diff --git a/plugins/unsloth-chat/index.jsx b/plugins/unsloth-chat/index.jsx
index 1437a82..4ca7812 100644
--- a/plugins/unsloth-chat/index.jsx
+++ b/plugins/unsloth-chat/index.jsx
@@ -655,52 +655,104 @@ function createMenuItem(label, iconSvg, onClick) {
   return el;
 }
 
-// ── Inject items into the + menu popout ─────────────────────────
-function injectPlusMenuItems() {
-  // Look for open menu scrollers — the + popout is a menu layer
-  const scrollers = document.querySelectorAll('[class*="menu"] [class*="scroller"]');
-  for (const scroller of scrollers) {
-    // Already injected?
-    if (scroller.querySelector("[data-unsloth-menu-item]")) continue;
-
-    // Identify the + menu: it contains items for upload / create thread etc.
-    // We look for any element that hints this is the channel-attach popout.
-    const hint =
-      scroller.querySelector('[class*="upload"], [class*="attach"]') ||
-      scroller.closest('[class*="channelTextArea"]');
-    if (!hint) continue;
-
-    // Append a divider then our two items
-    const divider = document.createElement("div");
-    divider.style.cssText =
-      "margin:4px 6px;border-top:1px solid var(--background-modifier-accent);";
-
-    const askAi = createMenuItem("Ask AI", SPARKLE_ICON, () => {
-      openModal((p) => <PromptModal close={p.close} />);
-    });
-
-    const suggest = createMenuItem("Suggest reply", REPLY_ICON, () => {
-      suggestReply();
-    });
-
-    scroller.appendChild(divider);
-    scroller.appendChild(askAi);
-    scroller.appendChild(suggest);
+// ── Identify the + popout and inject items ──────────────────────
+function isAttachMenu(scroller) {
+  // Check menu item text for keywords unique to the + popout
+  const items = scroller.querySelectorAll('[role="menuitem"], [class*="item"]');
+  for (const item of items) {
+    const t = (item.textContent || "").toLowerCase();
+    if (/upload|file|thread|create|attach|app|integration|gif|sticker|poll/i.test(t)) {
+      return true;
+    }
   }
+
+  // Fallback: is the popout positioned near the chat input area?
+  const menuRoot = scroller.closest('[class*="menu"]') || scroller.closest('[class*="popout"]');
+  if (menuRoot) {
+    const cta = document.querySelector('[class*="channelTextArea"]');
+    if (cta) {
+      const mr = menuRoot.getBoundingClientRect();
+      const cr = cta.getBoundingClientRect();
+      if (mr.bottom >= cr.top - 20 && mr.top <= cr.bottom + 20) return true;
+    }
+  }
+
+  return false;
 }
 
-// ── Hook the + button to inject items when popout opens ──────────
+function addItemsToScroller(scroller) {
+  if (!scroller || scroller.querySelector("[data-unsloth-menu-item]")) return;
+
+  const divider = document.createElement("div");
+  divider.style.cssText =
+    "margin:4px 6px;border-top:1px solid var(--background-modifier-accent);";
+
+  const askAi = createMenuItem("Ask AI", SPARKLE_ICON, () => {
+    openModal((p) => <PromptModal close={p.close} />);
+  });
+
+  const suggest = createMenuItem("Suggest reply", REPLY_ICON, () => {
+    suggestReply();
+  });
+
+  scroller.appendChild(divider);
+  scroller.appendChild(askAi);
+  scroller.appendChild(suggest);
+}
+
+// ── Strategy 1: MutationObserver watches for any menu popout ────
+const menuObserver = new MutationObserver((mutations) => {
+  for (const mut of mutations) {
+    for (const node of mut.addedNodes) {
+      if (node.nodeType !== Node.ELEMENT_NODE) continue;
+      // The added node may be the menu itself …
+      if (node.matches && node.matches('[class*="menu"]')) {
+        const sc = node.querySelector('[class*="scroller"]');
+        if (sc && isAttachMenu(sc)) addItemsToScroller(sc);
+      }
+      // … or it may contain a menu subtree deeper inside (portals)
+      if (node.querySelectorAll) {
+        node.querySelectorAll('[class*="menu"]').forEach(menu => {
+          const sc = menu.querySelector('[class*="scroller"]');
+          if (sc && isAttachMenu(sc)) addItemsToScroller(sc);
+        });
+      }
+    }
+  }
+});
+menuObserver.observe(document.body, { childList: true, subtree: true });
+scoped.onDispose(() => menuObserver.disconnect());
+
+// ── Strategy 2: hook the + button click for faster injection ────
 function hookAttachButton(btn) {
   if (btn.dataset.unslothHooked) return;
   btn.dataset.unslothHooked = "1";
   btn.addEventListener("click", () => {
-    // The popout renders asynchronously, so wait a tick
-    setTimeout(injectPlusMenuItems, 50);
+    let tries = 0;
+    const poll = () => {
+      if (tries++ > 15) return;
+      const scrollers = document.querySelectorAll('[class*="menu"] [class*="scroller"]');
+      for (const sc of scrollers) {
+        if (!sc.querySelector("[data-unsloth-menu-item]") && isAttachMenu(sc)) {
+          addItemsToScroller(sc);
+          return;
+        }
+      }
+      setTimeout(poll, 40);
+    };
+    setTimeout(poll, 30);
   });
 }
 
+// Multiple possible selectors for the + button (Discord changes these)
 scoped.observeDom(
-  '[class*="channelTextArea"] [class*="attachButton"]',
+  [
+    '[class*="channelTextArea"] [class*="attachButton"]',
+    '[class*="channelTextArea"] [class*="attachWrapper"] > button',
+    '[class*="channelTextArea"] button[class*="attach"]',
+    '[class*="channelTextArea"] [aria-label*="ttach"]',
+    '[class*="channelTextArea"] [class*="uploadInput"]',
+  ].join(", "),
   hookAttachButton,
 );