diff --git a/apps/web/src/components/payments/PlanDetails.tsx b/apps/web/src/components/payments/PlanDetails.tsx
index 2590e165..4b4c43bb 100644
--- a/apps/web/src/components/payments/PlanDetails.tsx
+++ b/apps/web/src/components/payments/PlanDetails.tsx
@@ -1,5 +1,6 @@
 import { Plan } from "@prisma/client";
 import { PLAN_PERKS } from "~/lib/constants/payments";
+import { isEntitledSubscriptionStatus } from "~/lib/subscription-status";
 import { CheckCircle2 } from "lucide-react";
 import { api } from "~/trpc/react";
 import Spinner from "@usesend/ui/src/spinner";
@@ -17,13 +18,14 @@ export const PlanDetails = () => {
 
   const planKey = currentTeam.plan as keyof typeof PLAN_PERKS;
   const perks = PLAN_PERKS[planKey] || [];
+  const isEntitled = isEntitledSubscriptionStatus(
+    subscriptionQuery.data?.status,
+  );
 
   return (
     <div>
       <div className="capitalize text-lg">
-        {subscriptionQuery.data?.status === "active"
-          ? planKey.toLowerCase()
-          : "free"}
+        {isEntitled ? planKey.toLowerCase() : "free"}
       </div>
       <div className="flex items-center gap-2">
         <div className="text-muted-foreground text-sm">Current plan</div>
diff --git a/apps/web/src/lib/subscription-status.ts b/apps/web/src/lib/subscription-status.ts
new file mode 100644
index 00000000..311a60d6
--- /dev/null
+++ b/apps/web/src/lib/subscription-status.ts
@@ -0,0 +1,11 @@
+const ENTITLED_SUBSCRIPTION_STATUSES = new Set([
+  "active",
+  "trialing",
+  "past_due",
+]);
+
+export function isEntitledSubscriptionStatus(
+  status: string | null | undefined,
+) {
+  return Boolean(status && ENTITLED_SUBSCRIPTION_STATUSES.has(status));
+}
diff --git a/apps/web/src/lib/subscription-status.unit.test.ts b/apps/web/src/lib/subscription-status.unit.test.ts
new file mode 100644
index 00000000..ddbc9240
--- /dev/null
+++ b/apps/web/src/lib/subscription-status.unit.test.ts
@@ -0,0 +1,20 @@
+import { describe, expect, it } from "vitest";
+import { isEntitledSubscriptionStatus } from "~/lib/subscription-status";
+
+describe("isEntitledSubscriptionStatus", () => {
+  it("treats retrying subscriptions as entitled", () => {
+    expect(isEntitledSubscriptionStatus("past_due")).toBe(true);
+  });
+
+  it("treats active and trialing subscriptions as entitled", () => {
+    expect(isEntitledSubscriptionStatus("active")).toBe(true);
+    expect(isEntitledSubscriptionStatus("trialing")).toBe(true);
+  });
+
+  it("treats exhausted or incomplete subscriptions as not entitled", () => {
+    expect(isEntitledSubscriptionStatus("unpaid")).toBe(false);
+    expect(isEntitledSubscriptionStatus("canceled")).toBe(false);
+    expect(isEntitledSubscriptionStatus("incomplete")).toBe(false);
+    expect(isEntitledSubscriptionStatus(null)).toBe(false);
+  });
+});
diff --git a/apps/web/src/server/billing/payments.ts b/apps/web/src/server/billing/payments.ts
index 00459e31..a73fd04f 100644
--- a/apps/web/src/server/billing/payments.ts
+++ b/apps/web/src/server/billing/payments.ts
@@ -1,5 +1,6 @@
 import Stripe from "stripe";
 import { env } from "~/env";
+import { isEntitledSubscriptionStatus } from "~/lib/subscription-status";
 import { db } from "../db";
 import { sendSubscriptionConfirmationEmail } from "../mailer";
 import { TeamService } from "../service/team-service";
@@ -149,6 +150,7 @@ export async function syncStripeData(customerId: string) {
     .filter((id): id is string => Boolean(id));
 
   const nextPlan = getPlanFromPriceIds(priceIds);
+  const isEntitled = isEntitledSubscriptionStatus(subscription.status);
   const isNowPaid = subscription.status === "active" && nextPlan !== "FREE";
   const shouldSendSubscriptionConfirmation = !wasPaid && isNowPaid;
 
@@ -159,10 +161,10 @@ export async function syncStripeData(customerId: string) {
       priceId: subscription.items.data[0]?.price?.id || "",
       priceIds: priceIds,
       currentPeriodEnd: new Date(
-        subscription.items.data[0]?.current_period_end * 1000
+        subscription.items.data[0]?.current_period_end * 1000,
       ),
       currentPeriodStart: new Date(
-        subscription.items.data[0]?.current_period_start * 1000
+        subscription.items.data[0]?.current_period_start * 1000,
       ),
       cancelAtPeriodEnd: subscription.cancel_at
         ? new Date(subscription.cancel_at * 1000)
@@ -176,10 +178,10 @@ export async function syncStripeData(customerId: string) {
       priceId: subscription.items.data[0]?.price?.id || "",
       priceIds: priceIds,
       currentPeriodEnd: new Date(
-        subscription.items.data[0]?.current_period_end * 1000
+        subscription.items.data[0]?.current_period_end * 1000,
       ),
       currentPeriodStart: new Date(
-        subscription.items.data[0]?.current_period_start * 1000
+        subscription.items.data[0]?.current_period_start * 1000,
       ),
       cancelAtPeriodEnd: subscription.cancel_at
         ? new Date(subscription.cancel_at * 1000)
@@ -191,7 +193,7 @@ export async function syncStripeData(customerId: string) {
 
   await TeamService.updateTeam(team.id, {
     plan: subscription.status === "canceled" ? "FREE" : nextPlan,
-    isActive: subscription.status === "active",
+    isActive: isEntitled,
   });
 
   if (shouldSendSubscriptionConfirmation) {
@@ -201,12 +203,12 @@ export async function syncStripeData(customerId: string) {
         teamUsers
           .map((tu) => tu.user?.email)
           .filter((email): email is string => Boolean(email))
-          .map((email) => sendSubscriptionConfirmationEmail(email))
+          .map((email) => sendSubscriptionConfirmationEmail(email)),
       );
     } catch (err) {
       logger.error(
         { err, teamId: team.id },
-        "[Billing]: Failed sending subscription confirmation email"
+        "[Billing]: Failed sending subscription confirmation email",
       );
     }
   }