diff --git a/packages/api/src/router/stripe/webhook.ts b/packages/api/src/router/stripe/webhook.ts
index d37d6238..e73353e9 100644
--- a/packages/api/src/router/stripe/webhook.ts
+++ b/packages/api/src/router/stripe/webhook.ts
@@ -244,8 +244,14 @@ export const webhookRouter = createTRPCRouter({
       return;
     }
 
-    const { _workspace, memberEmails } = await opts.ctx.db.transaction(
+    const { _workspace, memberEmails, oldPlan } = await opts.ctx.db.transaction(
       async (tx) => {
+        const existing = await tx
+          .select({ plan: workspace.plan })
+          .from(workspace)
+          .where(eq(workspace.stripeId, customerId))
+          .get();
+
         const _workspace = await tx
           .update(workspace)
           .set({
@@ -355,6 +361,7 @@ export const webhookRouter = createTRPCRouter({
           memberEmails: members
             .map((m) => m.email)
             .filter((email): email is string => Boolean(email)),
+          oldPlan: existing?.plan ?? "free",
         };
       },
     );
@@ -368,11 +375,15 @@ export const webhookRouter = createTRPCRouter({
 
     const workspaceId = _workspace[0].id;
 
-    await emailClient.sendPlanDowngrade({
-      to: memberEmails,
-      workspaceName: _workspace[0].name,
-      newPlan: "free",
-    });
+    // Stripe can redeliver the event; only notify on an actual plan change
+    if (oldPlan !== "free") {
+      await emailClient.sendPlanDowngrade({
+        to: memberEmails,
+        workspaceName: _workspace[0].name,
+        oldPlan,
+        newPlan: "free",
+      });
+    }
 
     const customer = await stripe.customers.retrieve(customerId);
 
diff --git a/packages/emails/src/client.tsx b/packages/emails/src/client.tsx
index 3fabd77e..23991feb 100644
--- a/packages/emails/src/client.tsx
+++ b/packages/emails/src/client.tsx
@@ -282,6 +282,7 @@ export class EmailClient {
       const result = await this.client.batch.send(
         recipients.map((member) => ({
           from: "OpenStatus <notifications@notifications.openstatus.dev>",
+          replyTo: "Thibault Le Ouay Ducasse <thibault@openstatus.dev>",
           subject: `Your workspace has been downgraded to the ${req.newPlan} plan`,
           to: member,
           html,