frontend/src/features/workspace/DocumentEditor.tsx

@@ -1029,6 +1029,25 @@ export const DocumentEditor: React.FC<DocumentEditorProps> = ({
     [effectiveCanEdit, isLiveEnabled, sendBlockUpdated]
   );
 
+  const handleUpdateBlocks = useCallback(
+    (updatedBlocks: DocumentBlock[]) => {
+      if (!effectiveCanEdit || updatedBlocks.length === 0) return;
+      const map = new Map<string, DocumentBlock>();
+      for (const b of updatedBlocks) {
+        map.set(b.id, b);
+      }
+      setBlocks((prev) =>
+        prev.map((b) => map.get(b.id) || b)
+      );
+      if (isLiveEnabled) {
+        for (const b of updatedBlocks) {
+          sendBlockUpdated(b);
+        }
+      }
+    },
+    [effectiveCanEdit, isLiveEnabled, sendBlockUpdated]
+  );
+
   const handleCreateBlock = useCallback(
     (newBlock: DocumentBlock, afterBlockId?: string) => {
       if (!effectiveCanEdit) return;
@@ -1531,6 +1550,7 @@ export const DocumentEditor: React.FC<DocumentEditorProps> = ({
                 remoteCursors={remoteCursors}
                 sendCursorMoved={sendCursorMoved}
                 onUpdateBlock={handleUpdateBlock}
+                onUpdateBlocks={handleUpdateBlocks}
                 onCreateBlock={handleCreateBlock}
                 onDeleteBlock={handleDeleteBlock}
                 onMoveBlock={handleMoveBlock}
@@ -1599,6 +1619,7 @@ export const DocumentEditor: React.FC<DocumentEditorProps> = ({
               remoteCursors={remoteCursors}
               sendCursorMoved={sendCursorMoved}
               onUpdateBlock={handleUpdateBlock}
+              onUpdateBlocks={handleUpdateBlocks}
               onCreateBlock={handleCreateBlock}
               onDeleteBlock={handleDeleteBlock}
               onMoveBlock={handleMoveBlock}

frontend/src/features/workspace/OutlinerTree.tsx

@@ -13,6 +13,7 @@ export interface OutlinerTreeProps {
   remoteCursors?: Record<string, RemoteCursor>;
   sendCursorMoved?: (blockId: string | null, selectionStart?: number, selectionEnd?: number) => void;
   onUpdateBlock: (updated: DocumentBlock, immediate?: boolean) => void;
+  onUpdateBlocks?: (updated: DocumentBlock[]) => void;
   onCreateBlock: (newBlock: DocumentBlock, afterBlockId?: string) => void;
   onDeleteBlock: (blockId: string) => void;
   onMoveBlock: (blockId: string, newIndex: number, level?: number) => void;
@@ -34,6 +35,7 @@ export const OutlinerTree: React.FC<OutlinerTreeProps> = ({
   remoteCursors,
   sendCursorMoved,
   onUpdateBlock,
+  onUpdateBlocks,
   onCreateBlock,
   onDeleteBlock,
   onMoveBlock,
@@ -172,7 +174,7 @@ export const OutlinerTree: React.FC<OutlinerTreeProps> = ({
     }
 
     return result;
-  }, [blocks]);
+  }, [blocks, levelOffset]);
 
   const handleCreateBlockBelow = useCallback(
     (afterBlockId: string, _currentContent: string) => {
@@ -241,9 +243,9 @@ export const OutlinerTree: React.FC<OutlinerTreeProps> = ({
       const current = blocks[idx];
       const currentLevel = Math.max(0, current.level || 0);
       const prevLevel = idx > 0 ? Math.max(0, blocks[idx - 1].level || 0) : 0;
-      const maxLevel = idx === 0 ? 0 : prevLevel + 1;
-
       const minLevel = levelOffset || 0;
+      const maxLevel = idx === 0 ? minLevel : prevLevel + 1;
+
       const nextLevel =
         delta === 1
           ? Math.min(maxLevel, currentLevel + 1)
@@ -251,15 +253,38 @@ export const OutlinerTree: React.FC<OutlinerTreeProps> = ({
 
       if (nextLevel === currentLevel) return;
 
-      onUpdateBlock(
-        {
-          ...current,
-          level: nextLevel,
-        },
-        true
-      );
+      const actualDelta = nextLevel - currentLevel;
+
+      // Find all contiguous children / descendants:
+      // contiguous blocks with level > currentLevel
+      let count = 1;
+      for (let i = idx + 1; i < blocks.length; i++) {
+        if (Math.max(0, blocks[i].level || 0) > currentLevel) {
+          count++;
+        } else {
+          break;
+        }
+      }
+
+      const updatedBlocks: DocumentBlock[] = [];
+      for (let i = idx; i < idx + count; i++) {
+        const b = blocks[i];
+        const newLvl = Math.max(minLevel, (b.level || 0) + actualDelta);
+        updatedBlocks.push({
+          ...b,
+          level: newLvl,
+        });
+      }
+
+      if (onUpdateBlocks) {
+        onUpdateBlocks(updatedBlocks);
+      } else {
+        for (const b of updatedBlocks) {
+          onUpdateBlock(b, true);
+        }
+      }
     },
-    [blocks, canEdit, onUpdateBlock]
+    [blocks, canEdit, levelOffset, onUpdateBlock, onUpdateBlocks]
   );
 
   const handleNavigateFocus = useCallback(