diff --git a/packages/types/src/telemetry.ts b/packages/types/src/telemetry.ts
index bba1485722..81c20176ff 100644
--- a/packages/types/src/telemetry.ts
+++ b/packages/types/src/telemetry.ts
@@ -61,6 +61,9 @@ export enum TelemetryEventName {
 	ACCOUNT_LOGOUT_CLICKED = "Account Logout Clicked",
 	ACCOUNT_LOGOUT_SUCCESS = "Account Logout Success",
 
+	UPSELL_DISMISSED = "Upsell Dismissed",
+	UPSELL_CLICKED = "Upsell Clicked",
+
 	SCHEMA_VALIDATION_ERROR = "Schema Validation Error",
 	DIFF_APPLICATION_ERROR = "Diff Application Error",
 	SHELL_INTEGRATION_ERROR = "Shell Integration Error",
@@ -181,6 +184,8 @@ export const rooCodeTelemetryEventSchema = z.discriminatedUnion("type", [
 			TelemetryEventName.ACCOUNT_CONNECT_SUCCESS,
 			TelemetryEventName.ACCOUNT_LOGOUT_CLICKED,
 			TelemetryEventName.ACCOUNT_LOGOUT_SUCCESS,
+			TelemetryEventName.UPSELL_DISMISSED,
+			TelemetryEventName.UPSELL_CLICKED,
 			TelemetryEventName.SCHEMA_VALIDATION_ERROR,
 			TelemetryEventName.DIFF_APPLICATION_ERROR,
 			TelemetryEventName.SHELL_INTEGRATION_ERROR,
diff --git a/webview-ui/src/components/common/DismissibleUpsell.tsx b/webview-ui/src/components/common/DismissibleUpsell.tsx
index 2eefb89972..6f0e1ad2dc 100644
--- a/webview-ui/src/components/common/DismissibleUpsell.tsx
+++ b/webview-ui/src/components/common/DismissibleUpsell.tsx
@@ -1,6 +1,8 @@
 import { memo, ReactNode, useEffect, useState, useRef } from "react"
 import { vscode } from "@src/utils/vscode"
 import { useAppTranslation } from "@src/i18n/TranslationContext"
+import { telemetryClient } from "@src/utils/TelemetryClient"
+import { TelemetryEventName } from "@roo-code/types"
 
 interface DismissibleUpsellProps {
 	/** Required unique identifier for this upsell */
@@ -76,7 +78,12 @@ const DismissibleUpsell = memo(
 			}
 		}, [upsellId])
 
-		const handleDismiss = async () => {
+		const handleDismiss = () => {
+			// Track telemetry for dismissal
+			telemetryClient.capture(TelemetryEventName.UPSELL_DISMISSED, {
+				upsellId: upsellId,
+			})
+
 			// First notify the extension to persist the dismissal
 			// This ensures the message is sent even if the component unmounts quickly
 			vscode.postMessage({
@@ -134,6 +141,13 @@ const DismissibleUpsell = memo(
 			<div
 				className={containerClasses}
 				onClick={() => {
+					// Track telemetry for click
+					if (onClick) {
+						telemetryClient.capture(TelemetryEventName.UPSELL_CLICKED, {
+							upsellId: upsellId,
+						})
+					}
+
 					// Call the onClick handler if provided
 					onClick?.()
 					// Also dismiss if dismissOnClick is true
diff --git a/webview-ui/src/components/common/__tests__/DismissibleUpsell.spec.tsx b/webview-ui/src/components/common/__tests__/DismissibleUpsell.spec.tsx
index 3af66dfdf1..69e4e94a4f 100644
--- a/webview-ui/src/components/common/__tests__/DismissibleUpsell.spec.tsx
+++ b/webview-ui/src/components/common/__tests__/DismissibleUpsell.spec.tsx
@@ -1,6 +1,7 @@
 import { render, screen, fireEvent, waitFor, act } from "@testing-library/react"
 import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
 import DismissibleUpsell from "../DismissibleUpsell"
+import { TelemetryEventName } from "@roo-code/types"
 
 // Mock the vscode API
 const mockPostMessage = vi.fn()
@@ -10,6 +11,14 @@ vi.mock("@src/utils/vscode", () => ({
 	},
 }))
 
+// Mock telemetryClient
+const mockCapture = vi.fn()
+vi.mock("@src/utils/TelemetryClient", () => ({
+	telemetryClient: {
+		capture: (eventName: string, properties?: Record<string, any>) => mockCapture(eventName, properties),
+	},
+}))
+
 // Mock the translation hook
 vi.mock("@src/i18n/TranslationContext", () => ({
 	useAppTranslation: () => ({
@@ -26,6 +35,7 @@ vi.mock("@src/i18n/TranslationContext", () => ({
 describe("DismissibleUpsell", () => {
 	beforeEach(() => {
 		mockPostMessage.mockClear()
+		mockCapture.mockClear()
 		vi.clearAllTimers()
 	})
 
@@ -72,7 +82,7 @@ describe("DismissibleUpsell", () => {
 		})
 	})
 
-	it("hides the upsell when dismiss button is clicked", async () => {
+	it("hides the upsell when dismiss button is clicked and tracks telemetry", async () => {
 		const onDismiss = vi.fn()
 		const { container } = render(
 			<DismissibleUpsell upsellId="test-upsell" onDismiss={onDismiss}>
@@ -92,6 +102,11 @@ describe("DismissibleUpsell", () => {
 		const dismissButton = screen.getByRole("button", { name: /dismiss/i })
 		fireEvent.click(dismissButton)
 
+		// Check that telemetry was tracked
+		expect(mockCapture).toHaveBeenCalledWith(TelemetryEventName.UPSELL_DISMISSED, {
+			upsellId: "test-upsell",
+		})
+
 		// Check that the dismiss message was sent BEFORE hiding
 		expect(mockPostMessage).toHaveBeenCalledWith({
 			type: "dismissUpsell",
@@ -351,7 +366,7 @@ describe("DismissibleUpsell", () => {
 		})
 	})
 
-	it("calls onClick when the container is clicked", async () => {
+	it("calls onClick when the container is clicked and tracks telemetry", async () => {
 		const onClick = vi.fn()
 		render(
 			<DismissibleUpsell upsellId="test-upsell" onClick={onClick}>
@@ -372,6 +387,11 @@ describe("DismissibleUpsell", () => {
 		fireEvent.click(container)
 
 		expect(onClick).toHaveBeenCalledTimes(1)
+
+		// Check that telemetry was tracked
+		expect(mockCapture).toHaveBeenCalledWith(TelemetryEventName.UPSELL_CLICKED, {
+			upsellId: "test-upsell",
+		})
 	})
 
 	it("does not call onClick when dismiss button is clicked", async () => {
@@ -470,7 +490,7 @@ describe("DismissibleUpsell", () => {
 		})
 	})
 
-	it("dismisses when clicked if dismissOnClick is true", async () => {
+	it("dismisses when clicked if dismissOnClick is true and tracks both telemetry events", async () => {
 		const onClick = vi.fn()
 		const onDismiss = vi.fn()
 		const { container } = render(
@@ -493,6 +513,14 @@ describe("DismissibleUpsell", () => {
 		expect(onClick).toHaveBeenCalledTimes(1)
 		expect(onDismiss).toHaveBeenCalledTimes(1)
 
+		// Check that both telemetry events were tracked
+		expect(mockCapture).toHaveBeenCalledWith(TelemetryEventName.UPSELL_CLICKED, {
+			upsellId: "test-upsell",
+		})
+		expect(mockCapture).toHaveBeenCalledWith(TelemetryEventName.UPSELL_DISMISSED, {
+			upsellId: "test-upsell",
+		})
+
 		expect(mockPostMessage).toHaveBeenCalledWith({
 			type: "dismissUpsell",
 			upsellId: "test-upsell",
@@ -503,6 +531,46 @@ describe("DismissibleUpsell", () => {
 		})
 	})
 
+	it("dismisses on container click when dismissOnClick is true and no onClick is provided; tracks only dismissal", async () => {
+		const onDismiss = vi.fn()
+		const { container } = render(
+			<DismissibleUpsell upsellId="test-upsell" onDismiss={onDismiss} dismissOnClick={true}>
+				<div>Test content</div>
+			</DismissibleUpsell>,
+		)
+
+		// Make component visible
+		makeUpsellVisible()
+
+		// Wait for component to be visible
+		await waitFor(() => {
+			expect(screen.getByText("Test content")).toBeInTheDocument()
+		})
+
+		// Click on the container (not the dismiss button)
+		const containerDiv = screen.getByText("Test content").parentElement as HTMLElement
+		fireEvent.click(containerDiv)
+
+		// onDismiss should be called
+		expect(onDismiss).toHaveBeenCalledTimes(1)
+
+		// Telemetry: only dismissal should be tracked
+		expect(mockCapture).toHaveBeenCalledWith(TelemetryEventName.UPSELL_DISMISSED, {
+			upsellId: "test-upsell",
+		})
+		expect(mockCapture).not.toHaveBeenCalledWith(TelemetryEventName.UPSELL_CLICKED, expect.anything())
+
+		// Dismiss message should be sent
+		expect(mockPostMessage).toHaveBeenCalledWith({
+			type: "dismissUpsell",
+			upsellId: "test-upsell",
+		})
+
+		// Component should be hidden
+		await waitFor(() => {
+			expect(container.firstChild).toBeNull()
+		})
+	})
 	it("does not dismiss when clicked if dismissOnClick is false", async () => {
 		const onClick = vi.fn()
 		const onDismiss = vi.fn()