diff --git a/packages/editor/src/extensions/text-direction/__tests__/text-direction.test.ts b/packages/editor/src/extensions/text-direction/__tests__/text-direction.test.ts
new file mode 100644
index 000000000..d0de5a1b0
--- /dev/null
+++ b/packages/editor/src/extensions/text-direction/__tests__/text-direction.test.ts
@@ -0,0 +1,96 @@
+/*
+This file is part of the Notesnook project (https://notesnook.com/)
+
+Copyright (C) 2023 Streetwriters (Private) Limited
+
+This program is free software: you can redistribute it and/or modify
+it under the terms of the GNU General Public License as published by
+the Free Software Foundation, either version 3 of the License, or
+(at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program.  If not, see <http://www.gnu.org/licenses/>.
+*/
+
+import { describe, expect, test } from "vitest";
+import { createEditor } from "../../../../test-utils/index.js";
+import { TaskListNode } from "../../task-list/task-list.js";
+import { TaskItemNode } from "../../task-item/task-item.js";
+import { BulletList } from "../../bullet-list/bullet-list.js";
+import { ListItem } from "../../list-item/list-item.js";
+import { Paragraph } from "../../paragraph/paragraph.js";
+import { TextDirection } from "../text-direction.js";
+
+function directions(editor: {
+  state: { doc: { descendants: (fn: (node: any) => void) => void } };
+}) {
+  const found: Record<string, string[]> = {};
+  editor.state.doc.descendants((node) => {
+    const dir = node.attrs.textDirection;
+    if (dir !== undefined) (found[node.type.name] ??= []).push(dir);
+  });
+  return found;
+}
+
+/** cursor into the first paragraph of the document */
+function cursorInFirstParagraph(editor: any) {
+  let pos = -1;
+  editor.state.doc.descendants((node: any, at: number) => {
+    if (pos === -1 && node.type.name === "paragraph") pos = at + 1;
+  });
+  editor.commands.setTextSelection(pos);
+}
+
+describe("text direction on lists", () => {
+  const cases = [
+    {
+      name: "task list",
+      extensions: {
+        taskList: TaskListNode,
+        taskListItem: TaskItemNode.configure({ nested: true }),
+        paragraph: Paragraph
+      },
+      content: `<ul class="checklist" dir="rtl"><li class="checklist--item"><p dir="rtl">one</p></li><li class="checklist--item"><p dir="rtl">two</p></li></ul>`
+    },
+    {
+      name: "bullet list",
+      extensions: {
+        bulletList: BulletList,
+        listItem: ListItem,
+        paragraph: Paragraph
+      },
+      content: `<ul dir="rtl"><li><p dir="rtl">one</p></li><li><p dir="rtl">two</p></li></ul>`
+    }
+  ];
+
+  for (const { name, extensions, content } of cases) {
+    test(`switching a ${name} to ltr clears the direction of every item`, () => {
+      const { editor } = createEditor({
+        initialContent: content,
+        extensions: {
+          ...extensions,
+          textDirection: TextDirection.configure({
+            types: ["paragraph", "taskList", "bulletList"]
+          })
+        }
+      });
+
+      // every paragraph starts rtl, matching the list
+      const before = directions(editor);
+      expect(Object.values(before).flat()).toContain("rtl");
+
+      cursorInFirstParagraph(editor);
+      editor.commands.setTextDirection(undefined);
+
+      // ...and nothing is left rtl — not the list, not any item, cursor or
+      // not, so the checkboxes/markers and the text no longer disagree
+      const after = directions(editor);
+      expect(Object.values(after).flat()).not.toContain("rtl");
+    });
+  }
+});
diff --git a/packages/editor/src/extensions/text-direction/text-direction.ts b/packages/editor/src/extensions/text-direction/text-direction.ts
index bbc67a1eb..2fda1f74d 100644
--- a/packages/editor/src/extensions/text-direction/text-direction.ts
+++ b/packages/editor/src/extensions/text-direction/text-direction.ts
@@ -114,10 +114,40 @@ export const TextDirection = Extension.create<TextDirectionOptions>({
     return {
       setTextDirection:
         (direction) =>
-        ({ commands }) => {
-          return this.options.types.every((type) =>
-            commands.updateAttributes(type, { textDirection: direction })
-          );
+        ({ state, tr, dispatch }) => {
+          const value = direction || "";
+          const { $from, from, to } = state.selection;
+
+          // Expand to the outermost block that carries a direction, so a
+          // whole task list turns together — every item's paragraph and
+          // all — instead of only the row the cursor is in. Otherwise the
+          // list's own direction flips while its items keep theirs, and the
+          // checkboxes and text end up on opposite sides.
+          let start = from;
+          let end = to;
+          for (let depth = $from.depth; depth > 0; depth--) {
+            if (this.options.types.includes($from.node(depth).type.name)) {
+              start = Math.min(start, $from.before(depth));
+              end = Math.max(end, $from.after(depth));
+            }
+          }
+
+          let changed = false;
+          state.doc.nodesBetween(start, end, (node, pos) => {
+            if (
+              !this.options.types.includes(node.type.name) ||
+              node.attrs.textDirection === value
+            )
+              return;
+            tr.setNodeMarkup(pos, undefined, {
+              ...node.attrs,
+              textDirection: value
+            });
+            changed = true;
+          });
+
+          if (changed) dispatch?.(tr);
+          return changed;
         }
     };
   }