diff --git a/apps/pay/src/routes.ts b/apps/pay/src/routes.ts
index 3acc289..5430bb2 100644
--- a/apps/pay/src/routes.ts
+++ b/apps/pay/src/routes.ts
@@ -74,7 +74,14 @@ export const routes = new Elysia()
     // Calculate amount
     const planDef = PLANS[plan];
     if (!planDef) { set.status = 400; return { error: `Unknown plan: ${plan}` }; }
-    const amountUsd = planDef.priceUsd ?? (planDef.monthlyUsd! * (months ?? 1));
+    let amountUsd = planDef.priceUsd ?? (planDef.monthlyUsd! * (months ?? 1));
+
+    // Lifetime discount: credit up to 50% of lifetime price from previous payments
+    if (plan === "lifetime" && planDef.priceUsd) {
+      const [{ total }] = await sql`SELECT COALESCE(SUM(amount_usd), 0)::numeric as total FROM payments WHERE account_id = ${accountId} AND status = 'paid'`;
+      const credit = Math.min(Number(total), planDef.priceUsd * 0.5);
+      amountUsd = Math.max(amountUsd - credit, 1);
+    }
     const rates = await getExchangeRates();
     const rate = rates[coin];
     if (!rate) { set.status = 500; return { error: "Could not fetch exchange rate" }; }
diff --git a/apps/web/src/routes/dashboard.ts b/apps/web/src/routes/dashboard.ts
index 3f0237b..90a2ca3 100644
--- a/apps/web/src/routes/dashboard.ts
+++ b/apps/web/src/routes/dashboard.ts
@@ -273,6 +273,9 @@ export const dashboard = new Elysia()
     const [acc] = await sql`SELECT plan, plan_expires_at FROM accounts WHERE id = ${resolved.accountId}`;
     if (acc.plan === "lifetime") return redirect("/dashboard/settings");
 
+    // Total spent on paid invoices (for lifetime discount)
+    const [{ total_spent }] = await sql`SELECT COALESCE(SUM(amount_usd), 0)::numeric as total_spent FROM payments WHERE account_id = ${resolved.accountId} AND status = 'paid'`;
+
     // Fetch coins server-side for no-JS rendering
     const payApi = process.env.PAY_API || "https://pay.pingql.com";
     let coins: any[] = [];
@@ -282,7 +285,7 @@ export const dashboard = new Elysia()
       coins = data.coins || [];
     } catch {}
 
-    return html("checkout", { nav: "settings", account: acc, payApi, invoiceId: null, coins, invoice: null });
+    return html("checkout", { nav: "settings", account: acc, payApi, invoiceId: null, coins, invoice: null, totalSpent: Number(total_spent) });
   })
 
   // Existing invoice by ID — SSR the payment status
diff --git a/apps/web/src/views/checkout.ejs b/apps/web/src/views/checkout.ejs
index 569aa14..f5c48fa 100644
--- a/apps/web/src/views/checkout.ejs
+++ b/apps/web/src/views/checkout.ejs
@@ -6,6 +6,10 @@
   const coins = it.coins || [];
   const invoice = it.invoice;
   const payApi = it.payApi || '';
+  const totalSpent = it.totalSpent || 0;
+  const lifetimeBase = 140;
+  const lifetimeDiscount = Math.min(totalSpent, lifetimeBase * 0.5);
+  const lifetimePrice = lifetimeBase - lifetimeDiscount;
 %>
 
 <style>
@@ -44,9 +48,18 @@
       </label>
       <label for="plan-lifetime"
         class="cursor-pointer text-left bg-surface border-2 border-border-subtle hover:border-yellow-500/40 rounded-xl p-5 transition-colors relative">
+        <% if (lifetimeDiscount > 0) { %>
+        <span class="absolute top-3 right-3 text-[10px] font-semibold px-2 py-0.5 rounded-full bg-green-500/15 text-green-400 border border-green-500/20">Loyalty Discount</span>
+        <% } else { %>
         <span class="absolute top-3 right-3 text-[10px] font-semibold px-2 py-0.5 rounded-full bg-yellow-500/15 text-yellow-500 border border-yellow-500/20">Launch Deal</span>
+        <% } %>
         <div class="text-xs text-yellow-500/70 uppercase tracking-wider font-mono mb-1">Lifetime</div>
-        <div class="text-2xl font-bold text-gray-100">$140</div>
+        <% if (lifetimeDiscount > 0) { %>
+        <div class="text-2xl font-bold text-gray-100">$<%= lifetimePrice.toFixed(0) %> <span class="text-sm font-normal text-gray-600 line-through">$<%= lifetimeBase %></span></div>
+        <div class="text-xs text-green-400/70 mt-1">You've paid us $<%= totalSpent.toFixed(0) %> — we've credited $<%= lifetimeDiscount.toFixed(0) %> toward lifetime</div>
+        <% } else { %>
+        <div class="text-2xl font-bold text-gray-100">$<%= lifetimeBase %></div>
+        <% } %>
         <div class="text-xs text-gray-500 mt-2">One-time, 200 monitors forever</div>
       </label>
     </div>