+  });
+
+  test("keeps the default Backspace behavior outside a removable sibling list item", () => {
+    const firstItemOnly = schema.node("doc", null, [
+      schema.node("bulletList", null, [
+        schema.node("listItem", null, [schema.node("paragraph")]),
+      ]),
+    ]);
+    const nonEmptySecondItem = schema.node("doc", null, [
+      schema.node("bulletList", null, [
+        schema.node("listItem", null, [schema.node("paragraph", null, schema.text("first"))]),
+        schema.node("listItem", null, [schema.node("paragraph", null, schema.text("second"))]),
+      ]),
+    ]);
+
+    expect(preserveEmptyListIndentOnBackspace(
+      EditorState.create({ doc: firstItemOnly, selection: TextSelection.create(firstItemOnly, 3) }),
+      () => {},
+    )).toBe(false);
+    expect(preserveEmptyListIndentOnBackspace(
+      EditorState.create({ doc: nonEmptySecondItem, selection: TextSelection.create(nonEmptySecondItem, 12) }),
+      () => {},
+    )).toBe(false);
+  });
+
   test("recognizes /ai only at a text boundary", () => {
     expect(getAiSlashCommandStart({ caretPosition: 2, insertedText: "i", textBefore: "/a" })).toBe(0);
     expect(getAiSlashCommandStart({ caretPosition: 8, insertedText: "I", textBefore: "hello /a" })).toBe(6);
diff --git a/apps/web/src/lib/editor-shortcuts.ts b/apps/web/src/lib/editor-shortcuts.ts
index d626b7c4..cd9671c9 100644
--- a/apps/web/src/lib/editor-shortcuts.ts
+++ b/apps/web/src/lib/editor-shortcuts.ts
@@ -1,4 +1,5 @@
-import type { EditorState, Transaction } from "@tiptap/pm/state";
+import { TextSelection, type EditorState, type Transaction } from "@tiptap/pm/state";
+import { wrapInList } from "@tiptap/pm/schema-list";
 
 const TAB_DELEGATED_NODE_TYPES = new Set([
   "listItem",
@@ -96,6 +97,113 @@ export const applyPlainTextTab = (
   return true;
 };
 
+/**
+ * Removes the marker from a newly-created empty list item while preserving
+ * its visual/content indentation inside the previous item. Typing a list
+ * marker in the resulting paragraph then creates a nested list, matching
+ * Typora's Backspace workflow.
+ */
+export const preserveEmptyListIndentOnBackspace = (
+  state: EditorState,
+  dispatch: ((transaction: Transaction) => void) | undefined,
+) => {
+  const { selection } = state;
+  if (
+    !selection.empty
+    || selection.$from.parent.type.name !== "paragraph"
+    || selection.$from.parent.content.size !== 0
+    || selection.$from.parentOffset !== 0
+  ) {
+    return false;
+  }
+
+  let listItemDepth = -1;
+  for (let depth = selection.$from.depth - 1; depth > 0; depth -= 1) {
+    const nodeName = selection.$from.node(depth).type.name;
+    if (nodeName === "listItem" || nodeName === "taskItem") {
+      listItemDepth = depth;
+      break;
+    }
+  }
+
+  if (listItemDepth < 1) {
+    return false;
+  }
+
+  const listDepth = listItemDepth - 1;
+  const itemIndex = selection.$from.index(listDepth);
+  const currentItem = selection.$from.node(listItemDepth);
+  const list = selection.$from.node(listDepth);
+  if (
+    itemIndex === 0
+    || currentItem.childCount !== 1
+    || currentItem.firstChild !== selection.$from.parent
+  ) {
+    return false;
+  }
+
+  const previousItem = list.child(itemIndex - 1);
+  if (previousItem.type !== currentItem.type) {
+    return false;
+  }
+
+  if (!dispatch) {
+    return true;
+  }
+
+  const currentItemStart = selection.$from.before(listItemDepth);
+  const previousItemStart = currentItemStart - previousItem.nodeSize;
+  const mergedItem = previousItem.copy(previousItem.content.append(currentItem.content));
+  const transaction = state.tr.replaceWith(
+    previousItemStart,
+    currentItemStart + currentItem.nodeSize,
+    mergedItem,
+  );
+  const paragraphCursor = previousItemStart + previousItem.content.size + 2;
+  transaction.setSelection(TextSelection.create(transaction.doc, paragraphCursor));
+  dispatch(transaction.scrollIntoView());
+  return true;
+};
+
+/**
+ * Turns a direct paragraph below a list item's leading paragraph into a
+ * nested list. This is the structural state produced by the Typora-style
+ * Backspace behavior above.
+ */
+export const wrapIndentedParagraphInList = (
+  state: EditorState,
+  dispatch: ((transaction: Transaction) => void) | undefined,
+  requestedListType?: string,
+) => {
+  const { selection } = state;
+  if (
+    selection.$from.parent.type.name !== "paragraph"
+    || selection.$to.parent !== selection.$from.parent
+  ) {
+    return false;
+  }
+
+  let listItemDepth = -1;
+  for (let depth = selection.$from.depth - 1; depth > 0; depth -= 1) {
+    const nodeName = selection.$from.node(depth).type.name;
+    if (nodeName === "listItem" || nodeName === "taskItem") {
+      listItemDepth = depth;
+      break;
+    }
+  }
+
+  if (
+    listItemDepth < 1
+    || selection.$from.index(listItemDepth) === 0
+  ) {
+    return false;
+  }
+
+  const listTypeName = requestedListType ?? selection.$from.node(listItemDepth - 1).type.name;
+  const listType = state.schema.nodes[listTypeName];
+  return Boolean(listType && wrapInList(listType)(state, dispatch));
+};
+
 export const saveAndSyncEditor = async ({
   hasUnsavedChanges,
   save,