diff --git a/src/components/SearchDialog.tsx b/src/components/SearchDialog.tsx
index 203dab2..906057a 100644
--- a/src/components/SearchDialog.tsx
+++ b/src/components/SearchDialog.tsx
@@ -25,8 +25,11 @@ import {
 } from "@/lib/search.shared";
 import { createStaticSearchClient, preloadStaticSearch } from "@/lib/static-search-client";
 import { closeSuperchat, isSuperchatOpen, openSuperchat } from "@/lib/superchat";
+import { cn } from "@/lib/cn";
 import { buildDocsApiPath } from "@/lib/url-base";
 
+const SEARCH_DELAY_MS = 100;
+
 function scheduleIdle(callback: () => void) {
   if (typeof window === "undefined") return () => undefined;
 
@@ -41,6 +44,8 @@ function scheduleIdle(callback: () => void) {
 
 export function CustomSearchDialog(props: SharedProps) {
   const [scope, setScope] = useState<SearchScope | undefined>();
+  const [debouncedSearch, setDebouncedSearch] = useState("");
+  const [isAskAIHintActive, setIsAskAIHintActive] = useState(false);
   const tags = getSearchGroupsForScope(scope);
   const client =
     process.env.NODE_ENV === "production"
@@ -54,14 +59,48 @@ export function CustomSearchDialog(props: SharedProps) {
         });
   const { search, setSearch, query } = useDocsSearch({
     client,
-    delayMs: 100,
+    delayMs: SEARCH_DELAY_MS,
   });
+  const isSearchSettled = search.trim() === debouncedSearch.trim();
+  const hasConfirmedNoResults =
+    debouncedSearch.trim().length > 0 &&
+    isSearchSettled &&
+    !query.isLoading &&
+    !query.error &&
+    Array.isArray(query.data) &&
+    query.data.length === 0;
+  const hasConfirmedResults =
+    debouncedSearch.trim().length > 0 &&
+    isSearchSettled &&
+    !query.isLoading &&
+    !query.error &&
+    Array.isArray(query.data) &&
+    query.data.length > 0;
   const launchSuperchat = useEffectEvent((message = search) => {
     const seededMessage = message.trim();
     if (!openSuperchat(seededMessage)) return;
     props.onOpenChange(false);
   });
 
+  useEffect(() => {
+    const handle = window.setTimeout(() => {
+      setDebouncedSearch(search);
+    }, SEARCH_DELAY_MS);
+
+    return () => window.clearTimeout(handle);
+  }, [search]);
+
+  useEffect(() => {
+    if (hasConfirmedNoResults) {
+      setIsAskAIHintActive(true);
+      return;
+    }
+
+    if (debouncedSearch.trim().length === 0 || query.error || hasConfirmedResults) {
+      setIsAskAIHintActive(false);
+    }
+  }, [debouncedSearch, hasConfirmedNoResults, hasConfirmedResults, query.error]);
+
   useEffect(() => {
     if (process.env.NODE_ENV !== "production") return;
     const saveData = Boolean(
@@ -113,13 +152,22 @@ export function CustomSearchDialog(props: SharedProps) {
           <button
             type="button"
             onClick={() => launchSuperchat()}
-            className="group relative inline-flex items-center gap-2 rounded-full border border-[#76f4f226] bg-[#111828] px-3 py-1.5 text-sm font-medium text-[#76f4f2] shadow-[0_16px_28px_-16px_rgba(0,0,0,0.3),0_0_0_1px_rgba(118,244,242,0.08)] transition-[transform,box-shadow] duration-200 ease-[cubic-bezier(.16,1,.3,1)] hover:scale-[1.02] hover:shadow-[0_20px_30px_-14px_rgba(0,0,0,0.3),0_0_20px_-4px_rgba(118,244,242,0.25),0_0_0_1px_rgba(118,244,242,0.15)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-[#76f4f240] focus-visible:ring-offset-2 focus-visible:ring-offset-fd-background active:scale-[0.98]"
+            data-ai-hint={isAskAIHintActive ? "true" : "false"}
+            className={cn(
+              "ask-ai-button group relative inline-flex items-center gap-2 rounded-full border border-[#76f4f226] bg-[#111828] px-3 py-1.5 text-sm font-medium text-[#76f4f2] shadow-[0_16px_28px_-16px_rgba(0,0,0,0.3),0_0_0_1px_rgba(118,244,242,0.08)] transition-[transform,box-shadow,border-color] duration-200 ease-[cubic-bezier(.16,1,.3,1)] hover:scale-[1.02] hover:shadow-[0_20px_30px_-14px_rgba(0,0,0,0.3),0_0_20px_-4px_rgba(118,244,242,0.25),0_0_0_1px_rgba(118,244,242,0.15)] focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-[#76f4f240] focus-visible:ring-offset-2 focus-visible:ring-offset-fd-background active:scale-[0.98]",
+              isAskAIHintActive &&
+                "border-[#76f4f24d] shadow-[0_20px_34px_-16px_rgba(0,0,0,0.34),0_0_26px_-6px_rgba(118,244,242,0.22),0_0_0_1px_rgba(118,244,242,0.16)]",
+            )}
             title="Ask AI (Cmd/Ctrl+I)"
             aria-label="Ask AI"
           >
-            <MessageCircle className="size-4" strokeWidth={1.8} />
-            <span>Ask AI</span>
-            <span className="pointer-events-none absolute left-1/2 top-full z-10 mt-2 inline-flex -translate-x-1/2 translate-y-1 items-center gap-1 opacity-0 transition-all duration-150 group-hover:-translate-x-1/2 group-hover:translate-y-0 group-hover:opacity-100 group-focus-visible:-translate-x-1/2 group-focus-visible:translate-y-0 group-focus-visible:opacity-100">
+            <span
+              aria-hidden="true"
+              className="ask-ai-button-shimmer pointer-events-none absolute inset-0 rounded-full overflow-hidden"
+            />
+            <MessageCircle className="relative z-10 size-4" strokeWidth={1.8} />
+            <span className="relative z-10">Ask AI</span>
+            <span className="pointer-events-none absolute left-1/2 top-full z-20 mt-2 inline-flex -translate-x-1/2 translate-y-1 items-center gap-1 opacity-0 transition-all duration-150 group-hover:-translate-x-1/2 group-hover:translate-y-0 group-hover:opacity-100 group-focus-visible:-translate-x-1/2 group-focus-visible:translate-y-0 group-focus-visible:opacity-100">
               <kbd className="inline-flex min-w-5 items-center justify-center rounded border border-fd-border/80 bg-fd-secondary px-1.5 py-0.5 font-mono text-[11px] text-fd-muted-foreground shadow-sm">
                 ⌘
               </kbd>
diff --git a/src/styles/app.css b/src/styles/app.css
index cec29db..54971b2 100644
--- a/src/styles/app.css
+++ b/src/styles/app.css
@@ -55,6 +55,48 @@
   display: none;
 }
 
+@keyframes ask-ai-empty-shimmer {
+  0% {
+    transform: translateX(-140%);
+  }
+  100% {
+    transform: translateX(140%);
+  }
+}
+
+.ask-ai-button-shimmer::after {
+  content: "";
+  position: absolute;
+  inset: -1px;
+  border-radius: inherit;
+  pointer-events: none;
+  background:
+    linear-gradient(
+      112deg,
+      transparent 0%,
+      transparent 38%,
+      rgba(118, 244, 242, 0.04) 46%,
+      rgba(118, 244, 242, 0.22) 50%,
+      rgba(118, 244, 242, 0.04) 54%,
+      transparent 62%,
+      transparent 100%
+    );
+  transform: translateX(-140%);
+  opacity: 0;
+  transition: opacity 220ms ease;
+}
+
+.ask-ai-button[data-ai-hint="true"] .ask-ai-button-shimmer::after {
+  opacity: 1;
+  animation: ask-ai-empty-shimmer 1.85s ease-in-out infinite;
+}
+
+@media (prefers-reduced-motion: reduce) {
+  .ask-ai-button[data-ai-hint="true"] .ask-ai-button-shimmer::after {
+    animation: none;
+  }
+}
+
 /* Fix mobile dropdown icon sizing - make SVGs fill their container.
    The popover renders via a Radix portal at <body>, not inside #nd-sidebar,
    so we target both the sidebar trigger and the portal popover separately.