diff --git a/packages/types/src/telemetry.ts b/packages/types/src/telemetry.ts
index cd6be8c5440..7fed0593c0d 100644
--- a/packages/types/src/telemetry.ts
+++ b/packages/types/src/telemetry.ts
@@ -40,6 +40,7 @@ export enum TelemetryEventName {
 	AUTO_PURGE_FAILED = "Auto Purge Failed",
 	MANUAL_PURGE_TRIGGERED = "Manual Purge Triggered",
 	GHOST_SERVICE_DISABLED = "Ghost Service Disabled",
+	ASK_APPROVAL = "Ask Approval",
 	// kilocode_change end
 
 	TASK_CREATED = "Task Created",
diff --git a/src/core/assistant-message/kilocode/captureAskApprovalEvent.ts b/src/core/assistant-message/kilocode/captureAskApprovalEvent.ts
new file mode 100644
index 00000000000..de126a9e211
--- /dev/null
+++ b/src/core/assistant-message/kilocode/captureAskApprovalEvent.ts
@@ -0,0 +1,6 @@
+import { TelemetryEventName, ToolName } from "@roo-code/types"
+import { TelemetryService } from "@roo-code/telemetry"
+
+export function captureAskApproval(tool: ToolName, isApproved: boolean) {
+	TelemetryService.instance.captureEvent(TelemetryEventName.ASK_APPROVAL, { tool, isApproved })
+}
diff --git a/src/core/assistant-message/presentAssistantMessage.ts b/src/core/assistant-message/presentAssistantMessage.ts
index 3279c9c4b94..e1ab2942cc8 100644
--- a/src/core/assistant-message/presentAssistantMessage.ts
+++ b/src/core/assistant-message/presentAssistantMessage.ts
@@ -44,6 +44,7 @@ import { experiments, EXPERIMENT_IDS } from "../../shared/experiments"
 import { applyDiffToolLegacy } from "../tools/applyDiffTool"
 import { yieldPromise } from "../kilocode"
 import Anthropic from "@anthropic-ai/sdk" // kilocode_change
+import { captureAskApproval } from "./kilocode/captureAskApprovalEvent"
 
 /**
  * Processes and presents assistant message content to the user interface.
@@ -334,8 +335,10 @@ export async function presentAssistantMessage(cline: Task) {
 						// Gatekeeper denied the action
 						pushToolResult(formatResponse.toolDenied())
 						cline.didRejectTool = true
+						captureAskApproval(block.name, false)
 						return false
 					}
+					captureAskApproval(block.name, true)
 					return true
 				}
 				// kilocode_change end
@@ -357,6 +360,7 @@ export async function presentAssistantMessage(cline: Task) {
 						pushToolResult(formatResponse.toolDenied())
 					}
 					cline.didRejectTool = true
+					captureAskApproval(block.name, false) // kilocode_change
 					return false
 				}
 
@@ -366,6 +370,7 @@ export async function presentAssistantMessage(cline: Task) {
 					pushToolResult(formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images))
 				}
 
+				captureAskApproval(block.name, true) // kilocode_change
 				return true
 			}
 
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index b874eaa58f3..4d95547879b 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -3128,7 +3128,8 @@ ${prompt}
 
 	public async getTelemetryProperties(): Promise<TelemetryProperties> {
 		// kilocode_change start
-		const { apiConfiguration, experiments } = await this.getState()
+		const state = await this.getState()
+		const { apiConfiguration, experiments } = state
 		const task = this.getCurrentTask()
 
 		async function getModelId() {
@@ -3187,6 +3188,34 @@ ${prompt}
 				}
 			}
 		}
+
+		const getAutoApproveSettings = () => {
+			try {
+				return {
+					autoApprove: {
+						autoApprovalEnabled: !!state.autoApprovalEnabled,
+						alwaysAllowBrowser: !!state.alwaysAllowBrowser,
+						alwaysAllowExecute: !!state.alwaysAllowExecute,
+						alwaysAllowFollowupQuestions: !!state.alwaysAllowFollowupQuestions,
+						alwaysAllowMcp: !!state.alwaysAllowMcp,
+						alwaysAllowModeSwitch: !!state.alwaysAllowModeSwitch,
+						alwaysAllowReadOnly: !!state.alwaysAllowReadOnly,
+						alwaysAllowReadOnlyOutsideWorkspace: !!state.alwaysAllowReadOnlyOutsideWorkspace,
+						alwaysAllowSubtasks: !!state.alwaysAllowSubtasks,
+						alwaysAllowUpdateTodoList: !!state.alwaysAllowUpdateTodoList,
+						alwaysAllowWrite: !!state.alwaysAllowWrite,
+						alwaysAllowWriteOutsideWorkspace: !!state.alwaysAllowWriteOutsideWorkspace,
+						alwaysAllowWriteProtected: !!state.alwaysAllowWriteProtected,
+						alwaysApproveResubmit: !!state.alwaysApproveResubmit,
+						yoloModel: !!state.yoloMode,
+					},
+				}
+			} catch (error) {
+				return {
+					autoApproveException: stringifyError(error),
+				}
+			}
+		}
 		// kilocode_change end
 
 		return {
@@ -3197,6 +3226,7 @@ ${prompt}
 			...getMemory(),
 			...getFastApply(),
 			...getOpenRouter(),
+			...getAutoApproveSettings(),
 			// kilocode_change end
 			...(await this.getTaskProperties()),
 			...(await this.getGitProperties()),