diff --git a/src/gui/src/UI/UIItem.js b/src/gui/src/UI/UIItem.js
index f502aafea6..16f9cfa46d 100644
--- a/src/gui/src/UI/UIItem.js
+++ b/src/gui/src/UI/UIItem.js
@@ -32,6 +32,81 @@ import launch_app from "../helpers/launch_app.js"
 import open_item from "../helpers/open_item.js"
 import mime from "../lib/mime.js";
 
+const AI_APP_NAME = 'ai';
+
+const parseItemMetadataForAI = (metadata) => {
+    if (!metadata) {
+        return undefined;
+    }
+    try {
+        return JSON.parse(metadata);
+    } catch (error) {
+        console.warn('Failed to parse item metadata for AI payload.', error);
+        return undefined;
+    }
+};
+
+const buildAIPayloadFromItems = ($elements) => {
+    return $elements.get().map((element) => {
+        const $element = $(element);
+        return {
+            uid: $element.attr('data-uid'),
+            path: $element.attr('data-path'),
+            name: $element.attr('data-name'),
+            is_dir: $element.attr('data-is_dir') === '1',
+            is_shortcut: $element.attr('data-is_shortcut') === '1',
+            shortcut_to: $element.attr('data-shortcut_to') || undefined,
+            shortcut_to_path: $element.attr('data-shortcut_to_path') || undefined,
+            size: $element.attr('data-size') || undefined,
+            type: $element.attr('data-type') || undefined,
+            modified: $element.attr('data-modified') || undefined,
+            metadata: parseItemMetadataForAI($element.attr('data-metadata')),
+        };
+    });
+};
+
+const ensureAIAppIframe = async () => {
+    let $aiWindow = $(`.window[data-app="${AI_APP_NAME}"]`);
+    if ($aiWindow.length === 0) {
+        try {
+            await launch_app({ name: AI_APP_NAME });
+        } catch (error) {
+            console.error('Failed to launch AI app.', error);
+            return null;
+        }
+        $aiWindow = $(`.window[data-app="${AI_APP_NAME}"]`);
+    }
+
+    if ($aiWindow.length === 0) {
+        return null;
+    }
+
+    $aiWindow.makeWindowVisible();
+    const iframe = $aiWindow.find('.window-app-iframe').get(0);
+    return iframe ?? null;
+};
+
+const sendSelectionToAIApp = async ($elements) => {
+    const items = buildAIPayloadFromItems($elements);
+    if (items.length === 0) {
+        return;
+    }
+
+    const aiIframe = await ensureAIAppIframe();
+    if (!aiIframe || !aiIframe.contentWindow) {
+        await UIAlert({
+            message: i18n('ai_app_unavailable'),
+        });
+        return;
+    }
+
+    aiIframe.contentWindow.postMessage({
+        msg: 'ai:openFsEntries',
+        items,
+        source: 'desktop-context-menu',
+    }, '*');
+};
+
 function UIItem(options){
     const matching_appendto_count = $(options.appendTo).length;
     if(matching_appendto_count > 1){
@@ -850,6 +925,15 @@ function UIItem(options){
                     }
                 })
                 // -------------------------------------------
+                // Open in AI
+                // -------------------------------------------
+                menu_items.push({
+                    html: i18n('open_in_ai'),
+                    onClick: async function(){
+                        await sendSelectionToAIApp($selected_items);
+                    }
+                });
+                // -------------------------------------------
                 // -
                 // -------------------------------------------
                 menu_items.push({ is_divider: true });
@@ -1178,6 +1262,15 @@ function UIItem(options){
                         UIWindowShare([{uid: $(el_item).attr('data-uid'), path: $(el_item).attr('data-path'), name: $(el_item).attr('data-name'), icon: $(el_item_icon).find('img').attr('src')}]);
                     }
                 });
+                // -------------------------------------------
+                // Open in AI
+                // -------------------------------------------
+                menu_items.push({
+                    html: i18n('open_in_ai'),
+                    onClick: async function(){
+                        await sendSelectionToAIApp($(el_item));
+                    }
+                });
             }
 
             // -------------------------------------------
@@ -1753,4 +1846,4 @@ window.activate_item_name_editor= function(el_item){
         $(el_item_name_editor).select();
 }
 
-export default UIItem;
\ No newline at end of file
+export default UIItem;
diff --git a/src/gui/src/i18n/translations/en.js b/src/gui/src/i18n/translations/en.js
index 2b1ac4073f..10c6409c6c 100644
--- a/src/gui/src/i18n/translations/en.js
+++ b/src/gui/src/i18n/translations/en.js
@@ -137,6 +137,7 @@ const en = {
         enter_password_to_confirm_delete_user: "Enter your password to confirm account deletion",
         error_message_is_missing: "Error message is missing.",
         error_unknown_cause: "An unknown error occurred.",
+        ai_app_unavailable: "The AI app isn't available right now. Please try again in a moment.",
         error_uploading_files: "Failed to upload files",
         favorites: "Favorites",
         feedback: "Feedback",
@@ -197,6 +198,7 @@ const en = {
         new_window: "New Window",
         open_in_new_tab: "Open in New Tab",
         open_in_new_window: "Open in New Window",
+        open_in_ai: "Open in AI",
         open_trash: "Open Trash",
         open_with: "Open With",
         original_name: 'Original Name',
@@ -520,4 +522,4 @@ const en = {
     }
 };
 
-export default en;
\ No newline at end of file
+export default en;