diff --git a/client/src/components/tools/CreateTodoToolUI.tsx b/client/src/components/tools/CreateTodoToolUI.tsx
index 32d67a6..ac34dce 100644
--- a/client/src/components/tools/CreateTodoToolUI.tsx
+++ b/client/src/components/tools/CreateTodoToolUI.tsx
@@ -1,14 +1,17 @@
 import { makeAssistantToolUI } from "@assistant-ui/react";
 import { useEffect, useRef } from "react";
 import { queryClient } from "@/lib/queryClient";
+import { FileText } from "lucide-react";
 
 type CreateTodoArgs = {
   item: string;
+  files?: string[];
 };
 
 type CreateTodoResult = {
   id: number;
   item: string;
+  files?: string[];
   createdAt: string | Date;
 };
 
@@ -19,6 +22,12 @@ export const CreateTodoToolUI = makeAssistantToolUI<CreateTodoArgs, CreateTodoRe
       return (
         <div className="rounded border p-3 text-sm">
           Creating todo: <span className="font-medium">{args.item}</span>
+          {args.files && args.files.length > 0 && (
+            <div className="mt-2 text-xs text-muted-foreground">
+              <FileText className="inline h-3 w-3 mr-1" />
+              {args.files.length} file{args.files.length > 1 ? 's' : ''} attached
+            </div>
+          )}
         </div>
       );
     }
@@ -61,6 +70,22 @@ export const CreateTodoToolUI = makeAssistantToolUI<CreateTodoArgs, CreateTodoRe
         <InvalidateOnSuccess enabled={true} />
         <div className="font-medium">Todo created</div>
         <div className="mt-1">{result.item}</div>
+        {result.files && result.files.length > 0 && (
+          <div className="mt-2 space-y-1">
+            <div className="text-xs font-medium text-muted-foreground flex items-center">
+              <FileText className="h-3 w-3 mr-1" />
+              Attached files:
+            </div>
+            <div className="space-y-1">
+              {result.files.map((file, index) => (
+                <div key={index} className="text-xs bg-muted/50 px-2 py-1 rounded flex items-center">
+                  <FileText className="h-3 w-3 mr-1 text-muted-foreground" />
+                  <span className="truncate">{file.split('/').pop() || file}</span>
+                </div>
+              ))}
+            </div>
+          </div>
+        )}
       </div>
     );
   },
diff --git a/client/src/pages/dashboard.tsx b/client/src/pages/dashboard.tsx
index 1d66b32..3b7ddee 100644
--- a/client/src/pages/dashboard.tsx
+++ b/client/src/pages/dashboard.tsx
@@ -5,7 +5,7 @@ import { useAuth } from "@/hooks/useAuth";
 import { Button } from "@/components/ui/button";
 import { useToast } from "@/hooks/useToast";
 import { SearchBar } from "@/components/SearchBar";
-import { Plus } from "lucide-react";
+import { Plus, FileText } from "lucide-react";
 import { apiRequest } from "@/lib/queryClient";
 import { Dialog, DialogContent, DialogHeader, DialogTitle } from "@/components/ui/dialog";
 import { Input } from "@/components/ui/input";
@@ -184,6 +184,7 @@ export default function Dashboard() {
           <TableHeader>
             <TableRow>
               <TableHead>Item</TableHead>
+              <TableHead>Files</TableHead>
               <TableHead className="w-[100px]">Actions</TableHead>
             </TableRow>
           </TableHeader>
@@ -191,6 +192,20 @@ export default function Dashboard() {
             {filteredItems.map((item) => (
               <TableRow key={item.id}>
                 <TableCell>{item.item}</TableCell>
+                <TableCell>
+                  {item.files && item.files.length > 0 ? (
+                    <div className="flex flex-wrap gap-1">
+                      {item.files.map((file, index) => (
+                        <div key={index} className="flex items-center gap-1 text-xs bg-muted/50 px-2 py-1 rounded">
+                          <FileText className="h-3 w-3 text-muted-foreground" />
+                          <span className="truncate max-w-[100px]">{file.split('/').pop() || file}</span>
+                        </div>
+                      ))}
+                    </div>
+                  ) : (
+                    <span className="text-muted-foreground text-sm">No files</span>
+                  )}
+                </TableCell>
                 <TableCell>
                   <Button
                     variant="destructive"
diff --git a/migrations/0002_add_files_to_items.sql b/migrations/0002_add_files_to_items.sql
new file mode 100644
index 0000000..809c94b
--- /dev/null
+++ b/migrations/0002_add_files_to_items.sql
@@ -0,0 +1,2 @@
+-- Add files column to items table to store associated file paths
+ALTER TABLE "items" ADD COLUMN "files" text[];
\ No newline at end of file
diff --git a/package-lock.json b/package-lock.json
index e35fe44..8ec0545 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -58,7 +58,7 @@
         "cmdk": "^1.0.0",
         "cors": "^2.8.5",
         "date-fns": "^3.6.0",
-        "dotenv": "^16.5.0",
+        "dotenv": "^16.6.1",
         "drizzle-orm": "^0.39.1",
         "drizzle-zod": "^0.7.0",
         "embla-carousel-react": "^8.3.0",
@@ -126,6 +126,9 @@
         "typescript": "5.6.3",
         "vite": "^7.0.6"
       },
+      "engines": {
+        "node": ">=22 <23"
+      },
       "optionalDependencies": {
         "bufferutil": "^4.0.8"
       }
@@ -9432,9 +9435,10 @@
       }
     },
     "node_modules/dotenv": {
-      "version": "16.5.0",
-      "resolved": "https://registry.npmjs.org/dotenv/-/dotenv-16.5.0.tgz",
-      "integrity": "sha512-m/C+AwOAr9/W1UOIZUo232ejMNnJAJtYQjUbHoNTBNTJSvqzzDh7vnrei3o3r3m9blf6ZoDkvcw0VmozNRFJxg==",
+      "version": "16.6.1",
+      "resolved": "https://registry.npmjs.org/dotenv/-/dotenv-16.6.1.tgz",
+      "integrity": "sha512-uBq4egWHTcTt33a72vpSG0z3HnPuIl6NqYcTrKEg2azoEyl2hpW0zqlxysq2pK9HlDIHyHyakeYaYnSAwd8bow==",
+      "license": "BSD-2-Clause",
       "engines": {
         "node": ">=12"
       },
diff --git a/package.json b/package.json
index d5a5b3e..f17cd09 100644
--- a/package.json
+++ b/package.json
@@ -70,16 +70,14 @@
     "class-variance-authority": "^0.7.1",
     "clsx": "^2.1.1",
     "cmdk": "^1.0.0",
-    
     "cors": "^2.8.5",
     "date-fns": "^3.6.0",
-    "dotenv": "^16.5.0",
+    "dotenv": "^16.6.1",
     "drizzle-orm": "^0.39.1",
     "drizzle-zod": "^0.7.0",
     "embla-carousel-react": "^8.3.0",
     "express": "^4.21.2",
     "express-rate-limit": "^8.0.1",
-    
     "firebase": "^11.3.1",
     "firebase-admin": "^13.4.0",
     "framer-motion": "^11.13.1",
@@ -88,8 +86,6 @@
     "input-otp": "^1.2.4",
     "jest-environment-jsdom": "^29.7.0",
     "lucide-react": "^0.453.0",
-    
-    
     "multer": "^2.0.1",
     "passport": "^0.7.0",
     "passport-local": "^1.0.0",
@@ -122,9 +118,7 @@
     "@tailwindcss/typography": "^0.5.15",
     "@testing-library/jest-dom": "^6.6.4",
     "@testing-library/react": "^16.3.0",
-    
     "@types/express": "4.17.21",
-    
     "@types/jest": "^30.0.0",
     "@types/node": "^20.16.11",
     "@types/passport": "^1.0.16",
diff --git a/server/routes/aiRoutes.ts b/server/routes/aiRoutes.ts
index a019922..6d9d80d 100644
--- a/server/routes/aiRoutes.ts
+++ b/server/routes/aiRoutes.ts
@@ -135,9 +135,10 @@ export async function registerAIRoutes(app: Express) {
             description: "Create a new todo item for the current user",
             parameters: z.object({
               item: z.string().min(1).max(1000).describe("The todo item text"),
+              files: z.array(z.string()).optional().describe("Optional array of file paths to associate with this todo"),
             }),
-            execute: async ({ item }) => {
-              console.log('[createTodo] start', { item, userId });
+            execute: async ({ item, files }) => {
+              console.log('[createTodo] start', { item, files, userId });
               const currentUserId = userId;
               // Enforce simple free-tier limit (mirror itemRoutes)
               const user = await storage.getUserByFirebaseId(currentUserId);
@@ -147,9 +148,9 @@ export async function registerAIRoutes(app: Express) {
                 return { ok: false, error: 'Free plan item limit reached. Upgrade to Pro to add more todos.' };
               }
               try {
-                const created = await storage.createItem({ userId: currentUserId, item });
+                const created = await storage.createItem({ userId: currentUserId, item, files });
                 console.log('[createTodo] success', { id: created.id });
-                return { ok: true, id: created.id, item: created.item, createdAt: new Date().toISOString() };
+                return { ok: true, id: created.id, item: created.item, files: created.files, createdAt: new Date().toISOString() };
               } catch (err) {
                 console.error('[createTodo] error', err);
                 return { ok: false, error: 'Failed to create todo. Please try again.' };
diff --git a/server/storage/ItemStorage.ts b/server/storage/ItemStorage.ts
index 8acb456..d826f08 100644
--- a/server/storage/ItemStorage.ts
+++ b/server/storage/ItemStorage.ts
@@ -15,4 +15,35 @@ export class ItemStorage {
   async deleteItem(id: number): Promise<void> {
     await db.delete(items).where(eq(items.id, id));
   }
+
+  async updateItemFiles(id: number, filePaths: string[]): Promise<Item | null> {
+    const [updatedItem] = await db
+      .update(items)
+      .set({ files: filePaths })
+      .where(eq(items.id, id))
+      .returning();
+    return updatedItem || null;
+  }
+
+  async addFileToItem(id: number, filePath: string): Promise<Item | null> {
+    // First get the current item to append to existing files
+    const [currentItem] = await db.select().from(items).where(eq(items.id, id));
+    if (!currentItem) return null;
+    
+    const currentFiles = currentItem.files || [];
+    const updatedFiles = [...currentFiles, filePath];
+    
+    return this.updateItemFiles(id, updatedFiles);
+  }
+
+  async removeFileFromItem(id: number, filePath: string): Promise<Item | null> {
+    // First get the current item to remove from existing files
+    const [currentItem] = await db.select().from(items).where(eq(items.id, id));
+    if (!currentItem) return null;
+    
+    const currentFiles = currentItem.files || [];
+    const updatedFiles = currentFiles.filter(file => file !== filePath);
+    
+    return this.updateItemFiles(id, updatedFiles);
+  }
 }
\ No newline at end of file
diff --git a/shared/schema.ts b/shared/schema.ts
index 7c8ede0..6346aea 100644
--- a/shared/schema.ts
+++ b/shared/schema.ts
@@ -30,6 +30,7 @@ export const items = pgTable("items", {
   id: serial("id").primaryKey(),
   item: text("item").notNull(),
   userId: text("user_id").notNull().references(() => users.firebaseId),
+  files: text("files").array(), // Array of file paths or identifiers
 });
 
 export const files = pgTable("files", {
@@ -114,6 +115,7 @@ export const insertUserSchema = createInsertSchema(users, {
 export const insertItemSchema = createInsertSchema(items, {
   userId: z.string(),
   item: z.string(),
+  files: z.array(z.string()).optional(), // Optional array of file paths
 });
 
 export const insertFileSchema = createInsertSchema(files, {