diff --git a/app/api/webhooks/stripe/__tests__/routeTestMocks.ts b/app/api/webhooks/stripe/__tests__/routeTestMocks.ts
index 34260da3c..a5fca8825 100644
--- a/app/api/webhooks/stripe/__tests__/routeTestMocks.ts
+++ b/app/api/webhooks/stripe/__tests__/routeTestMocks.ts
@@ -15,3 +15,19 @@ vi.mock("@/lib/stripe/processCreditsTopupSession", () => ({
 vi.mock("@/lib/stripe/processCreditsTopupPaymentIntent", () => ({
   processCreditsTopupPaymentIntent: vi.fn(),
 }));
+
+vi.mock("@/lib/stripe/processSubscriptionCreated", () => ({
+  processSubscriptionCreated: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/processSubscriptionTrialWillEnd", () => ({
+  processSubscriptionTrialWillEnd: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/processSubscriptionUpdated", () => ({
+  processSubscriptionUpdated: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/processSubscriptionDeleted", () => ({
+  processSubscriptionDeleted: vi.fn(),
+}));
diff --git a/lib/stripe/__tests__/buildSubscriptionSalesContext.test.ts b/lib/stripe/__tests__/buildSubscriptionSalesContext.test.ts
new file mode 100644
index 000000000..fa0433472
--- /dev/null
+++ b/lib/stripe/__tests__/buildSubscriptionSalesContext.test.ts
@@ -0,0 +1,62 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import type Stripe from "stripe";
+
+const { getCustomerEmailMock, getLtvMock } = vi.hoisted(() => ({
+  getCustomerEmailMock: vi.fn(),
+  getLtvMock: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/getCustomerEmail", () => ({ getCustomerEmail: getCustomerEmailMock }));
+vi.mock("@/lib/stripe/getCustomerLifetimeValue", () => ({
+  getCustomerLifetimeValue: getLtvMock,
+}));
+
+const { buildSubscriptionSalesContext } = await import(
+  "@/lib/stripe/buildSubscriptionSalesContext"
+);
+
+const sub = (overrides: object = {}): Stripe.Subscription =>
+  ({
+    id: "sub_1",
+    customer: "cus_9",
+    items: {
+      data: [{ price: { unit_amount: 9900, recurring: { interval: "month" } } }],
+    },
+    ...overrides,
+  }) as unknown as Stripe.Subscription;
+
+describe("buildSubscriptionSalesContext", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    getCustomerEmailMock.mockResolvedValue("fan@example.com");
+    getLtvMock.mockResolvedValue(12345);
+  });
+
+  it("builds customer, plan, and lifetime lines from the subscription", async () => {
+    await expect(buildSubscriptionSalesContext(sub())).resolves.toEqual({
+      email: "fan@example.com",
+      customerLine: "Customer: fan@example.com (cus_9)",
+      planLine: "Plan: $99.00/month",
+      lifetimeLine: "Lifetime value: $123.45",
+    });
+    expect(getCustomerEmailMock).toHaveBeenCalledWith("cus_9");
+    expect(getLtvMock).toHaveBeenCalledWith("cus_9");
+  });
+
+  it("uses the id when the customer field is an expanded object", async () => {
+    const ctx = await buildSubscriptionSalesContext(sub({ customer: { id: "cus_9" } }));
+    expect(ctx.customerLine).toBe("Customer: fan@example.com (cus_9)");
+  });
+
+  it("falls back to the customer id when no email is found", async () => {
+    getCustomerEmailMock.mockResolvedValue(null);
+    const ctx = await buildSubscriptionSalesContext(sub());
+    expect(ctx.email).toBeNull();
+    expect(ctx.customerLine).toBe("Customer: cus_9");
+  });
+
+  it("tolerates a subscription without price data", async () => {
+    const ctx = await buildSubscriptionSalesContext(sub({ items: { data: [] } }));
+    expect(ctx.planLine).toBe("Plan: unknown");
+  });
+});
diff --git a/lib/stripe/__tests__/formatStripeTimestamp.test.ts b/lib/stripe/__tests__/formatStripeTimestamp.test.ts
new file mode 100644
index 000000000..4078f15f3
--- /dev/null
+++ b/lib/stripe/__tests__/formatStripeTimestamp.test.ts
@@ -0,0 +1,8 @@
+import { describe, it, expect } from "vitest";
+import { formatStripeTimestamp } from "@/lib/stripe/formatStripeTimestamp";
+
+describe("formatStripeTimestamp", () => {
+  it("formats a unix-seconds timestamp as an ISO date", () => {
+    expect(formatStripeTimestamp(1783415103)).toBe("2026-07-07");
+  });
+});
diff --git a/lib/stripe/__tests__/formatUsd.test.ts b/lib/stripe/__tests__/formatUsd.test.ts
new file mode 100644
index 000000000..c2a95b76a
--- /dev/null
+++ b/lib/stripe/__tests__/formatUsd.test.ts
@@ -0,0 +1,18 @@
+import { describe, it, expect } from "vitest";
+import { formatUsd } from "@/lib/stripe/formatUsd";
+
+describe("formatUsd", () => {
+  it("formats cents as dollars", () => {
+    expect(formatUsd(9900)).toBe("$99.00");
+    expect(formatUsd(546)).toBe("$5.46");
+    expect(formatUsd(500000)).toBe("$5000.00");
+  });
+
+  it("formats zero", () => {
+    expect(formatUsd(0)).toBe("$0.00");
+  });
+
+  it("formats negative amounts (net refunds)", () => {
+    expect(formatUsd(-150)).toBe("-$1.50");
+  });
+});
diff --git a/lib/stripe/__tests__/getCustomerEmail.test.ts b/lib/stripe/__tests__/getCustomerEmail.test.ts
new file mode 100644
index 000000000..764b46ae3
--- /dev/null
+++ b/lib/stripe/__tests__/getCustomerEmail.test.ts
@@ -0,0 +1,39 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+
+const { customersRetrieveMock } = vi.hoisted(() => ({ customersRetrieveMock: vi.fn() }));
+
+vi.mock("@/lib/stripe/client", () => ({
+  default: { customers: { retrieve: customersRetrieveMock } },
+}));
+
+const { getCustomerEmail } = await import("@/lib/stripe/getCustomerEmail");
+
+describe("getCustomerEmail", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    vi.spyOn(console, "error").mockImplementation(() => undefined);
+  });
+  afterEach(() => vi.mocked(console.error).mockRestore());
+
+  it("returns the email of a live customer", async () => {
+    customersRetrieveMock.mockResolvedValue({ id: "cus_1", email: "fan@example.com" });
+    await expect(getCustomerEmail("cus_1")).resolves.toBe("fan@example.com");
+    expect(customersRetrieveMock).toHaveBeenCalledWith("cus_1");
+  });
+
+  it("returns null for a deleted customer", async () => {
+    customersRetrieveMock.mockResolvedValue({ id: "cus_1", deleted: true });
+    await expect(getCustomerEmail("cus_1")).resolves.toBeNull();
+  });
+
+  it("returns null when the customer has no email", async () => {
+    customersRetrieveMock.mockResolvedValue({ id: "cus_1", email: null });
+    await expect(getCustomerEmail("cus_1")).resolves.toBeNull();
+  });
+
+  it("returns null and logs when the lookup fails", async () => {
+    customersRetrieveMock.mockRejectedValue(new Error("stripe down"));
+    await expect(getCustomerEmail("cus_1")).resolves.toBeNull();
+    expect(console.error).toHaveBeenCalled();
+  });
+});
diff --git a/lib/stripe/__tests__/getCustomerLifetimeValue.test.ts b/lib/stripe/__tests__/getCustomerLifetimeValue.test.ts
new file mode 100644
index 000000000..d83a2f530
--- /dev/null
+++ b/lib/stripe/__tests__/getCustomerLifetimeValue.test.ts
@@ -0,0 +1,59 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+
+const { chargesListMock } = vi.hoisted(() => ({ chargesListMock: vi.fn() }));
+
+vi.mock("@/lib/stripe/client", () => ({
+  default: { charges: { list: chargesListMock } },
+}));
+
+const { getCustomerLifetimeValue } = await import("@/lib/stripe/getCustomerLifetimeValue");
+
+const charge = (amount: number, amountRefunded = 0, status = "succeeded") => ({
+  amount,
+  amount_refunded: amountRefunded,
+  status,
+});
+
+describe("getCustomerLifetimeValue", () => {
+  beforeEach(() => vi.clearAllMocks());
+
+  it("sums succeeded charges in cents, net of refunds", async () => {
+    chargesListMock.mockResolvedValue({
+      data: [charge(9900), charge(546, 546), charge(2000, 500)],
+      has_more: false,
+    });
+
+    await expect(getCustomerLifetimeValue("cus_1")).resolves.toBe(9900 + 0 + 1500);
+    expect(chargesListMock).toHaveBeenCalledWith({ customer: "cus_1", limit: 100 });
+  });
+
+  it("ignores charges that did not succeed", async () => {
+    chargesListMock.mockResolvedValue({
+      data: [charge(9900, 0, "failed"), charge(546)],
+      has_more: false,
+    });
+
+    await expect(getCustomerLifetimeValue("cus_1")).resolves.toBe(546);
+  });
+
+  it("paginates until has_more is false", async () => {
+    chargesListMock
+      .mockResolvedValueOnce({
+        data: [charge(100), { ...charge(200), id: "ch_last" }],
+        has_more: true,
+      })
+      .mockResolvedValueOnce({ data: [charge(300)], has_more: false });
+
+    await expect(getCustomerLifetimeValue("cus_1")).resolves.toBe(600);
+    expect(chargesListMock).toHaveBeenNthCalledWith(2, {
+      customer: "cus_1",
+      limit: 100,
+      starting_after: "ch_last",
+    });
+  });
+
+  it("returns 0 for a customer with no charges", async () => {
+    chargesListMock.mockResolvedValue({ data: [], has_more: false });
+    await expect(getCustomerLifetimeValue("cus_1")).resolves.toBe(0);
+  });
+});
diff --git a/lib/stripe/__tests__/processSubscriptionCreated.test.ts b/lib/stripe/__tests__/processSubscriptionCreated.test.ts
new file mode 100644
index 000000000..de0ea9b1f
--- /dev/null
+++ b/lib/stripe/__tests__/processSubscriptionCreated.test.ts
@@ -0,0 +1,58 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import type Stripe from "stripe";
+
+const { buildContextMock, sendMock } = vi.hoisted(() => ({
+  buildContextMock: vi.fn(),
+  sendMock: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/buildSubscriptionSalesContext", () => ({
+  buildSubscriptionSalesContext: buildContextMock,
+}));
+vi.mock("@/lib/telegram/sendSalesNotification", () => ({ sendSalesNotification: sendMock }));
+
+const { processSubscriptionCreated } = await import("@/lib/stripe/processSubscriptionCreated");
+
+const CTX = {
+  email: "fan@example.com",
+  customerLine: "Customer: fan@example.com (cus_9)",
+  planLine: "Plan: $99.00/month",
+  lifetimeLine: "Lifetime value: $0.00",
+};
+
+const sub = (overrides: object = {}): Stripe.Subscription =>
+  ({
+    id: "sub_1",
+    customer: "cus_9",
+    status: "active",
+    ...overrides,
+  }) as unknown as Stripe.Subscription;
+
+describe("processSubscriptionCreated", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    buildContextMock.mockResolvedValue(CTX);
+  });
+
+  it("notifies a trial signup with the trial end date (new card on file)", async () => {
+    await processSubscriptionCreated(sub({ status: "trialing", trial_end: 1783415103 }));
+
+    expect(sendMock).toHaveBeenCalledTimes(1);
+    const { email, text } = sendMock.mock.calls[0][0];
+    expect(email).toBe("fan@example.com");
+    expect(text).toContain("New subscription (trial)");
+    expect(text).toContain("Customer: fan@example.com (cus_9)");
+    expect(text).toContain("Plan: $99.00/month");
+    expect(text).toContain("Trial ends: 2026-07-07");
+    expect(text).toContain("Lifetime value: $0.00");
+  });
+
+  it("notifies a direct (non-trial) subscription without a trial line", async () => {
+    await processSubscriptionCreated(sub());
+
+    const { text } = sendMock.mock.calls[0][0];
+    expect(text).toContain("New subscription");
+    expect(text).not.toContain("(trial)");
+    expect(text).not.toContain("Trial ends");
+  });
+});
diff --git a/lib/stripe/__tests__/processSubscriptionDeleted.test.ts b/lib/stripe/__tests__/processSubscriptionDeleted.test.ts
new file mode 100644
index 000000000..80644ac2a
--- /dev/null
+++ b/lib/stripe/__tests__/processSubscriptionDeleted.test.ts
@@ -0,0 +1,51 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import type Stripe from "stripe";
+
+const { buildContextMock, sendMock } = vi.hoisted(() => ({
+  buildContextMock: vi.fn(),
+  sendMock: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/buildSubscriptionSalesContext", () => ({
+  buildSubscriptionSalesContext: buildContextMock,
+}));
+vi.mock("@/lib/telegram/sendSalesNotification", () => ({ sendSalesNotification: sendMock }));
+
+const { processSubscriptionDeleted } = await import("@/lib/stripe/processSubscriptionDeleted");
+
+describe("processSubscriptionDeleted", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    buildContextMock.mockResolvedValue({
+      email: "fan@example.com",
+      customerLine: "Customer: fan@example.com (cus_9)",
+      planLine: "Plan: $99.00/month",
+      lifetimeLine: "Lifetime value: $0.00",
+    });
+  });
+
+  it("notifies final churn with cancellation feedback", async () => {
+    await processSubscriptionDeleted({
+      id: "sub_1",
+      customer: "cus_9",
+      cancellation_details: { feedback: "too_expensive", reason: "cancellation_requested" },
+    } as unknown as Stripe.Subscription);
+
+    expect(sendMock).toHaveBeenCalledTimes(1);
+    const { email, text } = sendMock.mock.calls[0][0];
+    expect(email).toBe("fan@example.com");
+    expect(text).toContain("Subscription canceled");
+    expect(text).toContain("Feedback: too_expensive");
+    expect(text).toContain("Lifetime value: $0.00");
+  });
+
+  it("omits the feedback line when Stripe has none", async () => {
+    await processSubscriptionDeleted({
+      id: "sub_1",
+      customer: "cus_9",
+      cancellation_details: { feedback: null, reason: null },
+    } as unknown as Stripe.Subscription);
+
+    expect(sendMock.mock.calls[0][0].text).not.toContain("Feedback:");
+  });
+});
diff --git a/lib/stripe/__tests__/processSubscriptionTrialWillEnd.test.ts b/lib/stripe/__tests__/processSubscriptionTrialWillEnd.test.ts
new file mode 100644
index 000000000..511349b59
--- /dev/null
+++ b/lib/stripe/__tests__/processSubscriptionTrialWillEnd.test.ts
@@ -0,0 +1,43 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import type Stripe from "stripe";
+
+const { buildContextMock, sendMock } = vi.hoisted(() => ({
+  buildContextMock: vi.fn(),
+  sendMock: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/buildSubscriptionSalesContext", () => ({
+  buildSubscriptionSalesContext: buildContextMock,
+}));
+vi.mock("@/lib/telegram/sendSalesNotification", () => ({ sendSalesNotification: sendMock }));
+
+const { processSubscriptionTrialWillEnd } = await import(
+  "@/lib/stripe/processSubscriptionTrialWillEnd"
+);
+
+describe("processSubscriptionTrialWillEnd", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    buildContextMock.mockResolvedValue({
+      email: "fan@example.com",
+      customerLine: "Customer: fan@example.com (cus_9)",
+      planLine: "Plan: $99.00/month",
+      lifetimeLine: "Lifetime value: $0.00",
+    });
+  });
+
+  it("notifies that the trial is ending with the conversion date", async () => {
+    await processSubscriptionTrialWillEnd({
+      id: "sub_1",
+      trial_end: 1783415103,
+    } as unknown as Stripe.Subscription);
+
+    expect(sendMock).toHaveBeenCalledTimes(1);
+    const { email, text } = sendMock.mock.calls[0][0];
+    expect(email).toBe("fan@example.com");
+    expect(text).toContain("Trial ending soon");
+    expect(text).toContain("reach out now");
+    expect(text).toContain("Trial ends: 2026-07-07");
+    expect(text).toContain("Lifetime value: $0.00");
+  });
+});
diff --git a/lib/stripe/__tests__/processSubscriptionUpdated.test.ts b/lib/stripe/__tests__/processSubscriptionUpdated.test.ts
new file mode 100644
index 000000000..acfe0dc90
--- /dev/null
+++ b/lib/stripe/__tests__/processSubscriptionUpdated.test.ts
@@ -0,0 +1,75 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import type Stripe from "stripe";
+
+const { buildContextMock, sendMock } = vi.hoisted(() => ({
+  buildContextMock: vi.fn(),
+  sendMock: vi.fn(),
+}));
+
+vi.mock("@/lib/stripe/buildSubscriptionSalesContext", () => ({
+  buildSubscriptionSalesContext: buildContextMock,
+}));
+vi.mock("@/lib/telegram/sendSalesNotification", () => ({ sendSalesNotification: sendMock }));
+
+const { processSubscriptionUpdated } = await import("@/lib/stripe/processSubscriptionUpdated");
+
+const sub = (overrides: object = {}): Stripe.Subscription =>
+  ({
+    id: "sub_1",
+    customer: "cus_9",
+    cancel_at_period_end: false,
+    ...overrides,
+  }) as unknown as Stripe.Subscription;
+
+const prev = (attrs: object): Partial<Stripe.Subscription> => attrs as Partial<Stripe.Subscription>;
+
+describe("processSubscriptionUpdated", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    buildContextMock.mockResolvedValue({
+      email: "fan@example.com",
+      customerLine: "Customer: fan@example.com (cus_9)",
+      planLine: "Plan: $99.00/month",
+      lifetimeLine: "Lifetime value: $0.00",
+    });
+  });
+
+  it("notifies churn scheduled on the false→true cancel_at_period_end flip", async () => {
+    await processSubscriptionUpdated(
+      sub({
+        cancel_at_period_end: true,
+        cancel_at: 1783415103,
+        cancellation_details: { feedback: "too_expensive", reason: "cancellation_requested" },
+      }),
+      prev({ cancel_at_period_end: false }),
+    );
+
+    expect(sendMock).toHaveBeenCalledTimes(1);
+    const { text } = sendMock.mock.calls[0][0];
+    expect(text).toContain("Churn scheduled");
+    expect(text).toContain("Cancels: 2026-07-07");
+    expect(text).toContain("Feedback: too_expensive");
+    expect(text).toContain("Lifetime value: $0.00");
+  });
+
+  it("notifies customer saved on the true→false flip", async () => {
+    await processSubscriptionUpdated(
+      sub({ cancel_at_period_end: false }),
+      prev({ cancel_at_period_end: true }),
+    );
+
+    expect(sendMock).toHaveBeenCalledTimes(1);
+    expect(sendMock.mock.calls[0][0].text).toContain("Cancellation withdrawn");
+  });
+
+  it("stays silent on updates that do not flip cancel_at_period_end (e.g. metadata)", async () => {
+    await processSubscriptionUpdated(sub(), prev({ metadata: { foo: "bar" } }));
+    expect(sendMock).not.toHaveBeenCalled();
+    expect(buildContextMock).not.toHaveBeenCalled();
+  });
+
+  it("stays silent when previous_attributes is undefined", async () => {
+    await processSubscriptionUpdated(sub({ cancel_at_period_end: true }), undefined);
+    expect(sendMock).not.toHaveBeenCalled();
+  });
+});
diff --git a/lib/stripe/__tests__/stripeWebhookHandler.test.ts b/lib/stripe/__tests__/stripeWebhookHandler.test.ts
index c9e3847ae..63ebe389d 100644
--- a/lib/stripe/__tests__/stripeWebhookHandler.test.ts
+++ b/lib/stripe/__tests__/stripeWebhookHandler.test.ts
@@ -6,10 +6,18 @@ const {
   verifyStripeWebhookEventMock,
   processCreditsTopupSessionMock,
   processCreditsTopupPaymentIntentMock,
+  processSubscriptionCreatedMock,
+  processSubscriptionTrialWillEndMock,
+  processSubscriptionUpdatedMock,
+  processSubscriptionDeletedMock,
 } = vi.hoisted(() => ({
   verifyStripeWebhookEventMock: vi.fn(),
   processCreditsTopupSessionMock: vi.fn(),
   processCreditsTopupPaymentIntentMock: vi.fn(),
+  processSubscriptionCreatedMock: vi.fn(),
+  processSubscriptionTrialWillEndMock: vi.fn(),
+  processSubscriptionUpdatedMock: vi.fn(),
+  processSubscriptionDeletedMock: vi.fn(),
 }));
 
 vi.mock("@/lib/stripe/verifyStripeWebhookEvent", () => ({
@@ -21,6 +29,18 @@ vi.mock("@/lib/stripe/processCreditsTopupSession", () => ({
 vi.mock("@/lib/stripe/processCreditsTopupPaymentIntent", () => ({
   processCreditsTopupPaymentIntent: processCreditsTopupPaymentIntentMock,
 }));
+vi.mock("@/lib/stripe/processSubscriptionCreated", () => ({
+  processSubscriptionCreated: processSubscriptionCreatedMock,
+}));
+vi.mock("@/lib/stripe/processSubscriptionTrialWillEnd", () => ({
+  processSubscriptionTrialWillEnd: processSubscriptionTrialWillEndMock,
+}));
+vi.mock("@/lib/stripe/processSubscriptionUpdated", () => ({
+  processSubscriptionUpdated: processSubscriptionUpdatedMock,
+}));
+vi.mock("@/lib/stripe/processSubscriptionDeleted", () => ({
+  processSubscriptionDeleted: processSubscriptionDeletedMock,
+}));
 vi.mock("@/lib/networking/getCorsHeaders", () => ({
   getCorsHeaders: vi.fn(() => ({ "Access-Control-Allow-Origin": "*" })),
 }));
@@ -79,6 +99,51 @@ describe("stripeWebhookHandler", () => {
     expect(processCreditsTopupPaymentIntentMock).not.toHaveBeenCalled();
   });
 
+  it("delegates customer.subscription.created to processSubscriptionCreated", async () => {
+    const sub = { id: "sub_1", status: "trialing" };
+    verifyStripeWebhookEventMock.mockResolvedValue({
+      event: event("customer.subscription.created", sub),
+    });
+    const res = await stripeWebhookHandler(makeReq());
+    expect(res.status).toBe(200);
+    expect(processSubscriptionCreatedMock).toHaveBeenCalledWith(sub);
+  });
+
+  it("delegates customer.subscription.trial_will_end to processSubscriptionTrialWillEnd", async () => {
+    const sub = { id: "sub_1", trial_end: 1783415103 };
+    verifyStripeWebhookEventMock.mockResolvedValue({
+      event: event("customer.subscription.trial_will_end", sub),
+    });
+    const res = await stripeWebhookHandler(makeReq());
+    expect(res.status).toBe(200);
+    expect(processSubscriptionTrialWillEndMock).toHaveBeenCalledWith(sub);
+  });
+
+  it("delegates customer.subscription.updated with previous_attributes", async () => {
+    const sub = { id: "sub_1", cancel_at_period_end: true };
+    const previous = { cancel_at_period_end: false };
+    verifyStripeWebhookEventMock.mockResolvedValue({
+      event: {
+        id: "evt_1",
+        type: "customer.subscription.updated",
+        data: { object: sub, previous_attributes: previous },
+      } as unknown as Stripe.Event,
+    });
+    const res = await stripeWebhookHandler(makeReq());
+    expect(res.status).toBe(200);
+    expect(processSubscriptionUpdatedMock).toHaveBeenCalledWith(sub, previous);
+  });
+
+  it("delegates customer.subscription.deleted to processSubscriptionDeleted", async () => {
+    const sub = { id: "sub_1", status: "canceled" };
+    verifyStripeWebhookEventMock.mockResolvedValue({
+      event: event("customer.subscription.deleted", sub),
+    });
+    const res = await stripeWebhookHandler(makeReq());
+    expect(res.status).toBe(200);
+    expect(processSubscriptionDeletedMock).toHaveBeenCalledWith(sub);
+  });
+
   it("returns 500 when the event handler throws (so Stripe retries)", async () => {
     verifyStripeWebhookEventMock.mockResolvedValue({
       event: event("checkout.session.completed", { id: "cs_x" }),
diff --git a/lib/stripe/buildSubscriptionSalesContext.ts b/lib/stripe/buildSubscriptionSalesContext.ts
new file mode 100644
index 000000000..14d18eb05
--- /dev/null
+++ b/lib/stripe/buildSubscriptionSalesContext.ts
@@ -0,0 +1,41 @@
+import type Stripe from "stripe";
+import { getCustomerEmail } from "@/lib/stripe/getCustomerEmail";
+import { getCustomerLifetimeValue } from "@/lib/stripe/getCustomerLifetimeValue";
+import { formatUsd } from "@/lib/stripe/formatUsd";
+
+export interface SubscriptionSalesContext {
+  email: string | null;
+  customerLine: string;
+  planLine: string;
+  lifetimeLine: string;
+}
+
+/**
+ * Resolves the shared message lines every subscription sales notification
+ * carries: who the customer is, what plan the subscription is on, and the
+ * customer's lifetime value.
+ */
+export const buildSubscriptionSalesContext = async (
+  subscription: Stripe.Subscription,
+): Promise<SubscriptionSalesContext> => {
+  const customerId =
+    typeof subscription.customer === "string" ? subscription.customer : subscription.customer.id;
+
+  const [email, lifetimeCents] = await Promise.all([
+    getCustomerEmail(customerId),
+    getCustomerLifetimeValue(customerId),
+  ]);
+
+  const price = subscription.items?.data?.[0]?.price;
+  const planLine =
+    price?.unit_amount != null && price.recurring?.interval
+      ? `Plan: ${formatUsd(price.unit_amount)}/${price.recurring.interval}`
+      : "Plan: unknown";
+
+  return {
+    email,
+    customerLine: email ? `Customer: ${email} (${customerId})` : `Customer: ${customerId}`,
+    planLine,
+    lifetimeLine: `Lifetime value: ${formatUsd(lifetimeCents)}`,
+  };
+};
diff --git a/lib/stripe/formatStripeTimestamp.ts b/lib/stripe/formatStripeTimestamp.ts
new file mode 100644
index 000000000..b8545a6e8
--- /dev/null
+++ b/lib/stripe/formatStripeTimestamp.ts
@@ -0,0 +1,5 @@
+/**
+ * Formats a Stripe unix-seconds timestamp as an ISO date, e.g. "2026-07-07".
+ */
+export const formatStripeTimestamp = (unixSeconds: number): string =>
+  new Date(unixSeconds * 1000).toISOString().slice(0, 10);
diff --git a/lib/stripe/formatUsd.ts b/lib/stripe/formatUsd.ts
new file mode 100644
index 000000000..90067963c
--- /dev/null
+++ b/lib/stripe/formatUsd.ts
@@ -0,0 +1,7 @@
+/**
+ * Formats a Stripe cents amount as a dollar string, e.g. 9900 → "$99.00".
+ */
+export const formatUsd = (cents: number): string => {
+  const sign = cents < 0 ? "-" : "";
+  return `${sign}$${(Math.abs(cents) / 100).toFixed(2)}`;
+};
diff --git a/lib/stripe/getCustomerEmail.ts b/lib/stripe/getCustomerEmail.ts
new file mode 100644
index 000000000..33e6bd865
--- /dev/null
+++ b/lib/stripe/getCustomerEmail.ts
@@ -0,0 +1,22 @@
+import type Stripe from "stripe";
+import stripeClient from "@/lib/stripe/client";
+
+/**
+ * Resolves a Stripe customer id to its email. Subscription webhook events
+ * only carry the `cus_` id, so notification builders use this lookup.
+ * Returns null (never throws) for deleted customers, missing emails, or
+ * lookup failures — a notification must not fail the webhook for want of
+ * an email.
+ */
+export const getCustomerEmail = async (customerId: string): Promise<string | null> => {
+  try {
+    const customer = (await stripeClient.customers.retrieve(customerId)) as
+      | Stripe.Customer
+      | Stripe.DeletedCustomer;
+    if (customer.deleted) return null;
+    return (customer as Stripe.Customer).email ?? null;
+  } catch (error) {
+    console.error("[getCustomerEmail]", { customerId, error });
+    return null;
+  }
+};
diff --git a/lib/stripe/getCustomerLifetimeValue.ts b/lib/stripe/getCustomerLifetimeValue.ts
new file mode 100644
index 000000000..3fa8d0c30
--- /dev/null
+++ b/lib/stripe/getCustomerLifetimeValue.ts
@@ -0,0 +1,34 @@
+import Stripe from "stripe";
+import stripeClient from "@/lib/stripe/client";
+
+const PAGE_LIMIT = 100;
+
+/**
+ * Lifetime value of a Stripe customer in cents: the sum of all succeeded
+ * charges net of refunds. Charges cover both subscription payments and
+ * credits top-ups in one number — invoices alone would miss top-ups.
+ */
+export const getCustomerLifetimeValue = async (customerId: string): Promise<number> => {
+  let totalCents = 0;
+  let startingAfter: string | undefined;
+  let hasMore = true;
+
+  while (hasMore) {
+    const listParams: Stripe.ChargeListParams = { customer: customerId, limit: PAGE_LIMIT };
+    if (startingAfter) listParams.starting_after = startingAfter;
+
+    const page = await stripeClient.charges.list(listParams);
+
+    for (const charge of page.data) {
+      if (charge.status !== "succeeded") continue;
+      totalCents += charge.amount - charge.amount_refunded;
+    }
+
+    hasMore = page.has_more;
+    const lastId = page.data.at(-1)?.id;
+    if (!lastId) break;
+    startingAfter = lastId;
+  }
+
+  return totalCents;
+};
diff --git a/lib/stripe/processSubscriptionCreated.ts b/lib/stripe/processSubscriptionCreated.ts
new file mode 100644
index 000000000..d32108e6e
--- /dev/null
+++ b/lib/stripe/processSubscriptionCreated.ts
@@ -0,0 +1,26 @@
+import type Stripe from "stripe";
+import { buildSubscriptionSalesContext } from "@/lib/stripe/buildSubscriptionSalesContext";
+import { formatStripeTimestamp } from "@/lib/stripe/formatStripeTimestamp";
+import { sendSalesNotification } from "@/lib/telegram/sendSalesNotification";
+
+/**
+ * Webhook processor for `customer.subscription.created`: announces every
+ * new subscription in the admin Telegram chat — including trials, which
+ * are the "new card on file" moment sales outreach cares about.
+ */
+export async function processSubscriptionCreated(subscription: Stripe.Subscription): Promise<void> {
+  const ctx = await buildSubscriptionSalesContext(subscription);
+  const trialing = subscription.status === "trialing";
+
+  const lines = [
+    trialing ? "🆕 New subscription (trial) — new card on file" : "🆕 New subscription",
+    ctx.customerLine,
+    ctx.planLine,
+  ];
+  if (trialing && subscription.trial_end) {
+    lines.push(`Trial ends: ${formatStripeTimestamp(subscription.trial_end)}`);
+  }
+  lines.push(ctx.lifetimeLine);
+
+  await sendSalesNotification({ email: ctx.email, text: lines.join("\n") });
+}
diff --git a/lib/stripe/processSubscriptionDeleted.ts b/lib/stripe/processSubscriptionDeleted.ts
new file mode 100644
index 000000000..dd46797df
--- /dev/null
+++ b/lib/stripe/processSubscriptionDeleted.ts
@@ -0,0 +1,20 @@
+import type Stripe from "stripe";
+import { buildSubscriptionSalesContext } from "@/lib/stripe/buildSubscriptionSalesContext";
+import { sendSalesNotification } from "@/lib/telegram/sendSalesNotification";
+
+/**
+ * Webhook processor for `customer.subscription.deleted`: the churn is
+ * final — the subscription has actually ended (period end after a
+ * scheduled cancellation, or an immediate cancel).
+ */
+export async function processSubscriptionDeleted(subscription: Stripe.Subscription): Promise<void> {
+  const ctx = await buildSubscriptionSalesContext(subscription);
+
+  const lines = ["❌ Subscription canceled — churn final", ctx.customerLine, ctx.planLine];
+  const { feedback, reason } = subscription.cancellation_details ?? {};
+  if (feedback) lines.push(`Feedback: ${feedback}`);
+  if (reason) lines.push(`Reason: ${reason}`);
+  lines.push(ctx.lifetimeLine);
+
+  await sendSalesNotification({ email: ctx.email, text: lines.join("\n") });
+}
diff --git a/lib/stripe/processSubscriptionTrialWillEnd.ts b/lib/stripe/processSubscriptionTrialWillEnd.ts
new file mode 100644
index 000000000..8da237927
--- /dev/null
+++ b/lib/stripe/processSubscriptionTrialWillEnd.ts
@@ -0,0 +1,23 @@
+import type Stripe from "stripe";
+import { buildSubscriptionSalesContext } from "@/lib/stripe/buildSubscriptionSalesContext";
+import { formatStripeTimestamp } from "@/lib/stripe/formatStripeTimestamp";
+import { sendSalesNotification } from "@/lib/telegram/sendSalesNotification";
+
+/**
+ * Webhook processor for `customer.subscription.trial_will_end` (Stripe
+ * fires it 3 days before the trial converts): the proactive-outreach
+ * window before the customer decides whether to keep paying.
+ */
+export async function processSubscriptionTrialWillEnd(
+  subscription: Stripe.Subscription,
+): Promise<void> {
+  const ctx = await buildSubscriptionSalesContext(subscription);
+
+  const lines = ["⏳ Trial ending soon — reach out now", ctx.customerLine, ctx.planLine];
+  if (subscription.trial_end) {
+    lines.push(`Trial ends: ${formatStripeTimestamp(subscription.trial_end)}`);
+  }
+  lines.push(ctx.lifetimeLine);
+
+  await sendSalesNotification({ email: ctx.email, text: lines.join("\n") });
+}
diff --git a/lib/stripe/processSubscriptionUpdated.ts b/lib/stripe/processSubscriptionUpdated.ts
new file mode 100644
index 000000000..b43af31de
--- /dev/null
+++ b/lib/stripe/processSubscriptionUpdated.ts
@@ -0,0 +1,37 @@
+import type Stripe from "stripe";
+import { buildSubscriptionSalesContext } from "@/lib/stripe/buildSubscriptionSalesContext";
+import { formatStripeTimestamp } from "@/lib/stripe/formatStripeTimestamp";
+import { sendSalesNotification } from "@/lib/telegram/sendSalesNotification";
+
+/**
+ * Webhook processor for `customer.subscription.updated`. Only the
+ * `cancel_at_period_end` flip is a sales signal: false→true is churn
+ * scheduled (the human decision moment, days before the subscription
+ * actually ends — the window where outreach can still save the customer),
+ * true→false is a saved customer. Every other update (metadata, renewal,
+ * plan tweaks) stays silent.
+ */
+export async function processSubscriptionUpdated(
+  subscription: Stripe.Subscription,
+  previousAttributes: Partial<Stripe.Subscription> | undefined,
+): Promise<void> {
+  const previous = previousAttributes?.cancel_at_period_end;
+  const current = subscription.cancel_at_period_end;
+  if (typeof previous !== "boolean" || previous === current) return;
+
+  const ctx = await buildSubscriptionSalesContext(subscription);
+
+  const lines = current
+    ? ["⚠️ Churn scheduled — cancels at period end", ctx.customerLine, ctx.planLine]
+    : ["💚 Cancellation withdrawn — customer saved", ctx.customerLine, ctx.planLine];
+
+  if (current && subscription.cancel_at) {
+    lines.push(`Cancels: ${formatStripeTimestamp(subscription.cancel_at)}`);
+  }
+  const { feedback, reason } = subscription.cancellation_details ?? {};
+  if (current && feedback) lines.push(`Feedback: ${feedback}`);
+  if (current && reason) lines.push(`Reason: ${reason}`);
+  lines.push(ctx.lifetimeLine);
+
+  await sendSalesNotification({ email: ctx.email, text: lines.join("\n") });
+}
diff --git a/lib/stripe/stripeWebhookHandler.ts b/lib/stripe/stripeWebhookHandler.ts
index 39270685c..acbd7e8a2 100644
--- a/lib/stripe/stripeWebhookHandler.ts
+++ b/lib/stripe/stripeWebhookHandler.ts
@@ -3,6 +3,10 @@ import type Stripe from "stripe";
 import { getCorsHeaders } from "@/lib/networking/getCorsHeaders";
 import { processCreditsTopupPaymentIntent } from "@/lib/stripe/processCreditsTopupPaymentIntent";
 import { processCreditsTopupSession } from "@/lib/stripe/processCreditsTopupSession";
+import { processSubscriptionCreated } from "@/lib/stripe/processSubscriptionCreated";
+import { processSubscriptionDeleted } from "@/lib/stripe/processSubscriptionDeleted";
+import { processSubscriptionTrialWillEnd } from "@/lib/stripe/processSubscriptionTrialWillEnd";
+import { processSubscriptionUpdated } from "@/lib/stripe/processSubscriptionUpdated";
 import { verifyStripeWebhookEvent } from "@/lib/stripe/verifyStripeWebhookEvent";
 
 export async function stripeWebhookHandler(request: NextRequest): Promise<NextResponse> {
@@ -18,6 +22,17 @@ export async function stripeWebhookHandler(request: NextRequest): Promise<NextRe
       await processCreditsTopupSession(event.data.object as Stripe.Checkout.Session);
     } else if (event.type === "payment_intent.succeeded") {
       await processCreditsTopupPaymentIntent(event.data.object as Stripe.PaymentIntent);
+    } else if (event.type === "customer.subscription.created") {
+      await processSubscriptionCreated(event.data.object as Stripe.Subscription);
+    } else if (event.type === "customer.subscription.trial_will_end") {
+      await processSubscriptionTrialWillEnd(event.data.object as Stripe.Subscription);
+    } else if (event.type === "customer.subscription.updated") {
+      await processSubscriptionUpdated(
+        event.data.object as Stripe.Subscription,
+        event.data.previous_attributes as Partial<Stripe.Subscription> | undefined,
+      );
+    } else if (event.type === "customer.subscription.deleted") {
+      await processSubscriptionDeleted(event.data.object as Stripe.Subscription);
     }
 
     return NextResponse.json({ received: true }, { status: 200, headers: getCorsHeaders() });
diff --git a/lib/telegram/__tests__/sendSalesNotification.test.ts b/lib/telegram/__tests__/sendSalesNotification.test.ts
new file mode 100644
index 000000000..23660ec67
--- /dev/null
+++ b/lib/telegram/__tests__/sendSalesNotification.test.ts
@@ -0,0 +1,45 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+
+const { sendMessageMock, isTestEmailMock } = vi.hoisted(() => ({
+  sendMessageMock: vi.fn(),
+  isTestEmailMock: vi.fn(),
+}));
+
+vi.mock("@/lib/telegram/sendMessage", () => ({ sendMessage: sendMessageMock }));
+vi.mock("@/lib/emails/isTestEmail", () => ({ isTestEmail: isTestEmailMock }));
+
+const { sendSalesNotification } = await import("@/lib/telegram/sendSalesNotification");
+
+describe("sendSalesNotification", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    isTestEmailMock.mockReturnValue(false);
+    vi.spyOn(console, "error").mockImplementation(() => undefined);
+  });
+  afterEach(() => vi.mocked(console.error).mockRestore());
+
+  it("sends the text via the Telegram sendMessage primitive", async () => {
+    await sendSalesNotification({ email: "fan@example.com", text: "💸 hello" });
+    expect(sendMessageMock).toHaveBeenCalledWith("💸 hello");
+  });
+
+  it("skips test emails", async () => {
+    isTestEmailMock.mockReturnValue(true);
+    await sendSalesNotification({ email: "sweetmantech@gmail.com", text: "x" });
+    expect(sendMessageMock).not.toHaveBeenCalled();
+  });
+
+  it("still sends when the email is unknown (null)", async () => {
+    await sendSalesNotification({ email: null, text: "x" });
+    expect(sendMessageMock).toHaveBeenCalledWith("x");
+    expect(isTestEmailMock).not.toHaveBeenCalled();
+  });
+
+  it("never throws when Telegram fails — logs instead", async () => {
+    sendMessageMock.mockRejectedValue(new Error("telegram down"));
+    await expect(
+      sendSalesNotification({ email: "fan@example.com", text: "x" }),
+    ).resolves.toBeUndefined();
+    expect(console.error).toHaveBeenCalled();
+  });
+});
diff --git a/lib/telegram/sendSalesNotification.ts b/lib/telegram/sendSalesNotification.ts
new file mode 100644
index 000000000..36a0cf820
--- /dev/null
+++ b/lib/telegram/sendSalesNotification.ts
@@ -0,0 +1,28 @@
+import { sendMessage } from "./sendMessage";
+import { isTestEmail } from "@/lib/emails/isTestEmail";
+
+interface SalesNotificationParams {
+  /** Customer email when known — used to filter internal/test accounts. */
+  email: string | null;
+  /** Fully formatted message body. */
+  text: string;
+}
+
+/**
+ * Sends a sales-event message (new subscription, churn, payment) to the
+ * admin Telegram chat. Skips internal/test accounts and never throws —
+ * a Telegram failure must not turn a Stripe webhook delivery into a
+ * non-200 (Stripe would retry and duplicate work).
+ */
+export const sendSalesNotification = async ({
+  email,
+  text,
+}: SalesNotificationParams): Promise<void> => {
+  if (email && isTestEmail(email)) return;
+
+  try {
+    await sendMessage(text);
+  } catch (error) {
+    console.error("Error sending sales notification:", error);
+  }
+};