diff --git a/api/src/routes/checkout.ts b/api/src/routes/checkout.ts
index c36617e..ce3ed0a 100644
--- a/api/src/routes/checkout.ts
+++ b/api/src/routes/checkout.ts
@@ -929,6 +929,22 @@ router.post("/api/v1/checkout/create-session", async (req, res) => {
         );
       }
       console.log(`[checkout] $0 order — skipping payment for ${order_type} ${order_id} (discount ${discount_cents} >= base ${base_cents})`);
+
+      // Send intake/confirmation email for free compliance orders (normally triggered by Stripe webhook)
+      if (order_type === "compliance_batch" || order_type === "compliance") {
+        try {
+          const { rows: updatedOrders } = await pool.query(
+            `SELECT * FROM compliance_orders WHERE ${order_type === "compliance_batch" ? "batch_id" : "order_number"} = $1`,
+            [order_id],
+          );
+          if (updatedOrders.length > 0) {
+            await sendComplianceIntakeEmail(order_id, order_type, updatedOrders);
+          }
+        } catch (emailErr) {
+          console.error("[checkout] Free order intake email failed (non-fatal):", emailErr);
+        }
+      }
+
       res.json({
         checkout_url: `${DOMAIN}/order/success?order_id=${order_id}&order_type=${order_type}&free=1`,
         session_id: null,