diff --git a/schema/chat.json b/schema/chat.json
index 0e79f64..e96a484 100644
--- a/schema/chat.json
+++ b/schema/chat.json
@@ -22,6 +22,12 @@
       "title": "AI persona name",
       "description": "The name of the AI persona",
       "default": "Jupyternaut"
+    },
+    "enableFileAttachment": {
+      "type": "boolean",
+      "title": "Enable file attachment support",
+      "default": false,
+      "description": "This allow you to sending attached files along with your message. ⚠️ This may send large content to the LLM, consuming many tokens."
     }
   },
   "additionalProperties": false
diff --git a/src/chat-handler.ts b/src/chat-handler.ts
index 4d10fe5..ba2a9d3 100644
--- a/src/chat-handler.ts
+++ b/src/chat-handler.ts
@@ -39,12 +39,12 @@ export const welcomeMessage = (providers: string[]) => `
 #### Ask JupyterLite AI
 
 
-The provider to use can be set in the <button data-commandLinker-command="settingeditor:open" data-commandLinker-args='{"query": "AI provider"}' href="#">settings editor</button>, by selecting it from
-the <img src="${AI_AVATAR}" width="16" height="16"> _AI provider_ settings.
+The provider to use can be set in the <button data-commandLinker-command="settingeditor:open" data-commandLinker-args='{"query": "AI providers"}' href="#">settings editor</button>, by selecting it from
+the <img src="${AI_AVATAR}" width="16" height="16"> _AI providers_ settings.
 
 The current providers that are available are _${providers.sort().join('_, _')}_.
 
-To clear the chat, you can use the \`/clear\` command from the chat input.
+- To clear the chat, you can use the \`/clear\` command from the chat input.
 `;
 
 export type ConnectionMessage = {
diff --git a/src/index.ts b/src/index.ts
index 06e870d..8fe94b1 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -20,6 +20,7 @@ import { ISettingRegistry } from '@jupyterlab/settingregistry';
 import { IFormRendererRegistry } from '@jupyterlab/ui-components';
 import { ReadonlyPartialJSONObject } from '@lumino/coreutils';
 import { ISecretsManager, SecretsManager } from 'jupyter-secrets-manager';
+import { IDocumentManager } from '@jupyterlab/docmanager';
 
 import { ChatHandler, welcomeMessage } from './chat-handler';
 import { CompletionProvider } from './completion-provider';
@@ -50,7 +51,8 @@ const chatPlugin: JupyterFrontEndPlugin<void> = {
     INotebookTracker,
     ISettingRegistry,
     IThemeManager,
-    ILayoutRestorer
+    ILayoutRestorer,
+    IDocumentManager
   ],
   activate: async (
     app: JupyterFrontEnd,
@@ -60,7 +62,8 @@ const chatPlugin: JupyterFrontEndPlugin<void> = {
     notebookTracker: INotebookTracker | null,
     settingsRegistry: ISettingRegistry | null,
     themeManager: IThemeManager | null,
-    restorer: ILayoutRestorer | null
+    restorer: ILayoutRestorer | null,
+    docManager: IDocumentManager | null
   ) => {
     let activeCellManager: IActiveCellManager | null = null;
     if (notebookTracker) {
@@ -72,22 +75,33 @@ const chatPlugin: JupyterFrontEndPlugin<void> = {
 
     const chatHandler = new ChatHandler({
       providerRegistry,
-      activeCellManager
+      activeCellManager,
+      documentManager: docManager ?? undefined
     });
 
     let sendWithShiftEnter = false;
     let enableCodeToolbar = true;
+    let enableFileAttachment = false;
     let personaName = 'AI';
 
     function loadSetting(setting: ISettingRegistry.ISettings): void {
       sendWithShiftEnter = setting.get('sendWithShiftEnter')
-        .composite as boolean;
-      enableCodeToolbar = setting.get('enableCodeToolbar').composite as boolean;
-      personaName = setting.get('personaName').composite as string;
+        ?.composite as boolean;
+      enableCodeToolbar = setting.get('enableCodeToolbar')
+        ?.composite as boolean;
+      personaName = setting.get('personaName')?.composite as string;
+      enableFileAttachment = setting.get('enableFileAttachment')
+        ?.composite as boolean;
 
       // set the properties
       chatHandler.config = { sendWithShiftEnter, enableCodeToolbar };
       chatHandler.personaName = personaName;
+
+      if (enableFileAttachment) {
+        inputToolbarRegistry.show('attach');
+      } else {
+        inputToolbarRegistry.hide('attach');
+      }
     }
 
     Promise.all([app.restored, settingsRegistry?.load(chatPlugin.id)])