diff --git a/api/src/routes/checkout.ts b/api/src/routes/checkout.ts
index ce8e4df..c36617e 100644
--- a/api/src/routes/checkout.ts
+++ b/api/src/routes/checkout.ts
@@ -645,6 +645,36 @@ router.post("/api/v1/checkout/create-session", async (req, res) => {
       throw err;
     }
     if (!orderData) {
+      // Check if the order exists but is already paid (e.g. free order, duplicate submit)
+      try {
+        const tables: Record<string, {table: string; col: string}> = {
+          canada_crtc: { table: "canada_crtc_orders", col: "order_number" },
+          formation: { table: "formation_orders", col: "order_number" },
+          bundle: { table: "bundle_orders", col: "order_number" },
+          compliance: { table: "compliance_orders", col: "order_number" },
+          compliance_batch: { table: "compliance_orders", col: "batch_id" },
+        };
+        const t = tables[order_type];
+        if (t) {
+          const { rows } = await pool.query(
+            `SELECT payment_status, payment_method FROM ${t.table} WHERE ${t.col} = $1 LIMIT 1`,
+            [order_id],
+          );
+          if (rows.length > 0 && rows[0].payment_status === "paid") {
+            // Already paid — redirect to success
+            const isFree = rows[0].payment_method === "free";
+            console.log(`[checkout] Order ${order_id} already paid (${rows[0].payment_method}) — returning success redirect`);
+            res.json({
+              checkout_url: `${DOMAIN}/order/success?order_id=${order_id}&order_type=${order_type}${isFree ? "&free=1" : ""}`,
+              session_id: null,
+              total_cents: 0,
+              surcharge_cents: 0,
+              surcharge_pct: 0,
+            });
+            return;
+          }
+        }
+      } catch { /* fall through to 404 */ }
       res.status(404).json({ error: "Order not found or not in pending_payment state" });
       return;
     }