diff --git a/src/activate/registerCommands.ts b/src/activate/registerCommands.ts
index ffb419ddfd..b6d2edb00d 100644
--- a/src/activate/registerCommands.ts
+++ b/src/activate/registerCommands.ts
@@ -3,6 +3,7 @@ import delay from "delay"
 
 import { ClineProvider } from "../core/webview/ClineProvider"
 import { ContextProxy } from "../core/config/ContextProxy"
+import { telemetryService } from "../services/telemetry/TelemetryService"
 
 import { registerHumanRelayCallback, unregisterHumanRelayCallback, handleHumanRelayResponse } from "./humanRelay"
 import { handleNewTask } from "./handleTask"
@@ -71,6 +72,8 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 				return
 			}
 
+			telemetryService.captureTitleButtonClicked("plus")
+
 			await visibleProvider.removeClineFromStack()
 			await visibleProvider.postStateToWebview()
 			await visibleProvider.postMessageToWebview({ type: "action", action: "chatButtonClicked" })
@@ -82,6 +85,8 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 				return
 			}
 
+			telemetryService.captureTitleButtonClicked("mcp")
+
 			visibleProvider.postMessageToWebview({ type: "action", action: "mcpButtonClicked" })
 		},
 		"roo-cline.promptsButtonClicked": () => {
@@ -91,9 +96,15 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 				return
 			}
 
+			telemetryService.captureTitleButtonClicked("prompts")
+
 			visibleProvider.postMessageToWebview({ type: "action", action: "promptsButtonClicked" })
 		},
-		"roo-cline.popoutButtonClicked": () => openClineInNewTab({ context, outputChannel }),
+		"roo-cline.popoutButtonClicked": () => {
+			telemetryService.captureTitleButtonClicked("popout")
+
+			return openClineInNewTab({ context, outputChannel })
+		},
 		"roo-cline.openInNewTab": () => openClineInNewTab({ context, outputChannel }),
 		"roo-cline.settingsButtonClicked": () => {
 			const visibleProvider = getVisibleProviderOrLog(outputChannel)
@@ -102,6 +113,8 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 				return
 			}
 
+			telemetryService.captureTitleButtonClicked("settings")
+
 			visibleProvider.postMessageToWebview({ type: "action", action: "settingsButtonClicked" })
 		},
 		"roo-cline.historyButtonClicked": () => {
@@ -111,9 +124,13 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 				return
 			}
 
+			telemetryService.captureTitleButtonClicked("history")
+
 			visibleProvider.postMessageToWebview({ type: "action", action: "historyButtonClicked" })
 		},
 		"roo-cline.helpButtonClicked": () => {
+			telemetryService.captureTitleButtonClicked("help")
+
 			vscode.env.openExternal(vscode.Uri.parse("https://docs.roocode.com"))
 		},
 		"roo-cline.showHumanRelayDialog": (params: { requestId: string; promptText: string }) => {
diff --git a/src/services/telemetry/TelemetryService.ts b/src/services/telemetry/TelemetryService.ts
index 031456f62e..37423542b0 100644
--- a/src/services/telemetry/TelemetryService.ts
+++ b/src/services/telemetry/TelemetryService.ts
@@ -145,6 +145,14 @@ class TelemetryService {
 		this.captureEvent(PostHogClient.EVENTS.ERRORS.CONSECUTIVE_MISTAKE_ERROR, { taskId })
 	}
 
+	/**
+	 * Captures a title button click event
+	 * @param button The button that was clicked
+	 */
+	public captureTitleButtonClicked(button: string): void {
+		this.captureEvent("Title Button Clicked", { button })
+	}
+
 	/**
 	 * Checks if telemetry is currently enabled
 	 * @returns Whether telemetry is enabled