diff --git a/apps/web/src/server/billing/payments.ts b/apps/web/src/server/billing/payments.ts
index 41cec92..00459e3 100644
--- a/apps/web/src/server/billing/payments.ts
+++ b/apps/web/src/server/billing/payments.ts
@@ -1,7 +1,9 @@
 import Stripe from "stripe";
 import { env } from "~/env";
 import { db } from "../db";
+import { sendSubscriptionConfirmationEmail } from "../mailer";
 import { TeamService } from "../service/team-service";
+import { logger } from "../logger/log";
 
 export function getStripe() {
   if (!env.STRIPE_SECRET_KEY) {
@@ -123,6 +125,8 @@ export async function syncStripeData(customerId: string) {
     return;
   }
 
+  const wasPaid = team.isActive && team.plan !== "FREE";
+
   const subscriptions = await stripe.subscriptions.list({
     customer: customerId,
     limit: 1,
@@ -144,6 +148,10 @@ export async function syncStripeData(customerId: string) {
     .map((item) => item.price?.id)
     .filter((id): id is string => Boolean(id));
 
+  const nextPlan = getPlanFromPriceIds(priceIds);
+  const isNowPaid = subscription.status === "active" && nextPlan !== "FREE";
+  const shouldSendSubscriptionConfirmation = !wasPaid && isNowPaid;
+
   await db.subscription.upsert({
     where: { id: subscription.id },
     update: {
@@ -182,10 +190,24 @@ export async function syncStripeData(customerId: string) {
   });
 
   await TeamService.updateTeam(team.id, {
-    plan:
-      subscription.status === "canceled"
-        ? "FREE"
-        : getPlanFromPriceIds(priceIds),
+    plan: subscription.status === "canceled" ? "FREE" : nextPlan,
     isActive: subscription.status === "active",
   });
+
+  if (shouldSendSubscriptionConfirmation) {
+    try {
+      const teamUsers = await TeamService.getTeamUsers(team.id);
+      await Promise.all(
+        teamUsers
+          .map((tu) => tu.user?.email)
+          .filter((email): email is string => Boolean(email))
+          .map((email) => sendSubscriptionConfirmationEmail(email))
+      );
+    } catch (err) {
+      logger.error(
+        { err, teamId: team.id },
+        "[Billing]: Failed sending subscription confirmation email"
+      );
+    }
+  }
 }
diff --git a/apps/web/src/server/mailer.ts b/apps/web/src/server/mailer.ts
index 2a7f843..bc360e6 100644
--- a/apps/web/src/server/mailer.ts
+++ b/apps/web/src/server/mailer.ts
@@ -69,6 +69,19 @@ export async function sendTeamInviteEmail(
   await sendMail(email, subject, text, html);
 }
 
+export async function sendSubscriptionConfirmationEmail(email: string) {
+  if (!env.FOUNDER_EMAIL) {
+    logger.error("FOUNDER_EMAIL not configured");
+    return;
+  }
+
+  const subject = "Thanks for subscribing to useSend";
+  const text = `Hey,\n\nThanks for subscribing to useSend, just wanted to let you know you can join the discord server to have a dedicated support channel for your team. So that we can address your queries / bugs asap.\n\nYou can join over using the link: https://discord.com/invite/BU8n8pJv8S\n\nIf you prefer slack, please let me know\n\ncheers,\nkoushik - useSend`;
+  const html = text.replace(/\n/g, "<br />");
+
+  await sendMail(email, subject, text, html, undefined, env.FOUNDER_EMAIL);
+}
+
 export async function sendMail(
   email: string,
   subject: string,
diff --git a/apps/web/src/server/service/team-service.ts b/apps/web/src/server/service/team-service.ts
index b268eff..596ce51 100644
--- a/apps/web/src/server/service/team-service.ts
+++ b/apps/web/src/server/service/team-service.ts
@@ -563,6 +563,7 @@ export class TeamService {
       "[TeamService]: Set warning notification cooldown"
     );
   }
+
 }
 
 async function getLimitReachedEmail(