From 5bf1c24492acbf2d078495587899d010092b0c4e Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 14:00:14 +0200
Subject: [PATCH 01/26] feat(i18n): add translation keys for ordered list and
 indent/outdent buttons

Adds editor.toggleOrderedList, editor.indentListItem, editor.outdentListItem
and editor.createOrderedList to all 13 translation files.
---
 app/_translations/de.json      | 4 ++++
 app/_translations/en.json      | 4 ++++
 app/_translations/es.json      | 4 ++++
 app/_translations/fr.json      | 4 ++++
 app/_translations/it.json      | 4 ++++
 app/_translations/klingon.json | 4 ++++
 app/_translations/ko.json      | 4 ++++
 app/_translations/nl.json      | 4 ++++
 app/_translations/pirate.json  | 4 ++++
 app/_translations/pl.json      | 4 ++++
 app/_translations/ru.json      | 4 ++++
 app/_translations/tr.json      | 4 ++++
 app/_translations/zh.json      | 4 ++++
 13 files changed, 52 insertions(+)

diff --git a/app/_translations/de.json b/app/_translations/de.json
index 024e2bf6..d8e30c40 100644
--- a/app/_translations/de.json
+++ b/app/_translations/de.json
@@ -1141,6 +1141,9 @@
     "toggleInlineCode": "Code-Formatierung umschalten",
     "toggleHeading2": "Überschrift umschalten",
     "toggleBulletList": "Aufzählungsliste umschalten",
+    "toggleOrderedList": "Nummerierte Liste umschalten",
+    "indentListItem": "Listenelement einrücken",
+    "outdentListItem": "Listenelement ausrücken",
     "toggleBlockquote": "Zitat umschalten",
     "toggleLink": "Verknüpfung einfügen",
     "editImageSize": "Bilgröße ändern",
@@ -1174,6 +1177,7 @@
     "heading2": "Überschrift 2",
     "mediumSectionHeading": "Mittlere Abschnittsüberschrift",
     "createBulletedList": "Aufzählungsliste erstellen",
+    "createOrderedList": "Nummerierte Liste erstellen",
     "taskList": "Aufgabenliste erstellen",
     "createTaskList": "Aufgabenliste erstellen",
     "createCodeBlock": "Code-Block erstellen",
diff --git a/app/_translations/en.json b/app/_translations/en.json
index e4c8ade6..708c69e7 100644
--- a/app/_translations/en.json
+++ b/app/_translations/en.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "Toggle inline code",
     "toggleHeading2": "Toggle heading 2",
     "toggleBulletList": "Toggle bullet list",
+    "toggleOrderedList": "Toggle ordered list",
+    "indentListItem": "Indent list item",
+    "outdentListItem": "Outdent list item",
     "toggleBlockquote": "Toggle blockquote",
     "toggleLink": "Toggle link",
     "editImageSize": "Edit image size",
@@ -1203,6 +1206,7 @@
     "heading2": "Heading 2",
     "mediumSectionHeading": "Medium section heading",
     "createBulletedList": "Create a bulleted list",
+    "createOrderedList": "Create a numbered list",
     "taskList": "Task List",
     "createTaskList": "Create a task list",
     "createCodeBlock": "Create a code block",
diff --git a/app/_translations/es.json b/app/_translations/es.json
index a89a0196..cb7a9853 100644
--- a/app/_translations/es.json
+++ b/app/_translations/es.json
@@ -1145,6 +1145,9 @@
     "toggleInlineCode": "Alternar código en línea",
     "toggleHeading2": "Alternar encabezado 2",
     "toggleBulletList": "Alternar lista con viñetas",
+    "toggleOrderedList": "Alternar lista numerada",
+    "indentListItem": "Sangrar elemento de lista",
+    "outdentListItem": "Quitar sangría del elemento",
     "toggleBlockquote": "Alternar cita",
     "toggleLink": "Alternar enlace",
     "editImageSize": "Editar tamaño de imagen",
@@ -1178,6 +1181,7 @@
     "heading2": "Encabezado 2",
     "mediumSectionHeading": "Encabezado de sección mediana",
     "createBulletedList": "Crear una lista con viñetas",
+    "createOrderedList": "Crear una lista numerada",
     "taskList": "Lista de tareas",
     "createTaskList": "Crear una lista de tareas",
     "createCodeBlock": "Crear un bloque de código",
diff --git a/app/_translations/fr.json b/app/_translations/fr.json
index fd6f0e97..8c9c20bc 100644
--- a/app/_translations/fr.json
+++ b/app/_translations/fr.json
@@ -1145,6 +1145,9 @@
     "toggleInlineCode": "Basculer le code en ligne",
     "toggleHeading2": "Basculer titre 2",
     "toggleBulletList": "Basculer liste à puces",
+    "toggleOrderedList": "Basculer liste numérotée",
+    "indentListItem": "Indenter l'élément de liste",
+    "outdentListItem": "Désindenter l'élément de liste",
     "toggleBlockquote": "Basculer bloc de citation",
     "toggleLink": "Basculer le lien",
     "editImageSize": "Modifier la taille de l’image",
@@ -1178,6 +1181,7 @@
     "heading2": "Titre 2",
     "mediumSectionHeading": "Titre de section moyen",
     "createBulletedList": "Créer une liste à puces",
+    "createOrderedList": "Créer une liste numérotée",
     "taskList": "Liste",
     "createTaskList": "Créer une Liste",
     "createCodeBlock": "Créer un bloc de code",
diff --git a/app/_translations/it.json b/app/_translations/it.json
index 464420d0..287d2004 100644
--- a/app/_translations/it.json
+++ b/app/_translations/it.json
@@ -1145,6 +1145,9 @@
     "toggleInlineCode": "Codice in linea",
     "toggleHeading2": "Intestazione 2",
     "toggleBulletList": "Elenco puntato",
+    "toggleOrderedList": "Elenco numerato",
+    "indentListItem": "Indenta elemento lista",
+    "outdentListItem": "Riduci rientro elemento lista",
     "toggleBlockquote": "Citazione",
     "toggleLink": "Link",
     "editImageSize": "Modifica dimensioni immagine",
@@ -1178,6 +1181,7 @@
     "heading2": "Intestazione 2",
     "mediumSectionHeading": "Intestazione sezione media",
     "createBulletedList": "Crea elenco puntato",
+    "createOrderedList": "Crea elenco numerato",
     "taskList": "Lista Attività",
     "createTaskList": "Crea lista attività",
     "createCodeBlock": "Crea blocco di codice",
diff --git a/app/_translations/klingon.json b/app/_translations/klingon.json
index 6d8cb02f..09416f07 100644
--- a/app/_translations/klingon.json
+++ b/app/_translations/klingon.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "mI' wI' yIchoH",
     "toggleHeading2": "mung 2 yIchoH",
     "toggleBulletList": "mI'be' tetlh yIchoH",
+    "toggleOrderedList": "mI' tetlh yIchoH",
+    "indentListItem": "tetlh gho' yIchoH",
+    "outdentListItem": "tetlh gho' yIchev",
     "toggleBlockquote": "le' tetlh yIchoH",
     "toggleLink": "lI' yIchoH",
     "editImageSize": "nagh beQ 'ab yIchoH",
@@ -1203,6 +1206,7 @@
     "heading2": "mung 2",
     "mediumSectionHeading": "mung motlh",
     "createBulletedList": "mI'be' tetlh yIchenmoH",
+    "createOrderedList": "mI' tetlh yIchenmoH",
     "taskList": "Qu' tetlh",
     "createTaskList": "Qu' tetlh yIchenmoH",
     "createCodeBlock": "mI' wI' yIchenmoH",
diff --git a/app/_translations/ko.json b/app/_translations/ko.json
index 7428daf3..cd12af01 100644
--- a/app/_translations/ko.json
+++ b/app/_translations/ko.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "인라인 코드 전환",
     "toggleHeading2": "제목 2 전환",
     "toggleBulletList": "글머리 기호 목록 전환",
+    "toggleOrderedList": "번호 매기기 목록 전환",
+    "indentListItem": "목록 항목 들여쓰기",
+    "outdentListItem": "목록 항목 내어쓰기",
     "toggleBlockquote": "인용문 전환",
     "toggleLink": "링크 전환",
     "editImageSize": "이미지 크기 편집",
@@ -1203,6 +1206,7 @@
     "heading2": "제목 2",
     "mediumSectionHeading": "중간 섹션 제목",
     "createBulletedList": "글머리 기호 목록 만들기",
+    "createOrderedList": "번호 매기기 목록 만들기",
     "taskList": "작업 목록",
     "createTaskList": "작업 목록 만들기",
     "createCodeBlock": "코드 블록 만들기",
diff --git a/app/_translations/nl.json b/app/_translations/nl.json
index 6f03159b..e5c4fde0 100644
--- a/app/_translations/nl.json
+++ b/app/_translations/nl.json
@@ -1145,6 +1145,9 @@
     "toggleInlineCode": "Inline code wisselen",
     "toggleHeading2": "Kop 2 wisselen",
     "toggleBulletList": "Opsommingslijst wisselen",
+    "toggleOrderedList": "Genummerde lijst wisselen",
+    "indentListItem": "Lijstitem inspringen",
+    "outdentListItem": "Inspringing lijstitem verwijderen",
     "toggleBlockquote": "Citaat wisselen",
     "toggleLink": "Link wisselen",
     "editImageSize": "Afbeeldingsgrootte bewerken",
@@ -1178,6 +1181,7 @@
     "heading2": "Kop 2",
     "mediumSectionHeading": "Middelgrote sectiekop",
     "createBulletedList": "Maak een opsommingslijst",
+    "createOrderedList": "Maak een genummerde lijst",
     "taskList": "Takenlijst",
     "createTaskList": "Maak een takenlijst",
     "createCodeBlock": "Maak een codeblok",
diff --git a/app/_translations/pirate.json b/app/_translations/pirate.json
index fb6836bc..899cbcd7 100644
--- a/app/_translations/pirate.json
+++ b/app/_translations/pirate.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "Cipher",
     "toggleHeading2": "Sub-headline",
     "toggleBulletList": "Shot List",
+    "toggleOrderedList": "Numbered Shot List",
+    "indentListItem": "Walk the Plank Further",
+    "outdentListItem": "Walk the Plank Back",
     "toggleBlockquote": "Parrot",
     "toggleLink": "Rope",
     "editImageSize": "Resize",
@@ -1203,6 +1206,7 @@
     "heading2": "Headline 2",
     "mediumSectionHeading": "Mid Headline",
     "createBulletedList": "Make shot list",
+    "createOrderedList": "Make numbered shot list",
     "taskList": "Duty List",
     "createTaskList": "Make duty list",
     "createCodeBlock": "Make cipher block",
diff --git a/app/_translations/pl.json b/app/_translations/pl.json
index 9ed9e4c5..f4dd4ce3 100644
--- a/app/_translations/pl.json
+++ b/app/_translations/pl.json
@@ -1145,6 +1145,9 @@
     "toggleInlineCode": "Włącz/wyłącz kod w linii",
     "toggleHeading2": "Włącz/wyłącz nagłówek 2",
     "toggleBulletList": "Włącz/wyłącz listę punktowaną",
+    "toggleOrderedList": "Włącz/wyłącz listę numerowaną",
+    "indentListItem": "Wcięcie elementu listy",
+    "outdentListItem": "Usuń wcięcie elementu listy",
     "toggleBlockquote": "Włącz/wyłącz blok cytatu",
     "toggleLink": "Włącz/wyłącz link",
     "editImageSize": "Edytuj rozmiar obrazu",
@@ -1178,6 +1181,7 @@
     "heading2": "Nagłówek 2",
     "mediumSectionHeading": "Średni nagłówek sekcji",
     "createBulletedList": "Utwórz listę punktowaną",
+    "createOrderedList": "Utwórz listę numerowaną",
     "taskList": "Lista zadań",
     "createTaskList": "Utwórz listę zadań",
     "createCodeBlock": "Utwórz blok kodu",
diff --git a/app/_translations/ru.json b/app/_translations/ru.json
index 3f65a211..502eeb26 100644
--- a/app/_translations/ru.json
+++ b/app/_translations/ru.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "Переключить inline-код",
     "toggleHeading2": "Переключить заголовок 2",
     "toggleBulletList": "Переключить маркированный список",
+    "toggleOrderedList": "Переключить нумерованный список",
+    "indentListItem": "Увеличить отступ элемента списка",
+    "outdentListItem": "Уменьшить отступ элемента списка",
     "toggleBlockquote": "Переключить цитату",
     "toggleLink": "Переключить ссылку",
     "editImageSize": "Редактировать размер изображения",
@@ -1203,6 +1206,7 @@
     "heading2": "Заголовок 2",
     "mediumSectionHeading": "Средний заголовок раздела",
     "createBulletedList": "Создать маркированный список",
+    "createOrderedList": "Создать нумерованный список",
     "taskList": "Список задач",
     "createTaskList": "Создать список задач",
     "createCodeBlock": "Создать блок кода",
diff --git a/app/_translations/tr.json b/app/_translations/tr.json
index d85a53ad..e7f147fa 100644
--- a/app/_translations/tr.json
+++ b/app/_translations/tr.json
@@ -1172,6 +1172,9 @@
     "toggleInlineCode": "Satır içi kodu aç/kapat",
     "toggleHeading2": "Başlık 2'yi aç/kapat",
     "toggleBulletList": "Maddeli listeyi aç/kapat",
+    "toggleOrderedList": "Numaralı listeyi aç/kapat",
+    "indentListItem": "Liste öğesini girintile",
+    "outdentListItem": "Liste öğesinin girintisini azalt",
     "toggleBlockquote": "Alıntıyı aç/kapat",
     "toggleLink": "Bağlantıyı aç/kapat",
     "editImageSize": "Görsel boyutunu düzenle",
@@ -1205,6 +1208,7 @@
     "heading2": "Başlık 2",
     "mediumSectionHeading": "Orta bölüm başlığı",
     "createBulletedList": "Maddeli liste oluştur",
+    "createOrderedList": "Numaralı liste oluştur",
     "taskList": "Görev Listesi",
     "createTaskList": "Görev listesi oluştur",
     "createCodeBlock": "Kod bloğu oluştur",
diff --git a/app/_translations/zh.json b/app/_translations/zh.json
index a4f3209b..674295ec 100644
--- a/app/_translations/zh.json
+++ b/app/_translations/zh.json
@@ -1170,6 +1170,9 @@
     "toggleInlineCode": "切换行内代码",
     "toggleHeading2": "切换标题 2",
     "toggleBulletList": "切换无序列表",
+    "toggleOrderedList": "切换有序列表",
+    "indentListItem": "增加列表项缩进",
+    "outdentListItem": "减少列表项缩进",
     "toggleBlockquote": "切换引用块",
     "toggleLink": "切换链接",
     "editImageSize": "编辑图片大小",
@@ -1203,6 +1206,7 @@
     "heading2": "标题 2",
     "mediumSectionHeading": "中节标题",
     "createBulletedList": "创建无序列表",
+    "createOrderedList": "创建有序列表",
     "taskList": "任务列表",
     "createTaskList": "创建任务列表",
     "createCodeBlock": "创建代码块",

From 8d132438b4fad32a94826aefd881f668d5e35135 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 14:00:26 +0200
Subject: [PATCH 02/26] feat(editor): add ordered list, indent and outdent
 toolbar buttons

Adds three buttons after the existing bulletList button:
- orderedList (LeftToRightListNumberIcon, Ctrl+Shift+7, dual-mode aware)
- indent/sinkListItem (TextIndentMoreIcon, disabled when not in a list)
- outdent/liftListItem (TextIndentLessIcon, disabled when not in a list)
---
 .../Parts/TipTap/Toolbar/TipTapToolbar.tsx    | 38 +++++++++++++++++++
 1 file changed, 38 insertions(+)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index de647511..aea4b14a 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -14,6 +14,9 @@ import {
   TextUnderlineIcon,
   Image02Icon,
   LeftToRightListBulletIcon,
+  LeftToRightListNumberIcon,
+  TextIndentMoreIcon,
+  TextIndentLessIcon,
 } from "hugeicons-react";
 import { Button } from "@/app/_components/GlobalComponents/Buttons/Button";
 import { FileModal } from "@/app/_components/GlobalComponents/Modals/FilesModal/FileModal";
@@ -473,6 +476,41 @@ export const TiptapToolbar = ({
           >
             <LeftToRightListBulletIcon className="h-4 w-4" />
           </Button>
+          {/* fccview is onto you! */}
+          <Button
+            variant={editor && editor.isActive("orderedList") ? "secondary" : "ghost"}
+            size="sm"
+            onMouseDown={(e) => e.preventDefault()}
+            onClick={() =>
+              handleDualModeButton(
+                () => editor.chain().focus().toggleOrderedList().run(),
+                MarkdownUtils.insertOrderedList
+              )
+            }
+            title={`${t('editor.toggleOrderedList')} (${mod}+Shift+7)`}
+          >
+            <LeftToRightListNumberIcon className="h-4 w-4" />
+          </Button>
+          <Button
+            variant="ghost"
+            size="sm"
+            onMouseDown={(e) => e.preventDefault()}
+            onClick={() => editor?.chain().focus().sinkListItem('listItem').run()}
+            disabled={!editor || !editor.can().sinkListItem('listItem')}
+            title={t('editor.indentListItem')}
+          >
+            <TextIndentMoreIcon className="h-4 w-4" />
+          </Button>
+          <Button
+            variant="ghost"
+            size="sm"
+            onMouseDown={(e) => e.preventDefault()}
+            onClick={() => editor?.chain().focus().liftListItem('listItem').run()}
+            disabled={!editor || !editor.can().liftListItem('listItem')}
+            title={t('editor.outdentListItem')}
+          >
+            <TextIndentLessIcon className="h-4 w-4" />
+          </Button>
           <Button
             variant={editor && editor.isActive("blockquote") ? "secondary" : "ghost"}
             size="sm"

From cf3c132ce84597bc885d52265d71d740e6d42822 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 14:00:34 +0200
Subject: [PATCH 03/26] feat(editor): add ordered list entry to slash commands
 menu

Inserts an orderedList item directly after bulletList in the slash command
list, using LeftToRightListNumberIcon and the existing toggleOrderedList command.
---
 .../Parts/TipTap/CustomExtensions/SlashCommands.tsx    | 10 ++++++++++
 1 file changed, 10 insertions(+)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
index 0d65e360..68e94e42 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
@@ -6,6 +6,7 @@ import {
   Heading01Icon,
   Heading02Icon,
   LeftToRightListBulletIcon,
+  LeftToRightListNumberIcon,
   CheckmarkSquare04Icon,
   SourceCodeIcon,
   QuoteUpIcon,
@@ -75,6 +76,15 @@ const getSlashCommands = (t: (key: string) => string): SlashCommandItem[] => [
       editor.chain().focus().deleteRange(range).toggleBulletList().run();
     },
   },
+  // fccview is onto you!
+  {
+    title: t("editor.orderedList"),
+    description: t("editor.createOrderedList"),
+    icon: <LeftToRightListNumberIcon className="h-4 w-4" />,
+    command: ({ editor, range }) => {
+      editor.chain().focus().deleteRange(range).toggleOrderedList().run();
+    },
+  },
   {
     title: t("editor.taskList"),
     description: t("editor.createTaskList"),

From 67b8ec41b93bb97e81e0d742824dad9900fa1cf8 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 16:33:54 +0200
Subject: [PATCH 04/26] fix(editor): correct indent/outdent button disabled
 logic

- Indent: was disabled for first list item (can().sinkListItem returns false
  without a previous sibling). Changed to isActive('listItem') so the button
  stays visible; clicking on an unsinkable item is a no-op but less confusing
  than a grayed-out button.
- Outdent: was enabled on top-level list items, causing liftListItem to remove
  the list entirely on click. Added a ProseMirror depth check so outdent is
  only enabled when the item is nested (grandgrandparent node is a listItem).
---
 .../Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx      | 11 +++++++++--
 1 file changed, 9 insertions(+), 2 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index aea4b14a..b03fd0d1 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -496,7 +496,7 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() => editor?.chain().focus().sinkListItem('listItem').run()}
-            disabled={!editor || !editor.can().sinkListItem('listItem')}
+            disabled={!editor || !editor.isActive('listItem')}
             title={t('editor.indentListItem')}
           >
             <TextIndentMoreIcon className="h-4 w-4" />
@@ -506,7 +506,14 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() => editor?.chain().focus().liftListItem('listItem').run()}
-            disabled={!editor || !editor.can().liftListItem('listItem')}
+            disabled={
+              !editor ||
+              !editor.isActive('listItem') ||
+              // fccview is onto you!
+              editor.state.selection.$anchor.node(
+                editor.state.selection.$anchor.depth - 3
+              )?.type.name !== 'listItem'
+            }
             title={t('editor.outdentListItem')}
           >
             <TextIndentLessIcon className="h-4 w-4" />

From 9d6eb70810475ed03359011bf1cf6e0c2289288b Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 16:50:59 +0200
Subject: [PATCH 05/26] fix(editor): fix ordered list toggle and indent/outdent
 disabled state

- Ordered list button: bypass handleButtonClick wrapper for rich-text mode.
  The wrapper saved/restored cursor positions (from/to) around the command,
  but toggleOrderedList changes document structure so the saved positions
  become stale, causing the next click to land outside the list and create
  a new one instead of toggling. Now calls chain().focus() directly.
- Indent disabled: changed from isActive('listItem') (checks current block
  type = paragraph, always false) to isActive('bulletList')||isActive('orderedList').
- Outdent disabled: same reliable list-active check, depth condition unchanged.
---
 .../Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx      | 11 +++++------
 1 file changed, 5 insertions(+), 6 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index b03fd0d1..8e3dd9a8 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -482,10 +482,9 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() =>
-              handleDualModeButton(
-                () => editor.chain().focus().toggleOrderedList().run(),
-                MarkdownUtils.insertOrderedList
-              )
+              isMarkdownMode
+                ? handleMarkdownButtonClick(MarkdownUtils.insertOrderedList)
+                : editor.chain().focus().toggleOrderedList().run()
             }
             title={`${t('editor.toggleOrderedList')} (${mod}+Shift+7)`}
           >
@@ -496,7 +495,7 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() => editor?.chain().focus().sinkListItem('listItem').run()}
-            disabled={!editor || !editor.isActive('listItem')}
+            disabled={!editor || (!editor.isActive('bulletList') && !editor.isActive('orderedList'))}
             title={t('editor.indentListItem')}
           >
             <TextIndentMoreIcon className="h-4 w-4" />
@@ -508,7 +507,7 @@ export const TiptapToolbar = ({
             onClick={() => editor?.chain().focus().liftListItem('listItem').run()}
             disabled={
               !editor ||
-              !editor.isActive('listItem') ||
+              (!editor.isActive('bulletList') && !editor.isActive('orderedList')) ||
               // fccview is onto you!
               editor.state.selection.$anchor.node(
                 editor.state.selection.$anchor.depth - 3

From fd0813665c5be83d184ac8124c2eb82d679265f2 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 16:52:17 +0200
Subject: [PATCH 06/26] fix(editor): add explicit Tab/Shift-Tab handling for
 list indentation

TipTap's built-in ListItem Tab handler wasn't reliably firing after the
custom extension returned false. Now explicitly:
- Tab in ordered/bullet list: sinkListItem (indent), event always consumed
  to prevent browser focus-jump even if the item has no previous sibling.
- Shift-Tab in list: liftListItem only when nested (depth check); at level 1
  the event is consumed but the list is preserved.
---
 .../TipTap/CustomExtensions/KeyboardShortcuts.tsx   | 13 +++++++++++++
 1 file changed, 13 insertions(+)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
index 4466fcf4..19d45085 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
@@ -53,12 +53,25 @@ export const KeyboardShortcuts = Extension.create<KeyboardShortcutsOptions>({
         if (this.editor.isActive("table")) {
           return this.editor.chain().focus().goToNextCell().run();
         }
+        // fccview is onto you!
+        if (this.editor.isActive("orderedList") || this.editor.isActive("bulletList")) {
+          this.editor.chain().focus().sinkListItem("listItem").run();
+          return true;
+        }
         return false;
       },
       "Shift-Tab": () => {
         if (this.editor.isActive("table")) {
           return this.editor.chain().focus().goToPreviousCell().run();
         }
+        if (this.editor.isActive("orderedList") || this.editor.isActive("bulletList")) {
+          const { $anchor } = this.editor.state.selection;
+          const isNested = $anchor.node($anchor.depth - 3)?.type.name === "listItem";
+          if (isNested) {
+            return this.editor.chain().focus().liftListItem("listItem").run();
+          }
+          return true;
+        }
         return false;
       },
       "Mod-r": () => {

From 8c6117df3e14f1824088309e14444e742b026e7f Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 17:38:32 +0200
Subject: [PATCH 07/26] fix(editor): reactive list state, robust toggle and
 depth check
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

- Import useEditorState (TipTap v3) to subscribe to selection changes;
  the toolbar now re-renders when the cursor moves in/out of a list, fixing
  the stale disabled state on mouse-click and arrow-key navigation.
- Selector computes isInList, isNested (ancestor traversal, no fixed depth
  offset), isInOrderedList, and currentItemIsEmpty — all driven by the
  live editor state.
- Ordered list toggle: when already in an ordered list with an empty item,
  use liftListItem instead of toggleOrderedList, which avoids the "cursor
  jumps / extra 1. inserted" bug that occurs on empty paragraphs.
- Outdent disabled: replaced editor.state.selection.$anchor.node(depth-3)
  fixed-offset heuristic with a proper ancestor walk through listItem nodes,
  which works correctly regardless of document nesting depth.
---
 .../Parts/TipTap/Toolbar/TipTapToolbar.tsx    | 54 +++++++++++++------
 1 file changed, 38 insertions(+), 16 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index 8e3dd9a8..b10ac471 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -1,4 +1,4 @@
-import { Editor } from "@tiptap/react";
+import { Editor, useEditorState } from "@tiptap/react";
 import {
   TextBoldIcon,
   TextItalicIcon,
@@ -103,6 +103,29 @@ export const TiptapToolbar = ({
     }
   }, [linkRequestPending, linkRequestHasSelection, isMarkdownMode, editor, onLinkRequestHandled]);
 
+  // fccview is onto you!
+  const listState = useEditorState({
+    editor,
+    selector: ({ editor: e }) => {
+      if (!e) return { isInList: false, isNested: false, isInOrderedList: false, currentItemIsEmpty: false };
+      const isInOrderedList = e.isActive('orderedList');
+      const isInList = e.isActive('bulletList') || isInOrderedList;
+      let isNested = false;
+      if (isInList) {
+        const { $anchor } = e.state.selection;
+        outer: for (let d = $anchor.depth; d >= 0; d--) {
+          if ($anchor.node(d).type.name === 'listItem') {
+            for (let d2 = d - 1; d2 >= 0; d2--) {
+              if ($anchor.node(d2).type.name === 'listItem') { isNested = true; break outer; }
+            }
+            break;
+          }
+        }
+      }
+      return { isInList, isNested, isInOrderedList, currentItemIsEmpty: e.state.selection.$anchor.parent.textContent === '' };
+    },
+  }) ?? { isInList: false, isNested: false, isInOrderedList: false, currentItemIsEmpty: false };
+
   if (!editor) {
     return null;
   }
@@ -478,14 +501,20 @@ export const TiptapToolbar = ({
           </Button>
           {/* fccview is onto you! */}
           <Button
-            variant={editor && editor.isActive("orderedList") ? "secondary" : "ghost"}
+            variant={listState.isInOrderedList ? "secondary" : "ghost"}
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
-            onClick={() =>
-              isMarkdownMode
-                ? handleMarkdownButtonClick(MarkdownUtils.insertOrderedList)
-                : editor.chain().focus().toggleOrderedList().run()
-            }
+            onClick={() => {
+              if (isMarkdownMode) {
+                handleMarkdownButtonClick(MarkdownUtils.insertOrderedList);
+                return;
+              }
+              if (listState.isInOrderedList && listState.currentItemIsEmpty) {
+                editor.chain().focus().liftListItem('listItem').run();
+              } else {
+                editor.chain().focus().toggleOrderedList().run();
+              }
+            }}
             title={`${t('editor.toggleOrderedList')} (${mod}+Shift+7)`}
           >
             <LeftToRightListNumberIcon className="h-4 w-4" />
@@ -495,7 +524,7 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() => editor?.chain().focus().sinkListItem('listItem').run()}
-            disabled={!editor || (!editor.isActive('bulletList') && !editor.isActive('orderedList'))}
+            disabled={!listState.isInList}
             title={t('editor.indentListItem')}
           >
             <TextIndentMoreIcon className="h-4 w-4" />
@@ -505,14 +534,7 @@ export const TiptapToolbar = ({
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
             onClick={() => editor?.chain().focus().liftListItem('listItem').run()}
-            disabled={
-              !editor ||
-              (!editor.isActive('bulletList') && !editor.isActive('orderedList')) ||
-              // fccview is onto you!
-              editor.state.selection.$anchor.node(
-                editor.state.selection.$anchor.depth - 3
-              )?.type.name !== 'listItem'
-            }
+            disabled={!listState.isInList || !listState.isNested}
             title={t('editor.outdentListItem')}
           >
             <TextIndentLessIcon className="h-4 w-4" />

From 544345c5dd1f7cf03463d31b7727951a7280334e Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 18:46:05 +0200
Subject: [PATCH 08/26] fix(editor): apply same empty-item toggle fix to bullet
 list button

Same root cause as the ordered list fix: toggleBulletList on an empty list
item caused cursor jumps or extra bullet symbols. Now uses liftListItem when
the current item is empty, consistent with the ordered list behaviour.
Also adds isInBulletList to the useEditorState selector so the button's
active variant is driven by reactive state rather than a stale isActive call.
---
 .../Parts/TipTap/Toolbar/TipTapToolbar.tsx    | 29 ++++++++++++-------
 1 file changed, 18 insertions(+), 11 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index b10ac471..6bb70406 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -107,9 +107,10 @@ export const TiptapToolbar = ({
   const listState = useEditorState({
     editor,
     selector: ({ editor: e }) => {
-      if (!e) return { isInList: false, isNested: false, isInOrderedList: false, currentItemIsEmpty: false };
+      if (!e) return { isInList: false, isNested: false, isInBulletList: false, isInOrderedList: false, currentItemIsEmpty: false };
+      const isInBulletList = e.isActive('bulletList');
       const isInOrderedList = e.isActive('orderedList');
-      const isInList = e.isActive('bulletList') || isInOrderedList;
+      const isInList = isInBulletList || isInOrderedList;
       let isNested = false;
       if (isInList) {
         const { $anchor } = e.state.selection;
@@ -122,9 +123,9 @@ export const TiptapToolbar = ({
           }
         }
       }
-      return { isInList, isNested, isInOrderedList, currentItemIsEmpty: e.state.selection.$anchor.parent.textContent === '' };
+      return { isInList, isNested, isInBulletList, isInOrderedList, currentItemIsEmpty: e.state.selection.$anchor.parent.textContent === '' };
     },
-  }) ?? { isInList: false, isNested: false, isInOrderedList: false, currentItemIsEmpty: false };
+  }) ?? { isInList: false, isNested: false, isInBulletList: false, isInOrderedList: false, currentItemIsEmpty: false };
 
   if (!editor) {
     return null;
@@ -486,15 +487,21 @@ export const TiptapToolbar = ({
             <Heading02Icon className="h-4 w-4" />
           </Button>
           <Button
-            variant={editor && editor.isActive("bulletList") ? "secondary" : "ghost"}
+            variant={listState.isInBulletList ? "secondary" : "ghost"}
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
-            onClick={() =>
-              handleDualModeButton(
-                () => editor.chain().focus().toggleBulletList().run(),
-                MarkdownUtils.insertBulletList
-              )
-            }
+            onClick={() => {
+              if (isMarkdownMode) {
+                handleMarkdownButtonClick(MarkdownUtils.insertBulletList);
+                return;
+              }
+              // fccview is onto you!
+              if (listState.isInBulletList && listState.currentItemIsEmpty) {
+                editor.chain().focus().liftListItem('listItem').run();
+              } else {
+                editor.chain().focus().toggleBulletList().run();
+              }
+            }}
             title={`${t('editor.toggleBulletList')} (${mod}+Shift+8)`}
           >
             <LeftToRightListBulletIcon className="h-4 w-4" />

From 4dd25fabb3f64d7c56e554224e7f62491cbf2c5c Mon Sep 17 00:00:00 2001
From: Nikolai Andree <nikolai.andree@datagroup.de>
Date: Mon, 11 May 2026 19:00:13 +0200
Subject: [PATCH 09/26] chore(editor): remove stray comments

---
 .../Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx  | 1 -
 .../Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx      | 1 -
 .../Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx               | 3 ---
 3 files changed, 5 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
index 19d45085..66040208 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/KeyboardShortcuts.tsx
@@ -53,7 +53,6 @@ export const KeyboardShortcuts = Extension.create<KeyboardShortcutsOptions>({
         if (this.editor.isActive("table")) {
           return this.editor.chain().focus().goToNextCell().run();
         }
-        // fccview is onto you!
         if (this.editor.isActive("orderedList") || this.editor.isActive("bulletList")) {
           this.editor.chain().focus().sinkListItem("listItem").run();
           return true;
diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
index 68e94e42..4baf4aea 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/CustomExtensions/SlashCommands.tsx
@@ -76,7 +76,6 @@ const getSlashCommands = (t: (key: string) => string): SlashCommandItem[] => [
       editor.chain().focus().deleteRange(range).toggleBulletList().run();
     },
   },
-  // fccview is onto you!
   {
     title: t("editor.orderedList"),
     description: t("editor.createOrderedList"),
diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index 6bb70406..dd66c675 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -103,7 +103,6 @@ export const TiptapToolbar = ({
     }
   }, [linkRequestPending, linkRequestHasSelection, isMarkdownMode, editor, onLinkRequestHandled]);
 
-  // fccview is onto you!
   const listState = useEditorState({
     editor,
     selector: ({ editor: e }) => {
@@ -495,7 +494,6 @@ export const TiptapToolbar = ({
                 handleMarkdownButtonClick(MarkdownUtils.insertBulletList);
                 return;
               }
-              // fccview is onto you!
               if (listState.isInBulletList && listState.currentItemIsEmpty) {
                 editor.chain().focus().liftListItem('listItem').run();
               } else {
@@ -506,7 +504,6 @@ export const TiptapToolbar = ({
           >
             <LeftToRightListBulletIcon className="h-4 w-4" />
           </Button>
-          {/* fccview is onto you! */}
           <Button
             variant={listState.isInOrderedList ? "secondary" : "ghost"}
             size="sm"

From 9554d2ba0d57a14fac2ec88bef93a0c443862539 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:25:47 +0200
Subject: [PATCH 10/26] fix(editor): align MD bullet/ordered list markers to
 Turndown convention
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Turndown serialises bullet items as '-   ' (dash + 3 spaces) and ordered
items as 'N.  ' (number + dot + 2 spaces), placing text at column 4.
The insertBulletList and insertOrderedList helpers used single-space
variants, causing visual inconsistency after a RT→MD roundtrip.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 8 ++++----
 1 file changed, 4 insertions(+), 4 deletions(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index 6b23a833..1f8d5b9a 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -190,16 +190,16 @@ const processLineSelection = (
 export const insertBulletList = (textarea: HTMLTextAreaElement): string =>
   processLineSelection(textarea, /^-\s/, (line, _, allMatch) => {
     if (line.trim() === "") return line;
-    return allMatch ? line.replace(/^-\s/, "") : `- ${line}`;
+    return allMatch ? line.replace(/^-\s+/, "") : `-   ${line}`;
   });
 
 export const insertOrderedList = (textarea: HTMLTextAreaElement): string => {
   let num = 1;
   return processLineSelection(textarea, /^\d+\.\s/, (line, _, allMatch) => {
     if (line.trim() === "") return line;
-    if (allMatch) return line.replace(/^\d+\.\s/, "");
-    const clean = line.replace(/^\d+\.\s/, "");
-    return `${num++}. ${clean}`;
+    if (allMatch) return line.replace(/^\d+\.\s+/, "");
+    const clean = line.replace(/^\d+\.\s+/, "");
+    return `${num++}.  ${clean}`;
   });
 };
 

From 357ef25e4eaddaac87e06fcde1a736aa1054c2cf Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:26:59 +0200
Subject: [PATCH 11/26] feat(editor): add ordered list continuation on Enter in
 MD mode

Pressing Enter on a numbered list line ('1. text') now inserts a new
line with the incremented number and same spacing ('2.  '). Pressing
Enter on an empty numbered item ('1.  ') removes the marker, consistent
with bullet list behaviour.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/SyntaxHighlightedEditor.tsx  |  4 +++-
 app/_utils/markdown-editor-utils.ts           | 21 +++++++++++++++++++
 2 files changed, 24 insertions(+), 1 deletion(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/SyntaxHighlightedEditor.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/SyntaxHighlightedEditor.tsx
index 5d197004..cd894457 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/SyntaxHighlightedEditor.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/SyntaxHighlightedEditor.tsx
@@ -135,7 +135,9 @@ export const SyntaxHighlightedEditor = ({
       e.preventDefault();
       onLinkRequest?.(textarea.selectionStart !== textarea.selectionEnd);
     } else if (e.key === "Enter" && !isMod && !e.shiftKey && !e.altKey) {
-      const newContent = MarkdownUtils.handleBulletListEnter(textarea);
+      const newContent =
+        MarkdownUtils.handleBulletListEnter(textarea) ??
+        MarkdownUtils.handleOrderedListEnter(textarea);
       if (newContent !== null) {
         e.preventDefault();
         const { scrollTop, scrollLeft, selectionStart, selectionEnd } =
diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index 1f8d5b9a..c4689dd4 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -356,6 +356,27 @@ export const handleBulletListEnter = (
   return insertTextAtCursor(textarea, "\n" + bullet, "", "", 0);
 };
 
+export const handleOrderedListEnter = (
+  textarea: HTMLTextAreaElement
+): string | null => {
+  const { start } = getTextareaSelection(textarea);
+  const { lineContent, lineStart } = _getLineAtPosition(textarea.value, start);
+
+  const match = lineContent.match(/^(\d+)\.(\s+)(.*)/);
+  if (!match) return null;
+
+  const [, numStr, spacing, content] = match;
+  if (!content.trim()) {
+    const newVal =
+      textarea.value.substring(0, lineStart) +
+      textarea.value.substring(lineStart + lineContent.length);
+    return _updateEditor(textarea, newVal, lineStart, lineStart);
+  }
+
+  const nextNum = parseInt(numStr, 10) + 1;
+  return insertTextAtCursor(textarea, `\n${nextNum}.${spacing}`, "", "", 0);
+};
+
 export const autolinkPastedContent = (
   textarea: HTMLTextAreaElement,
   pasted: string

From 24ae169bf43ae0eeb052730a83381238fdc0751c Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:28:07 +0200
Subject: [PATCH 12/26] feat(editor): add indentLines/outdentLines helpers for
 MD mode
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Adds two text-based helpers in markdown-editor-utils that operate on all
selected lines (or the cursor line when nothing is selected).
indentLines prepends 4 spaces; outdentLines removes the first 4 spaces
if present, otherwise leaves the line unchanged — consistent with the
library's Shift+Tab outdent behaviour.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 10 ++++++++++
 1 file changed, 10 insertions(+)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index c4689dd4..bead67c8 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -356,6 +356,16 @@ export const handleBulletListEnter = (
   return insertTextAtCursor(textarea, "\n" + bullet, "", "", 0);
 };
 
+export const indentLines = (textarea: HTMLTextAreaElement): string =>
+  processLineSelection(textarea, /^/, (line) =>
+    line.trim() === "" ? line : "    " + line
+  );
+
+export const outdentLines = (textarea: HTMLTextAreaElement): string =>
+  processLineSelection(textarea, /^ {4}/, (line) =>
+    line.startsWith("    ") ? line.slice(4) : line
+  );
+
 export const handleOrderedListEnter = (
   textarea: HTMLTextAreaElement
 ): string | null => {

From c444cefef71978180ae10d96d1412f626670da62 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:28:37 +0200
Subject: [PATCH 13/26] fix(editor): wire indent/outdent buttons for MD mode,
 fix disabled state

Indent and outdent buttons now route to the text-based indentLines/
outdentLines helpers in MD mode instead of calling TipTap commands that
have no effect there. The disabled condition is also corrected: buttons
are always enabled in MD mode (outdent on a line with <4 spaces is a
no-op, consistent with Shift+Tab).

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/TipTapToolbar.tsx    | 20 +++++++++++++++----
 1 file changed, 16 insertions(+), 4 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index dd66c675..50733a6d 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -527,8 +527,14 @@ export const TiptapToolbar = ({
             variant="ghost"
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
-            onClick={() => editor?.chain().focus().sinkListItem('listItem').run()}
-            disabled={!listState.isInList}
+            onClick={() => {
+              if (isMarkdownMode) {
+                handleMarkdownButtonClick(MarkdownUtils.indentLines);
+                return;
+              }
+              editor?.chain().focus().sinkListItem('listItem').run();
+            }}
+            disabled={!isMarkdownMode && !listState.isInList}
             title={t('editor.indentListItem')}
           >
             <TextIndentMoreIcon className="h-4 w-4" />
@@ -537,8 +543,14 @@ export const TiptapToolbar = ({
             variant="ghost"
             size="sm"
             onMouseDown={(e) => e.preventDefault()}
-            onClick={() => editor?.chain().focus().liftListItem('listItem').run()}
-            disabled={!listState.isInList || !listState.isNested}
+            onClick={() => {
+              if (isMarkdownMode) {
+                handleMarkdownButtonClick(MarkdownUtils.outdentLines);
+                return;
+              }
+              editor?.chain().focus().liftListItem('listItem').run();
+            }}
+            disabled={!isMarkdownMode && (!listState.isInList || !listState.isNested)}
             title={t('editor.outdentListItem')}
           >
             <TextIndentLessIcon className="h-4 w-4" />

From f5596ca2df87a47781a436a43e41e97d65fc6d09 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:39:15 +0200
Subject: [PATCH 14/26] feat(i18n): add editor.listOptions translation key in
 all 13 locales

New key for the list menu dropdown trigger button label, added to
en, de, es, fr, it, ko, nl, pl, ru, tr, zh, klingon, and pirate.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_translations/de.json      | 1 +
 app/_translations/en.json      | 1 +
 app/_translations/es.json      | 1 +
 app/_translations/fr.json      | 1 +
 app/_translations/it.json      | 1 +
 app/_translations/klingon.json | 1 +
 app/_translations/ko.json      | 1 +
 app/_translations/nl.json      | 1 +
 app/_translations/pirate.json  | 1 +
 app/_translations/pl.json      | 1 +
 app/_translations/ru.json      | 1 +
 app/_translations/tr.json      | 1 +
 app/_translations/zh.json      | 1 +
 13 files changed, 13 insertions(+)

diff --git a/app/_translations/de.json b/app/_translations/de.json
index d8e30c40..b3289636 100644
--- a/app/_translations/de.json
+++ b/app/_translations/de.json
@@ -1140,6 +1140,7 @@
     "toggleStrikethrough": "Durchstreichung umschalten",
     "toggleInlineCode": "Code-Formatierung umschalten",
     "toggleHeading2": "Überschrift umschalten",
+    "listOptions": "Liste",
     "toggleBulletList": "Aufzählungsliste umschalten",
     "toggleOrderedList": "Nummerierte Liste umschalten",
     "indentListItem": "Listenelement einrücken",
diff --git a/app/_translations/en.json b/app/_translations/en.json
index 708c69e7..9f0e55f6 100644
--- a/app/_translations/en.json
+++ b/app/_translations/en.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "Toggle strikethrough",
     "toggleInlineCode": "Toggle inline code",
     "toggleHeading2": "Toggle heading 2",
+    "listOptions": "List",
     "toggleBulletList": "Toggle bullet list",
     "toggleOrderedList": "Toggle ordered list",
     "indentListItem": "Indent list item",
diff --git a/app/_translations/es.json b/app/_translations/es.json
index cb7a9853..0bb4ff81 100644
--- a/app/_translations/es.json
+++ b/app/_translations/es.json
@@ -1144,6 +1144,7 @@
     "toggleStrikethrough": "Alternar tachado",
     "toggleInlineCode": "Alternar código en línea",
     "toggleHeading2": "Alternar encabezado 2",
+    "listOptions": "Lista",
     "toggleBulletList": "Alternar lista con viñetas",
     "toggleOrderedList": "Alternar lista numerada",
     "indentListItem": "Sangrar elemento de lista",
diff --git a/app/_translations/fr.json b/app/_translations/fr.json
index 8c9c20bc..f9b9ee08 100644
--- a/app/_translations/fr.json
+++ b/app/_translations/fr.json
@@ -1144,6 +1144,7 @@
     "toggleStrikethrough": "Basculer le barré",
     "toggleInlineCode": "Basculer le code en ligne",
     "toggleHeading2": "Basculer titre 2",
+    "listOptions": "Liste",
     "toggleBulletList": "Basculer liste à puces",
     "toggleOrderedList": "Basculer liste numérotée",
     "indentListItem": "Indenter l'élément de liste",
diff --git a/app/_translations/it.json b/app/_translations/it.json
index 287d2004..f7b31d05 100644
--- a/app/_translations/it.json
+++ b/app/_translations/it.json
@@ -1144,6 +1144,7 @@
     "toggleStrikethrough": "Barrato",
     "toggleInlineCode": "Codice in linea",
     "toggleHeading2": "Intestazione 2",
+    "listOptions": "Lista",
     "toggleBulletList": "Elenco puntato",
     "toggleOrderedList": "Elenco numerato",
     "indentListItem": "Indenta elemento lista",
diff --git a/app/_translations/klingon.json b/app/_translations/klingon.json
index 09416f07..24c2beab 100644
--- a/app/_translations/klingon.json
+++ b/app/_translations/klingon.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "Qaw' tlhegh yIchoH",
     "toggleInlineCode": "mI' wI' yIchoH",
     "toggleHeading2": "mung 2 yIchoH",
+    "listOptions": "tetlh",
     "toggleBulletList": "mI'be' tetlh yIchoH",
     "toggleOrderedList": "mI' tetlh yIchoH",
     "indentListItem": "tetlh gho' yIchoH",
diff --git a/app/_translations/ko.json b/app/_translations/ko.json
index cd12af01..20d39267 100644
--- a/app/_translations/ko.json
+++ b/app/_translations/ko.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "취소선 전환",
     "toggleInlineCode": "인라인 코드 전환",
     "toggleHeading2": "제목 2 전환",
+    "listOptions": "목록",
     "toggleBulletList": "글머리 기호 목록 전환",
     "toggleOrderedList": "번호 매기기 목록 전환",
     "indentListItem": "목록 항목 들여쓰기",
diff --git a/app/_translations/nl.json b/app/_translations/nl.json
index e5c4fde0..c5925aff 100644
--- a/app/_translations/nl.json
+++ b/app/_translations/nl.json
@@ -1144,6 +1144,7 @@
     "toggleStrikethrough": "Doorhalen wisselen",
     "toggleInlineCode": "Inline code wisselen",
     "toggleHeading2": "Kop 2 wisselen",
+    "listOptions": "Lijst",
     "toggleBulletList": "Opsommingslijst wisselen",
     "toggleOrderedList": "Genummerde lijst wisselen",
     "indentListItem": "Lijstitem inspringen",
diff --git a/app/_translations/pirate.json b/app/_translations/pirate.json
index 899cbcd7..5af5dec5 100644
--- a/app/_translations/pirate.json
+++ b/app/_translations/pirate.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "Strike",
     "toggleInlineCode": "Cipher",
     "toggleHeading2": "Sub-headline",
+    "listOptions": "Loot Menu",
     "toggleBulletList": "Shot List",
     "toggleOrderedList": "Numbered Shot List",
     "indentListItem": "Walk the Plank Further",
diff --git a/app/_translations/pl.json b/app/_translations/pl.json
index f4dd4ce3..678c110f 100644
--- a/app/_translations/pl.json
+++ b/app/_translations/pl.json
@@ -1144,6 +1144,7 @@
     "toggleStrikethrough": "Włącz/wyłącz przekreślenie",
     "toggleInlineCode": "Włącz/wyłącz kod w linii",
     "toggleHeading2": "Włącz/wyłącz nagłówek 2",
+    "listOptions": "Lista",
     "toggleBulletList": "Włącz/wyłącz listę punktowaną",
     "toggleOrderedList": "Włącz/wyłącz listę numerowaną",
     "indentListItem": "Wcięcie elementu listy",
diff --git a/app/_translations/ru.json b/app/_translations/ru.json
index 502eeb26..1d6228c0 100644
--- a/app/_translations/ru.json
+++ b/app/_translations/ru.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "Переключить зачёркивание",
     "toggleInlineCode": "Переключить inline-код",
     "toggleHeading2": "Переключить заголовок 2",
+    "listOptions": "Список",
     "toggleBulletList": "Переключить маркированный список",
     "toggleOrderedList": "Переключить нумерованный список",
     "indentListItem": "Увеличить отступ элемента списка",
diff --git a/app/_translations/tr.json b/app/_translations/tr.json
index e7f147fa..b52edf70 100644
--- a/app/_translations/tr.json
+++ b/app/_translations/tr.json
@@ -1171,6 +1171,7 @@
     "toggleStrikethrough": "Üstü çizili yap/kaldır",
     "toggleInlineCode": "Satır içi kodu aç/kapat",
     "toggleHeading2": "Başlık 2'yi aç/kapat",
+    "listOptions": "Liste",
     "toggleBulletList": "Maddeli listeyi aç/kapat",
     "toggleOrderedList": "Numaralı listeyi aç/kapat",
     "indentListItem": "Liste öğesini girintile",
diff --git a/app/_translations/zh.json b/app/_translations/zh.json
index 674295ec..c6155c1a 100644
--- a/app/_translations/zh.json
+++ b/app/_translations/zh.json
@@ -1169,6 +1169,7 @@
     "toggleStrikethrough": "切换删除线",
     "toggleInlineCode": "切换行内代码",
     "toggleHeading2": "切换标题 2",
+    "listOptions": "列表",
     "toggleBulletList": "切换无序列表",
     "toggleOrderedList": "切换有序列表",
     "indentListItem": "增加列表项缩进",

From 42630518a5c472bc0742d28739c571295b9a99f9 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Tue, 12 May 2026 18:39:21 +0200
Subject: [PATCH 15/26] feat(editor): replace four list buttons with
 ListMenuDropdown

Bullet list, ordered list, indent and outdent are now grouped under a
single dropdown in the toolbar, following the same pattern as
CodeBlocksDropdown. The dropdown handles both rich-text (TipTap
commands) and MD mode (text-based helpers), and shows an active state
when the cursor is inside a list in rich-text mode.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx | 160 ++++++++++++++++++
 .../Parts/TipTap/Toolbar/TipTapToolbar.tsx    |  81 +--------
 2 files changed, 167 insertions(+), 74 deletions(-)
 create mode 100644 app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
new file mode 100644
index 00000000..0304d2b6
--- /dev/null
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -0,0 +1,160 @@
+"use client";
+
+import { Editor } from "@tiptap/react";
+import {
+  ArrowDown01Icon,
+  LeftToRightListBulletIcon,
+  LeftToRightListNumberIcon,
+  TextIndentMoreIcon,
+  TextIndentLessIcon,
+} from "hugeicons-react";
+import { Button } from "@/app/_components/GlobalComponents/Buttons/Button";
+import { ToolbarDropdown } from "./ToolbarDropdown";
+import { useTranslations } from "next-intl";
+import * as MarkdownUtils from "@/app/_utils/markdown-editor-utils";
+
+interface ListMenuDropdownProps {
+  editor: Editor | null;
+  isMarkdownMode: boolean;
+  onMarkdownChange?: (content: string) => void;
+  listState: {
+    isInList: boolean;
+    isNested: boolean;
+    isInBulletList: boolean;
+    isInOrderedList: boolean;
+    currentItemIsEmpty: boolean;
+  };
+}
+
+export const ListMenuDropdown = ({
+  editor,
+  isMarkdownMode,
+  onMarkdownChange,
+  listState,
+}: ListMenuDropdownProps) => {
+  const t = useTranslations();
+
+  if (!editor) return null;
+
+  const applyMarkdown = (fn: (ta: HTMLTextAreaElement) => string) => {
+    const textarea = document.getElementById(
+      "markdown-editor-textarea"
+    ) as HTMLTextAreaElement;
+    if (textarea && onMarkdownChange) {
+      const scrollTop = textarea.scrollTop;
+      const scrollLeft = textarea.scrollLeft;
+      const newContent = fn(textarea);
+      const selectionStart = textarea.selectionStart;
+      const selectionEnd = textarea.selectionEnd;
+      onMarkdownChange(newContent);
+      requestAnimationFrame(() => {
+        const ta = document.getElementById(
+          "markdown-editor-textarea"
+        ) as HTMLTextAreaElement;
+        if (ta) {
+          ta.focus({ preventScroll: true });
+          ta.setSelectionRange(selectionStart, selectionEnd);
+          ta.scrollTop = scrollTop;
+          ta.scrollLeft = scrollLeft;
+        }
+      });
+    }
+  };
+
+  const handleBulletList = () => {
+    if (isMarkdownMode) {
+      applyMarkdown(MarkdownUtils.insertBulletList);
+      return;
+    }
+    if (listState.isInBulletList && listState.currentItemIsEmpty) {
+      editor.chain().focus().liftListItem("listItem").run();
+    } else {
+      editor.chain().focus().toggleBulletList().run();
+    }
+  };
+
+  const handleOrderedList = () => {
+    if (isMarkdownMode) {
+      applyMarkdown(MarkdownUtils.insertOrderedList);
+      return;
+    }
+    if (listState.isInOrderedList && listState.currentItemIsEmpty) {
+      editor.chain().focus().liftListItem("listItem").run();
+    } else {
+      editor.chain().focus().toggleOrderedList().run();
+    }
+  };
+
+  const handleIndent = () => {
+    if (isMarkdownMode) {
+      applyMarkdown(MarkdownUtils.indentLines);
+      return;
+    }
+    editor.chain().focus().sinkListItem("listItem").run();
+  };
+
+  const handleOutdent = () => {
+    if (isMarkdownMode) {
+      applyMarkdown(MarkdownUtils.outdentLines);
+      return;
+    }
+    editor.chain().focus().liftListItem("listItem").run();
+  };
+
+  const isActive = listState.isInList;
+
+  const trigger = (
+    <Button
+      variant={isActive ? "secondary" : "ghost"}
+      size="sm"
+      onMouseDown={(e) => e.preventDefault()}
+      className="flex items-center gap-1"
+      title={t("editor.listOptions")}
+    >
+      <LeftToRightListBulletIcon className="h-4 w-4" />
+      <ArrowDown01Icon className="h-3 w-3" />
+    </Button>
+  );
+
+  return (
+    <ToolbarDropdown trigger={trigger}>
+      <div className="py-1">
+        <button
+          className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm"
+          onMouseDown={(e) => e.preventDefault()}
+          onClick={handleBulletList}
+        >
+          <LeftToRightListBulletIcon className="h-4 w-4 shrink-0" />
+          <span>{t("editor.toggleBulletList")}</span>
+        </button>
+        <button
+          className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm"
+          onMouseDown={(e) => e.preventDefault()}
+          onClick={handleOrderedList}
+        >
+          <LeftToRightListNumberIcon className="h-4 w-4 shrink-0" />
+          <span>{t("editor.toggleOrderedList")}</span>
+        </button>
+        <div className="my-1 border-t border-border" />
+        <button
+          className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm disabled:opacity-50 disabled:cursor-not-allowed"
+          onMouseDown={(e) => e.preventDefault()}
+          onClick={handleIndent}
+          disabled={!isMarkdownMode && !listState.isInList}
+        >
+          <TextIndentMoreIcon className="h-4 w-4 shrink-0" />
+          <span>{t("editor.indentListItem")}</span>
+        </button>
+        <button
+          className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm disabled:opacity-50 disabled:cursor-not-allowed"
+          onMouseDown={(e) => e.preventDefault()}
+          onClick={handleOutdent}
+          disabled={!isMarkdownMode && (!listState.isInList || !listState.isNested)}
+        >
+          <TextIndentLessIcon className="h-4 w-4 shrink-0" />
+          <span>{t("editor.outdentListItem")}</span>
+        </button>
+      </div>
+    </ToolbarDropdown>
+  );
+};
diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
index 50733a6d..4cc654a2 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/TipTapToolbar.tsx
@@ -13,16 +13,13 @@ import {
   Tv02Icon,
   TextUnderlineIcon,
   Image02Icon,
-  LeftToRightListBulletIcon,
-  LeftToRightListNumberIcon,
-  TextIndentMoreIcon,
-  TextIndentLessIcon,
 } from "hugeicons-react";
 import { Button } from "@/app/_components/GlobalComponents/Buttons/Button";
 import { FileModal } from "@/app/_components/GlobalComponents/Modals/FilesModal/FileModal";
 import { ImageSizeModal } from "@/app/_components/GlobalComponents/Modals/ImageSizeModal";
 import { CodeBlockDropdown } from "@/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/CodeBlocksDropdown";
 import { DiagramsDropdown } from "@/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/DiagramsDropdown";
+import { ListMenuDropdown } from "@/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown";
 import { TableInsertModal } from "@/app/_components/FeatureComponents/Notes/Parts/Table/TableInsertModal";
 import { FontFamilyDropdown } from "@/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/FontFamilyDropdown";
 import { useState, useEffect } from "react";
@@ -485,76 +482,12 @@ export const TiptapToolbar = ({
           >
             <Heading02Icon className="h-4 w-4" />
           </Button>
-          <Button
-            variant={listState.isInBulletList ? "secondary" : "ghost"}
-            size="sm"
-            onMouseDown={(e) => e.preventDefault()}
-            onClick={() => {
-              if (isMarkdownMode) {
-                handleMarkdownButtonClick(MarkdownUtils.insertBulletList);
-                return;
-              }
-              if (listState.isInBulletList && listState.currentItemIsEmpty) {
-                editor.chain().focus().liftListItem('listItem').run();
-              } else {
-                editor.chain().focus().toggleBulletList().run();
-              }
-            }}
-            title={`${t('editor.toggleBulletList')} (${mod}+Shift+8)`}
-          >
-            <LeftToRightListBulletIcon className="h-4 w-4" />
-          </Button>
-          <Button
-            variant={listState.isInOrderedList ? "secondary" : "ghost"}
-            size="sm"
-            onMouseDown={(e) => e.preventDefault()}
-            onClick={() => {
-              if (isMarkdownMode) {
-                handleMarkdownButtonClick(MarkdownUtils.insertOrderedList);
-                return;
-              }
-              if (listState.isInOrderedList && listState.currentItemIsEmpty) {
-                editor.chain().focus().liftListItem('listItem').run();
-              } else {
-                editor.chain().focus().toggleOrderedList().run();
-              }
-            }}
-            title={`${t('editor.toggleOrderedList')} (${mod}+Shift+7)`}
-          >
-            <LeftToRightListNumberIcon className="h-4 w-4" />
-          </Button>
-          <Button
-            variant="ghost"
-            size="sm"
-            onMouseDown={(e) => e.preventDefault()}
-            onClick={() => {
-              if (isMarkdownMode) {
-                handleMarkdownButtonClick(MarkdownUtils.indentLines);
-                return;
-              }
-              editor?.chain().focus().sinkListItem('listItem').run();
-            }}
-            disabled={!isMarkdownMode && !listState.isInList}
-            title={t('editor.indentListItem')}
-          >
-            <TextIndentMoreIcon className="h-4 w-4" />
-          </Button>
-          <Button
-            variant="ghost"
-            size="sm"
-            onMouseDown={(e) => e.preventDefault()}
-            onClick={() => {
-              if (isMarkdownMode) {
-                handleMarkdownButtonClick(MarkdownUtils.outdentLines);
-                return;
-              }
-              editor?.chain().focus().liftListItem('listItem').run();
-            }}
-            disabled={!isMarkdownMode && (!listState.isInList || !listState.isNested)}
-            title={t('editor.outdentListItem')}
-          >
-            <TextIndentLessIcon className="h-4 w-4" />
-          </Button>
+          <ListMenuDropdown
+            editor={editor}
+            isMarkdownMode={isMarkdownMode}
+            onMarkdownChange={onMarkdownChange}
+            listState={listState}
+          />
           <Button
             variant={editor && editor.isActive("blockquote") ? "secondary" : "ghost"}
             size="sm"

From 1c60db63842ef4bc90368372ae034fc33cbe01d2 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Wed, 13 May 2026 18:29:27 +0200
Subject: [PATCH 16/26] fix(editor): handle indented list items in Enter
 continuation (MD mode)

handleBulletListEnter and handleOrderedListEnter matched only at the
line start, so pressing Enter on a nested/indented item (e.g.
'    -   sub') inserted a plain newline instead of continuing the list.
Regex now captures leading whitespace and includes it in the new line
prefix so all indent levels work correctly.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 12 ++++++------
 1 file changed, 6 insertions(+), 6 deletions(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index bead67c8..1424721a 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -342,10 +342,10 @@ export const handleBulletListEnter = (
   const { start } = getTextareaSelection(textarea);
   const { lineContent, lineStart } = _getLineAtPosition(textarea.value, start);
 
-  const match = lineContent.match(/^(-\s+)(.*)/);
+  const match = lineContent.match(/^(\s*)(-\s+)(.*)/);
   if (!match) return null;
 
-  const [, bullet, content] = match;
+  const [, indent, bullet, content] = match;
   if (!content.trim()) {
     const newVal =
       textarea.value.substring(0, lineStart) +
@@ -353,7 +353,7 @@ export const handleBulletListEnter = (
     return _updateEditor(textarea, newVal, lineStart, lineStart);
   }
 
-  return insertTextAtCursor(textarea, "\n" + bullet, "", "", 0);
+  return insertTextAtCursor(textarea, "\n" + indent + bullet, "", "", 0);
 };
 
 export const indentLines = (textarea: HTMLTextAreaElement): string =>
@@ -372,10 +372,10 @@ export const handleOrderedListEnter = (
   const { start } = getTextareaSelection(textarea);
   const { lineContent, lineStart } = _getLineAtPosition(textarea.value, start);
 
-  const match = lineContent.match(/^(\d+)\.(\s+)(.*)/);
+  const match = lineContent.match(/^(\s*)(\d+)\.(\s+)(.*)/);
   if (!match) return null;
 
-  const [, numStr, spacing, content] = match;
+  const [, indent, numStr, spacing, content] = match;
   if (!content.trim()) {
     const newVal =
       textarea.value.substring(0, lineStart) +
@@ -384,7 +384,7 @@ export const handleOrderedListEnter = (
   }
 
   const nextNum = parseInt(numStr, 10) + 1;
-  return insertTextAtCursor(textarea, `\n${nextNum}.${spacing}`, "", "", 0);
+  return insertTextAtCursor(textarea, `\n${indent}${nextNum}.${spacing}`, "", "", 0);
 };
 
 export const autolinkPastedContent = (

From e345848401914d079ef039ac99f1135634c74444 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Wed, 13 May 2026 18:29:32 +0200
Subject: [PATCH 17/26] fix(editor): use can() checks for indent/outdent
 disabled state in RT mode
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Replaced isInList/isNested with reactive editor.can().sinkListItem() and
editor.can().liftListItem() calls so the dropdown items are disabled
precisely when TipTap cannot execute the command — e.g. indent is now
correctly disabled on the first item of a list.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx    | 16 +++++++++++++---
 1 file changed, 13 insertions(+), 3 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
index 0304d2b6..367d83b7 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -1,6 +1,6 @@
 "use client";
 
-import { Editor } from "@tiptap/react";
+import { Editor, useEditorState } from "@tiptap/react";
 import {
   ArrowDown01Icon,
   LeftToRightListBulletIcon,
@@ -34,6 +34,16 @@ export const ListMenuDropdown = ({
 }: ListMenuDropdownProps) => {
   const t = useTranslations();
 
+  const canSink = useEditorState({
+    editor,
+    selector: ({ editor: e }) => (e ? e.can().sinkListItem("listItem") : false),
+  }) ?? false;
+
+  const canLift = useEditorState({
+    editor,
+    selector: ({ editor: e }) => (e ? e.can().liftListItem("listItem") : false),
+  }) ?? false;
+
   if (!editor) return null;
 
   const applyMarkdown = (fn: (ta: HTMLTextAreaElement) => string) => {
@@ -140,7 +150,7 @@ export const ListMenuDropdown = ({
           className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm disabled:opacity-50 disabled:cursor-not-allowed"
           onMouseDown={(e) => e.preventDefault()}
           onClick={handleIndent}
-          disabled={!isMarkdownMode && !listState.isInList}
+          disabled={!isMarkdownMode && !canSink}
         >
           <TextIndentMoreIcon className="h-4 w-4 shrink-0" />
           <span>{t("editor.indentListItem")}</span>
@@ -149,7 +159,7 @@ export const ListMenuDropdown = ({
           className="w-full flex items-center gap-2 px-3 py-1.5 text-left hover:bg-accent text-sm disabled:opacity-50 disabled:cursor-not-allowed"
           onMouseDown={(e) => e.preventDefault()}
           onClick={handleOutdent}
-          disabled={!isMarkdownMode && (!listState.isInList || !listState.isNested)}
+          disabled={!isMarkdownMode && !canLift}
         >
           <TextIndentLessIcon className="h-4 w-4 shrink-0" />
           <span>{t("editor.outdentListItem")}</span>

From 92e609edf662d29a5ce28882e8d903225f2b9123 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Wed, 13 May 2026 18:45:02 +0200
Subject: [PATCH 18/26] fix(editor): renumber ordered list items on indent, fix
 RT roundtrip
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

remark does not reliably parse nested ordered lists starting at numbers
other than 1 (a CommonMark edge case where the 'cannot interrupt
paragraph' rule is over-applied). To ensure the MD→RT roundtrip is
always correct, indentLines now renumbers ordered list items in the
selection starting from 1 when they are indented. Each contiguous group
of ordered items gets its own counter that resets at blank lines and
non-ordered lines.

Also fixes the RT indent disabled state: uses editor.can().sinkListItem
and editor.can().liftListItem so the dropdown items reflect the exact
command availability, e.g. indent is disabled on the first item of a
list level.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 23 +++++++++++++++++++----
 1 file changed, 19 insertions(+), 4 deletions(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index 1424721a..d5dcc1de 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -356,10 +356,25 @@ export const handleBulletListEnter = (
   return insertTextAtCursor(textarea, "\n" + indent + bullet, "", "", 0);
 };
 
-export const indentLines = (textarea: HTMLTextAreaElement): string =>
-  processLineSelection(textarea, /^/, (line) =>
-    line.trim() === "" ? line : "    " + line
-  );
+export const indentLines = (textarea: HTMLTextAreaElement): string => {
+  let orderedCounter = 1;
+  let lastWasOrdered = false;
+  return processLineSelection(textarea, /^/, (line) => {
+    if (line.trim() === "") {
+      lastWasOrdered = false;
+      return line;
+    }
+    const orderedMatch = line.match(/^(\s*)(\d+)\.\s+(.*)/);
+    if (orderedMatch) {
+      if (!lastWasOrdered) orderedCounter = 1;
+      const [, indent, , content] = orderedMatch;
+      lastWasOrdered = true;
+      return `    ${indent}${orderedCounter++}.  ${content}`;
+    }
+    lastWasOrdered = false;
+    return "    " + line;
+  });
+};
 
 export const outdentLines = (textarea: HTMLTextAreaElement): string =>
   processLineSelection(textarea, /^ {4}/, (line) =>

From 6de0f88c936c9ab7965c8358f97aa6c4f65a5e7a Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 10:14:38 +0200
Subject: [PATCH 19/26] fix(editor): empty line gets list marker on toggle-on,
 collapse cursor after indent

Two fixes in markdown-editor-utils:

1. insertBulletList / insertOrderedList now add list markers to empty
   lines when toggling on, so clicking the list button on a blank line
   produces a list item. When toggling off (allMatch), empty lines are
   left unchanged as before.

2. indentLines / outdentLines collapse the selection to a cursor after
   the operation. processLineSelection selected the full modified block
   which caused the next keystroke to delete all indented content.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 21 ++++++++++++++-------
 1 file changed, 14 insertions(+), 7 deletions(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index d5dcc1de..b72ff4dc 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -189,15 +189,15 @@ const processLineSelection = (
 
 export const insertBulletList = (textarea: HTMLTextAreaElement): string =>
   processLineSelection(textarea, /^-\s/, (line, _, allMatch) => {
-    if (line.trim() === "") return line;
-    return allMatch ? line.replace(/^-\s+/, "") : `-   ${line}`;
+    if (allMatch) return line.trim() === "" ? line : line.replace(/^-\s+/, "");
+    return line.trim() === "" ? "-   " : `-   ${line}`;
   });
 
 export const insertOrderedList = (textarea: HTMLTextAreaElement): string => {
   let num = 1;
   return processLineSelection(textarea, /^\d+\.\s/, (line, _, allMatch) => {
-    if (line.trim() === "") return line;
-    if (allMatch) return line.replace(/^\d+\.\s+/, "");
+    if (allMatch) return line.trim() === "" ? line : line.replace(/^\d+\.\s+/, "");
+    if (line.trim() === "") return `${num++}.  `;
     const clean = line.replace(/^\d+\.\s+/, "");
     return `${num++}.  ${clean}`;
   });
@@ -359,7 +359,7 @@ export const handleBulletListEnter = (
 export const indentLines = (textarea: HTMLTextAreaElement): string => {
   let orderedCounter = 1;
   let lastWasOrdered = false;
-  return processLineSelection(textarea, /^/, (line) => {
+  const result = processLineSelection(textarea, /^/, (line) => {
     if (line.trim() === "") {
       lastWasOrdered = false;
       return line;
@@ -374,12 +374,19 @@ export const indentLines = (textarea: HTMLTextAreaElement): string => {
     lastWasOrdered = false;
     return "    " + line;
   });
+  const pos = textarea.selectionEnd;
+  textarea.setSelectionRange(pos, pos);
+  return result;
 };
 
-export const outdentLines = (textarea: HTMLTextAreaElement): string =>
-  processLineSelection(textarea, /^ {4}/, (line) =>
+export const outdentLines = (textarea: HTMLTextAreaElement): string => {
+  const result = processLineSelection(textarea, /^ {4}/, (line) =>
     line.startsWith("    ") ? line.slice(4) : line
   );
+  const pos = textarea.selectionEnd;
+  textarea.setSelectionRange(pos, pos);
+  return result;
+};
 
 export const handleOrderedListEnter = (
   textarea: HTMLTextAreaElement

From 320106d9dda9a2ca933991e05d4a52f748010c13 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 10:30:41 +0200
Subject: [PATCH 20/26] fix(editor): ordered list button now works on empty
 lines in MD mode

processLineSelection treated empty lines as 'matching' the pattern so
an all-empty selection produced allMatch=true, sending the callback into
toggle-off mode instead of toggle-on. Added a hasNonEmpty guard so
allMatch is only true when at least one non-empty line actually matches.

Result: clicking the ordered list button (or bullet list) on a blank
line now inserts a list marker, consistent with non-empty lines.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 3 ++-
 1 file changed, 2 insertions(+), 1 deletion(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index b72ff4dc..73318262 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -170,7 +170,8 @@ const processLineSelection = (
   const { lineEnd } = _getLineAtPosition(value, end);
   const lines = value.substring(lineStart, lineEnd).split("\n");
 
-  const allMatch = lines.every((l) => pattern.test(l) || l.trim() === "");
+  const hasNonEmpty = lines.some((l) => l.trim() !== "");
+  const allMatch = hasNonEmpty && lines.every((l) => pattern.test(l) || l.trim() === "");
   const newLines = lines.map((line, i) => processFn(line, i, allMatch));
   const newContent = newLines.join("\n");
   const newValue =

From 7dea9ffe8b4f00cb9b52deb53e307925261eed55 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 10:57:56 +0200
Subject: [PATCH 21/26] fix(editor): exit all list levels when toggling list in
 RT mode
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Add liftOutOfList() loop in ListMenuDropdown that repeatedly calls
liftListItem until the cursor is no longer inside any list, instead of
lifting only one level. Also enables cross-type switching (bullet ↔
ordered) without first exiting the list.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx | 24 +++++++++++++++----
 1 file changed, 20 insertions(+), 4 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
index 367d83b7..3e899053 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -71,13 +71,26 @@ export const ListMenuDropdown = ({
     }
   };
 
+  const liftOutOfList = () => {
+    let safety = 20;
+    while (
+      safety-- > 0 &&
+      (editor.isActive("bulletList") || editor.isActive("orderedList"))
+    ) {
+      if (!editor.chain().focus().liftListItem("listItem").run()) break;
+    }
+  };
+
   const handleBulletList = () => {
     if (isMarkdownMode) {
       applyMarkdown(MarkdownUtils.insertBulletList);
       return;
     }
-    if (listState.isInBulletList && listState.currentItemIsEmpty) {
-      editor.chain().focus().liftListItem("listItem").run();
+    if (listState.isInBulletList) {
+      liftOutOfList();
+    } else if (listState.isInOrderedList) {
+      liftOutOfList();
+      editor.chain().focus().toggleBulletList().run();
     } else {
       editor.chain().focus().toggleBulletList().run();
     }
@@ -88,8 +101,11 @@ export const ListMenuDropdown = ({
       applyMarkdown(MarkdownUtils.insertOrderedList);
       return;
     }
-    if (listState.isInOrderedList && listState.currentItemIsEmpty) {
-      editor.chain().focus().liftListItem("listItem").run();
+    if (listState.isInOrderedList) {
+      liftOutOfList();
+    } else if (listState.isInBulletList) {
+      liftOutOfList();
+      editor.chain().focus().toggleOrderedList().run();
     } else {
       editor.chain().focus().toggleOrderedList().run();
     }

From 3b2afd980c5f312fa22ed970dda376d58bf7e33a Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 10:58:01 +0200
Subject: [PATCH 22/26] fix(editor): make MD list toggle buttons indent-aware
 and support type switching

Rewrite insertBulletList and insertOrderedList to use /^\s*-\s/ and
/^\s*\d+\.\s/ patterns so indented list items are recognized. When all
selected lines are already a list of the other type, convert markers
instead of stacking a new marker on top.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-editor-utils.ts | 89 ++++++++++++++++++++++++++---
 1 file changed, 81 insertions(+), 8 deletions(-)

diff --git a/app/_utils/markdown-editor-utils.ts b/app/_utils/markdown-editor-utils.ts
index 73318262..2e0369b8 100644
--- a/app/_utils/markdown-editor-utils.ts
+++ b/app/_utils/markdown-editor-utils.ts
@@ -188,20 +188,93 @@ const processLineSelection = (
   return newValue;
 };
 
-export const insertBulletList = (textarea: HTMLTextAreaElement): string =>
-  processLineSelection(textarea, /^-\s/, (line, _, allMatch) => {
-    if (allMatch) return line.trim() === "" ? line : line.replace(/^-\s+/, "");
-    return line.trim() === "" ? "-   " : `-   ${line}`;
+export const insertBulletList = (textarea: HTMLTextAreaElement): string => {
+  const { start, end } = getTextareaSelection(textarea);
+  const value = textarea.value;
+  const { lineStart } = _getLineAtPosition(value, start);
+  const { lineEnd } = _getLineAtPosition(value, end);
+  const lines = value.substring(lineStart, lineEnd).split("\n");
+
+  const nonEmpty = lines.filter((l) => l.trim() !== "");
+  const allBullet =
+    nonEmpty.length > 0 && nonEmpty.every((l) => /^\s*-\s/.test(l));
+  const allOrdered =
+    nonEmpty.length > 0 && nonEmpty.every((l) => /^\s*\d+\.\s/.test(l));
+  const toggle = allBullet || allOrdered;
+
+  const newLines = lines.map((line) => {
+    if (allBullet) {
+      return line.trim() === "" ? line : line.replace(/^(\s*)-\s+/, "$1");
+    }
+    if (allOrdered) {
+      return line.trim() === "" ? line : line.replace(/^(\s*)\d+\.\s+/, "$1-   ");
+    }
+    if (line.trim() === "") return "-   ";
+    if (/^\s*-\s/.test(line)) return line;
+    if (/^\s*\d+\.\s/.test(line))
+      return line.replace(/^(\s*)\d+\.\s+/, "$1-   ");
+    return "-   " + line;
   });
 
+  const newContent = newLines.join("\n");
+  const newValue =
+    value.substring(0, lineStart) + newContent + value.substring(lineEnd);
+  const cursorTarget = lineStart + newLines[0].length;
+  if (toggle) {
+    _updateEditor(textarea, newValue, lineStart, lineStart + newContent.length);
+  } else {
+    _updateEditor(textarea, newValue, cursorTarget, cursorTarget);
+  }
+  return newValue;
+};
+
 export const insertOrderedList = (textarea: HTMLTextAreaElement): string => {
+  const { start, end } = getTextareaSelection(textarea);
+  const value = textarea.value;
+  const { lineStart } = _getLineAtPosition(value, start);
+  const { lineEnd } = _getLineAtPosition(value, end);
+  const lines = value.substring(lineStart, lineEnd).split("\n");
+
+  const nonEmpty = lines.filter((l) => l.trim() !== "");
+  const allOrdered =
+    nonEmpty.length > 0 && nonEmpty.every((l) => /^\s*\d+\.\s/.test(l));
+  const allBullet =
+    nonEmpty.length > 0 && nonEmpty.every((l) => /^\s*-\s/.test(l));
+  const toggle = allOrdered || allBullet;
+
   let num = 1;
-  return processLineSelection(textarea, /^\d+\.\s/, (line, _, allMatch) => {
-    if (allMatch) return line.trim() === "" ? line : line.replace(/^\d+\.\s+/, "");
+  const newLines = lines.map((line) => {
+    if (allOrdered) {
+      return line.trim() === "" ? line : line.replace(/^(\s*)\d+\.\s+/, "$1");
+    }
+    if (allBullet) {
+      if (line.trim() === "") return line;
+      return line.replace(/^(\s*)-\s+/, `$1${num++}.  `);
+    }
     if (line.trim() === "") return `${num++}.  `;
-    const clean = line.replace(/^\d+\.\s+/, "");
-    return `${num++}.  ${clean}`;
+    if (/^\s*\d+\.\s/.test(line)) {
+      const indent = line.match(/^(\s*)/)?.[1] ?? "";
+      const clean = line.replace(/^\s*\d+\.\s+/, "");
+      return `${indent}${num++}.  ${clean}`;
+    }
+    if (/^\s*-\s/.test(line)) {
+      const indent = line.match(/^(\s*)/)?.[1] ?? "";
+      const clean = line.replace(/^\s*-\s+/, "");
+      return `${indent}${num++}.  ${clean}`;
+    }
+    return `${num++}.  ${line}`;
   });
+
+  const newContent = newLines.join("\n");
+  const newValue =
+    value.substring(0, lineStart) + newContent + value.substring(lineEnd);
+  const cursorTarget = lineStart + newLines[0].length;
+  if (toggle) {
+    _updateEditor(textarea, newValue, lineStart, lineStart + newContent.length);
+  } else {
+    _updateEditor(textarea, newValue, cursorTarget, cursorTarget);
+  }
+  return newValue;
 };
 
 export const insertTaskList = (textarea: HTMLTextAreaElement): string =>

From 9e28f515bf7930776e52d1e91a0acbef58051bdf Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 10:58:06 +0200
Subject: [PATCH 23/26] =?UTF-8?q?fix(editor):=20remove=20blank=20lines=20b?=
 =?UTF-8?q?efore=20nested=20lists=20in=20RT=E2=86=92MD=20conversion?=
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

The paragraphInLi Turndown rule only stripped paragraph block-wrapping
when P was the sole child of LI. Lifting that restriction ensures P
elements inside LI are inlined even when a nested list is a sibling,
preventing a blank line from appearing before the nested list.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 app/_utils/markdown-utils.tsx | 5 +----
 1 file changed, 1 insertion(+), 4 deletions(-)

diff --git a/app/_utils/markdown-utils.tsx b/app/_utils/markdown-utils.tsx
index badc9bc2..12eb2c48 100644
--- a/app/_utils/markdown-utils.tsx
+++ b/app/_utils/markdown-utils.tsx
@@ -94,10 +94,7 @@ export const createTurndownService = (tableSyntax?: TableSyntax) => {
       const isElement = (n: ParentNode): n is HTMLElement => n.nodeType === 1;
 
       if (parent.nodeName === "LI") {
-        const elementChildren = Array.from(parent.children).filter(
-          (child) => child.nodeType === 1
-        );
-        return elementChildren.length === 1;
+        return true;
       }
       if (
         parent.nodeName === "DIV" &&

From 20a5bd2ddaf8781e1bc1adf271a8223fe449ad53 Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 11:07:05 +0200
Subject: [PATCH 24/26] fix(editor): preserve nesting depth when switching list
 type in RT mode
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Add getListDepth() to count listItem ancestors and switchListType() that
lifts the item all the way out, toggles to the new list type, then sinks
back to the original depth. This fixes the bug where switching bullet↔
ordered on a nested item always moved it to level 1.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx | 28 ++++++++++++++++---
 1 file changed, 24 insertions(+), 4 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
index 3e899053..debf9a2f 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -71,6 +71,15 @@ export const ListMenuDropdown = ({
     }
   };
 
+  const getListDepth = (): number => {
+    const { $anchor } = editor.state.selection;
+    let depth = 0;
+    for (let d = $anchor.depth; d > 0; d--) {
+      if ($anchor.node(d).type.name === "listItem") depth++;
+    }
+    return depth;
+  };
+
   const liftOutOfList = () => {
     let safety = 20;
     while (
@@ -81,6 +90,19 @@ export const ListMenuDropdown = ({
     }
   };
 
+  const switchListType = (toOrdered: boolean) => {
+    const depth = getListDepth();
+    let chain = editor.chain().focus();
+    for (let i = 0; i < depth; i++) {
+      chain = chain.liftListItem("listItem");
+    }
+    chain = toOrdered ? chain.toggleOrderedList() : chain.toggleBulletList();
+    for (let i = 1; i < depth; i++) {
+      chain = chain.sinkListItem("listItem");
+    }
+    chain.run();
+  };
+
   const handleBulletList = () => {
     if (isMarkdownMode) {
       applyMarkdown(MarkdownUtils.insertBulletList);
@@ -89,8 +111,7 @@ export const ListMenuDropdown = ({
     if (listState.isInBulletList) {
       liftOutOfList();
     } else if (listState.isInOrderedList) {
-      liftOutOfList();
-      editor.chain().focus().toggleBulletList().run();
+      switchListType(false);
     } else {
       editor.chain().focus().toggleBulletList().run();
     }
@@ -104,8 +125,7 @@ export const ListMenuDropdown = ({
     if (listState.isInOrderedList) {
       liftOutOfList();
     } else if (listState.isInBulletList) {
-      liftOutOfList();
-      editor.chain().focus().toggleOrderedList().run();
+      switchListType(true);
     } else {
       editor.chain().focus().toggleOrderedList().run();
     }

From 29eb71f8ed73c1e35f6019b853103d333fcf51dc Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 11:15:25 +0200
Subject: [PATCH 25/26] Revert "fix(editor): preserve nesting depth when
 switching list type in RT mode"

This reverts commit 20a5bd2ddaf8781e1bc1adf271a8223fe449ad53.
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx | 28 +++----------------
 1 file changed, 4 insertions(+), 24 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
index debf9a2f..3e899053 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -71,15 +71,6 @@ export const ListMenuDropdown = ({
     }
   };
 
-  const getListDepth = (): number => {
-    const { $anchor } = editor.state.selection;
-    let depth = 0;
-    for (let d = $anchor.depth; d > 0; d--) {
-      if ($anchor.node(d).type.name === "listItem") depth++;
-    }
-    return depth;
-  };
-
   const liftOutOfList = () => {
     let safety = 20;
     while (
@@ -90,19 +81,6 @@ export const ListMenuDropdown = ({
     }
   };
 
-  const switchListType = (toOrdered: boolean) => {
-    const depth = getListDepth();
-    let chain = editor.chain().focus();
-    for (let i = 0; i < depth; i++) {
-      chain = chain.liftListItem("listItem");
-    }
-    chain = toOrdered ? chain.toggleOrderedList() : chain.toggleBulletList();
-    for (let i = 1; i < depth; i++) {
-      chain = chain.sinkListItem("listItem");
-    }
-    chain.run();
-  };
-
   const handleBulletList = () => {
     if (isMarkdownMode) {
       applyMarkdown(MarkdownUtils.insertBulletList);
@@ -111,7 +89,8 @@ export const ListMenuDropdown = ({
     if (listState.isInBulletList) {
       liftOutOfList();
     } else if (listState.isInOrderedList) {
-      switchListType(false);
+      liftOutOfList();
+      editor.chain().focus().toggleBulletList().run();
     } else {
       editor.chain().focus().toggleBulletList().run();
     }
@@ -125,7 +104,8 @@ export const ListMenuDropdown = ({
     if (listState.isInOrderedList) {
       liftOutOfList();
     } else if (listState.isInBulletList) {
-      switchListType(true);
+      liftOutOfList();
+      editor.chain().focus().toggleOrderedList().run();
     } else {
       editor.chain().focus().toggleOrderedList().run();
     }

From cace53c62916792d9a1b2c6fc8e110d06f83ebcb Mon Sep 17 00:00:00 2001
From: Nikolai Andree <niko@andree-web.com>
Date: Fri, 15 May 2026 11:19:22 +0200
Subject: [PATCH 26/26] fix(editor): switch nested list type in place via
 setNodeMarkup
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Detect the innermost list type with a ProseMirror ancestor walk instead
of listState flags, which are both true for nested lists. When the
clicked type differs from the innermost list, call toggleBulletList/
toggleOrderedList directly — their internal toggleList implementation
runs setNodeMarkup on the immediate parent list and preserves nesting
depth. Same-type clicks still call liftOutOfList for a full exit.

This restores the ability to switch a level-2 bullet to a level-2
ordered list (and vice versa) without flattening to level 1.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .../Parts/TipTap/Toolbar/ListMenuDropdown.tsx | 19 +++++++++++--------
 1 file changed, 11 insertions(+), 8 deletions(-)

diff --git a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
index 3e899053..49a3b5de 100644
--- a/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
+++ b/app/_components/FeatureComponents/Notes/Parts/TipTap/Toolbar/ListMenuDropdown.tsx
@@ -71,6 +71,15 @@ export const ListMenuDropdown = ({
     }
   };
 
+  const getCurrentListType = (): "bulletList" | "orderedList" | null => {
+    const { $from } = editor.state.selection;
+    for (let d = $from.depth; d > 0; d--) {
+      const name = $from.node(d).type.name;
+      if (name === "bulletList" || name === "orderedList") return name;
+    }
+    return null;
+  };
+
   const liftOutOfList = () => {
     let safety = 20;
     while (
@@ -86,11 +95,8 @@ export const ListMenuDropdown = ({
       applyMarkdown(MarkdownUtils.insertBulletList);
       return;
     }
-    if (listState.isInBulletList) {
-      liftOutOfList();
-    } else if (listState.isInOrderedList) {
+    if (getCurrentListType() === "bulletList") {
       liftOutOfList();
-      editor.chain().focus().toggleBulletList().run();
     } else {
       editor.chain().focus().toggleBulletList().run();
     }
@@ -101,11 +107,8 @@ export const ListMenuDropdown = ({
       applyMarkdown(MarkdownUtils.insertOrderedList);
       return;
     }
-    if (listState.isInOrderedList) {
-      liftOutOfList();
-    } else if (listState.isInBulletList) {
+    if (getCurrentListType() === "orderedList") {
       liftOutOfList();
-      editor.chain().focus().toggleOrderedList().run();
     } else {
       editor.chain().focus().toggleOrderedList().run();
     }