diff --git a/src/components/SasquatchGuide.tsx b/src/components/SasquatchGuide.tsx
index ef84a5f..a7b192f 100644
--- a/src/components/SasquatchGuide.tsx
+++ b/src/components/SasquatchGuide.tsx
@@ -438,17 +438,31 @@ const STATIC_FAQ: Record<string, string> = {
   'what relay': "SkateSpots uses: 🛹 goskatespots.nostr1.com (primary, allowlisted for quality) + relay.ditto.pub (global) + purplepag.es (profile aggregator). Your data is replicated across all of them for redundancy.",
   'trip planner': "Tell me a city and I'll build a day-by-day skate trip 🗺️ — spots, events, coaches and local crews, weather-aware (rainy day = crew tip for covered spots). Try 'plan me 3 days in Lisbon'. I can save it all to a Collection, and hand you off to flights/stays on the real sites (no KYC, no middleman). 🛹",
   'plan a trip': "Just say 'plan me 3 days in Barcelona' (or any city) and I'll map out spots, sessions, coaches and local crews for each day. Save it as a Collection and go shred. 🗺️🛹",
+  // ── Sasquatch Pro — answered locally so it never depends on the AI brain ──
+  'sasquatch pro': "**Sasquatch Pro** 🦧⚡ is a Lightning supporter pass that unlocks the personal side of me:\n\n• 🧠 **Personal assistant** — I know your Stash, crews, spots & listings\n• ✨ **Action drafts** — list gear, post a spot status, plan trips (you always confirm before anything publishes)\n• 🚀 **Priority AI** — better model, higher limits, longer memory\n• 🌤️ **Proactive nudges** — weather + spot tips (opt-in)\n• 🏅 **Supporter badge** + Pro-only skins\n\nFree Sasquatch stays free: public spot/event/coach/crew search, the glossary & trip planning all work without Pro. Pro just adds the *personal* stuff and keeps SkateSpots ad-free. Tap **⚡ Go Pro** up top. Tiers: 7 days ~2k sats, 1 month ~5k, 3 months ~12k, 1 year ~36k.",
+  'pro perks': "Pro perks 🦧⚡: personal assistant (reads your Stash/crews/spots/listings), action drafts (list gear, post status, plan trips — you confirm), priority AI model with higher limits & longer memory, opt-in weather/spot nudges, and a supporter badge + Pro skins. Free stays free — Pro adds the personal layer & keeps the app ad-free. Tap **⚡ Go Pro** up top.",
+  'pro version': "The Pro version of me 🦧⚡ adds a **personal assistant**: I can read your Stash, crews, spots & listings, and draft actions for you (list gear, post a status, plan a trip — you always confirm first). Plus a priority AI model, higher limits, longer memory, opt-in weather nudges, and a supporter badge. Free Sasquatch (spot/event/coach/crew search, glossary, trip planner) stays free. Tap **⚡ Go Pro** up top.",
+  'perks': "Pro perks 🦧⚡: personal assistant (your Stash/crews/spots/listings), action drafts you confirm, priority AI + higher limits + longer memory, opt-in weather/spot nudges, and a supporter badge + Pro skins. Tap **⚡ Go Pro** up top.",
+  'go pro': "Tap the **⚡ Go Pro** button up top to open the upgrade sheet. Pro unlocks my personal assistant (Stash/crews/spots/listings), action drafts, priority AI and a supporter badge. Pay with Lightning — 7 days ~2k sats up to 1 year ~36k sats. Free features stay free. 🦧",
+  'pro pricing': "Pro tiers (pay with Lightning ⚡): **7 days** ~2,000 sats (~$1.20), **1 month** ~5,000 sats (~$3), **3 months** ~12,000 sats (~$7, 20% off), **1 year** ~36,000 sats (~$21, best value). Tap **⚡ Go Pro** up top.",
+  'how much is pro': "Pro tiers: 7 days ~2,000 sats, 1 month ~5,000 sats, 3 months ~12,000 sats (20% off), 1 year ~36,000 sats (best value). Pay with Lightning ⚡. Tap **⚡ Go Pro** up top.",
+  'upgrade': "To upgrade to Sasquatch Pro, tap the **⚡ Go Pro** button up top. Pay with Lightning (7 days ~2k sats up to 1 year ~36k). Pro unlocks my personal assistant, action drafts, priority AI and a supporter badge. 🦧⚡",
 };
 
 function getStaticAnswer(question: string): string | null {
   const q = question.toLowerCase().trim();
   // Exact match first (for greetings like "hi", "hey")
   if (STATIC_FAQ[q]) return STATIC_FAQ[q];
-  // Then partial match
+
+  // Partial match — prefer the LONGEST matching key so specific phrases
+  // ("sasquatch pro", "pro pricing") win over broad ones ("pro", "perks").
+  let best: { key: string; answer: string } | null = null;
   for (const [key, answer] of Object.entries(STATIC_FAQ)) {
-    if (q.includes(key)) return answer;
+    if (q.includes(key) && (!best || key.length > best.key.length)) {
+      best = { key, answer };
+    }
   }
-  return null;
+  return best?.answer ?? null;
 }
 
 // ─── CVM connection status indicator ─────────────────────────────────────────
diff --git a/src/components/SasquatchProDialog.tsx b/src/components/SasquatchProDialog.tsx
index e97806a..39df138 100644
--- a/src/components/SasquatchProDialog.tsx
+++ b/src/components/SasquatchProDialog.tsx
@@ -75,7 +75,7 @@ export function SasquatchProDialog({
   // Toast + close on success.
   useEffect(() => {
     if (purchase.state === 'paid') {
-      toast({ title: 'Welcome to Sasquatch Pro! 🦧⚡', description: 'Your supporter pass is active. Thanks for keeping the streets free.' });
+      toast({ title: 'Welcome to Sasquatch Pro! 🦧⚡', description: 'Your pass is active — a receipt just landed in your DMs. Thanks for keeping the streets free.' });
       const t = setTimeout(() => { onOpenChange(false); purchase.reset(); }, 1400);
       return () => clearTimeout(t);
     }
diff --git a/src/hooks/usePurchasePro.ts b/src/hooks/usePurchasePro.ts
index 836fc93..c91cb9a 100644
--- a/src/hooks/usePurchasePro.ts
+++ b/src/hooks/usePurchasePro.ts
@@ -21,6 +21,7 @@ import { useCurrentUser } from '@/hooks/useCurrentUser';
 import { useNWC } from '@/hooks/useNWCContext';
 import { useWallet } from '@/hooks/useWallet';
 import { useAppContext } from '@/hooks/useAppContext';
+import { useSendDirectMessage } from '@/hooks/useDirectMessages';
 import { PLATFORM_OWNER_PUBKEYS } from '@/hooks/useListingRestrictions';
 import {
   getZapProviderPubkey,
@@ -47,9 +48,45 @@ export function usePurchasePro() {
   const { getActiveConnection, sendPayment } = useNWC();
   const { webln } = useWallet();
   const { config } = useAppContext();
+  const { mutateAsync: sendDM } = useSendDirectMessage();
 
   const [result, setResult] = useState<PurchaseResult>({ invoice: null, state: 'idle', error: null });
 
+  /**
+   * Send the buyer an encrypted (NIP-17) confirmation to their own inbox — a
+   * durable, private receipt of what they bought. Best-effort: a failure here
+   * never blocks the purchase (they already paid + got the on-relay receipt).
+   */
+  const sendConfirmationDM = useCallback(
+    async (tier: ProTier, expiry: number) => {
+      if (!user?.pubkey || !user.signer?.nip44) return;
+      const until = new Date(expiry * 1000).toLocaleDateString(undefined, {
+        year: 'numeric', month: 'long', day: 'numeric',
+      });
+      const content = [
+        `🦧⚡ Sasquatch Pro — you're in!`,
+        ``,
+        `Pass: ${tier.label} (${tier.sats.toLocaleString()} sats)`,
+        `Active until: ${until}`,
+        ``,
+        `What you unlocked:`,
+        `• Personal assistant — I read your Stash, crews, spots & listings`,
+        `• Action drafts — list gear, post a spot status, plan trips (you confirm)`,
+        `• Priority AI model, higher limits & longer memory`,
+        `• Opt-in weather + spot nudges`,
+        `• ⚡ Supporter badge + Pro-only skins`,
+        ``,
+        `Thanks for keeping SkateSpots free & ad-free. Now go shred. 🛹`,
+      ].join('\n');
+      try {
+        await sendDM({ recipients: user.pubkey, content, subject: 'Sasquatch Pro receipt' });
+      } catch {
+        /* best-effort — don't fail the purchase over a receipt DM */
+      }
+    },
+    [user, sendDM],
+  );
+
   /** Publish the self-signed fallback receipt for a paid tier. */
   const publishReceipt = useCallback(
     async (tier: ProTier, expiry: number) => {
@@ -125,6 +162,7 @@ export function usePurchasePro() {
           try {
             await sendPayment(nwc, invoice);
             await publishReceipt(tier, expiry);
+            await sendConfirmationDM(tier, expiry);
             setResult({ invoice: null, state: 'paid', error: null });
             return;
           } catch {
@@ -137,6 +175,7 @@ export function usePurchasePro() {
             if (typeof webln.enable === 'function') await webln.enable();
             await webln.sendPayment(invoice);
             await publishReceipt(tier, expiry);
+            await sendConfirmationDM(tier, expiry);
             setResult({ invoice: null, state: 'paid', error: null });
             return;
           } catch {
@@ -155,7 +194,7 @@ export function usePurchasePro() {
         });
       }
     },
-    [user, config, getActiveConnection, sendPayment, webln, publishReceipt],
+    [user, config, getActiveConnection, sendPayment, webln, publishReceipt, sendConfirmationDM],
   );
 
   /** Called after a manual (QR) payment to record the pass locally. */
@@ -164,6 +203,7 @@ export function usePurchasePro() {
       const expiry = Math.floor(Date.now() / 1000) + tier.days * DAY_SECONDS;
       try {
         await publishReceipt(tier, expiry);
+        await sendConfirmationDM(tier, expiry);
         setResult({ invoice: null, state: 'paid', error: null });
       } catch (err) {
         setResult({
@@ -173,7 +213,7 @@ export function usePurchasePro() {
         });
       }
     },
-    [publishReceipt],
+    [publishReceipt, sendConfirmationDM],
   );
 
   const reset = useCallback(() => setResult({ invoice: null, state: 'idle', error: null }), []);
diff --git a/src/lib/sasquatchBrain.ts b/src/lib/sasquatchBrain.ts
index f1a33cc..485457a 100644
--- a/src/lib/sasquatchBrain.ts
+++ b/src/lib/sasquatchBrain.ts
@@ -14,6 +14,9 @@ const OPENROUTER_URL = 'https://openrouter.ai/api/v1/chat/completions';
 // rate-limited (429) we back off briefly then move to the next model.
 export const FREE_MODELS = [
   'meta-llama/llama-3.3-70b-instruct:free',
+  'deepseek/deepseek-chat-v3-0324:free',
+  'google/gemini-2.0-flash-exp:free',
+  'qwen/qwen-2.5-72b-instruct:free',
   'google/gemma-2-9b-it:free',
   'mistralai/mistral-7b-instruct:free',
   'qwen/qwen-2.5-7b-instruct:free',