diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts b/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts
index e8e96696e52..2f989dacea2 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts
@@ -11,9 +11,10 @@ import { localize, localize2 } from '../../../../../nls.js';
 import { Action2, MenuId, registerAction2 } from '../../../../../platform/actions/common/actions.js';
 import { Categories } from '../../../../../platform/action/common/actionCommonCategories.js';
 import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
-import { IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
+import { IDialogService, IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
 import { INotificationService, Severity } from '../../../../../platform/notification/common/notification.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { ActiveEditorContext } from '../../../../common/contextkeys.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { isChatViewTitleActionContext } from '../../common/actions/chatActions.js';
@@ -126,6 +127,7 @@ export function registerChatOpenAgentDebugPanelAction() {
 			const fileDialogService = accessor.get(IFileDialogService);
 			const fileService = accessor.get(IFileService);
 			const notificationService = accessor.get(INotificationService);
+			const telemetryService = accessor.get(ITelemetryService);
 
 			const sessionResource = chatDebugService.activeSessionResource;
 			if (!sessionResource) {
@@ -146,6 +148,10 @@ export function registerChatOpenAgentDebugPanelAction() {
 			}
 
 			await fileService.writeFile(outputPath, VSBuffer.wrap(data));
+
+			telemetryService.publicLog2<ChatDebugExportEvent, ChatDebugExportClassification>('chatDebugLogExported', {
+				fileSizeBytes: data.byteLength,
+			});
 		}
 	});
 
@@ -169,10 +175,12 @@ export function registerChatOpenAgentDebugPanelAction() {
 
 		async run(accessor: ServicesAccessor): Promise<void> {
 			const chatDebugService = accessor.get(IChatDebugService);
+			const dialogService = accessor.get(IDialogService);
 			const editorService = accessor.get(IEditorService);
 			const fileDialogService = accessor.get(IFileDialogService);
 			const fileService = accessor.get(IFileService);
 			const notificationService = accessor.get(INotificationService);
+			const telemetryService = accessor.get(ITelemetryService);
 
 			const defaultUri = joinPath(await fileDialogService.defaultFilePath(), defaultDebugLogFileName);
 			const result = await fileDialogService.showOpenDialog({
@@ -187,19 +195,59 @@ export function registerChatOpenAgentDebugPanelAction() {
 			const maxImportSize = 50 * 1024 * 1024; // 50 MB
 			const stat = await fileService.stat(result[0]);
 			if (stat.size !== undefined && stat.size > maxImportSize) {
-				notificationService.notify({ severity: Severity.Warning, message: localize('chatDebugLog.fileTooLarge', "The selected file exceeds the 50 MB size limit for log imports.") });
+				telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+					fileSizeBytes: stat.size,
+					result: 'fileTooLarge',
+				});
+				await dialogService.warn(
+					localize('chatDebugLog.fileTooLargeTitle', "File Too Large"),
+					localize('chatDebugLog.fileTooLargeDetail', "The selected file ({0} MB) exceeds the 50 MB size limit for debug log imports.", (stat.size / (1024 * 1024)).toFixed(1))
+				);
 				return;
 			}
 
 			const content = await fileService.readFile(result[0]);
 			const sessionUri = await chatDebugService.importLog(content.value.buffer);
 			if (!sessionUri) {
+				telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+					fileSizeBytes: content.value.byteLength,
+					result: 'providerFailed',
+				});
 				notificationService.notify({ severity: Severity.Warning, message: localize('chatDebugLog.importFailed', "Import is not supported by the current provider.") });
 				return;
 			}
 
+			telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+				fileSizeBytes: content.value.byteLength,
+				result: 'success',
+			});
+
 			const options: IChatDebugEditorOptions = { pinned: true, sessionResource: sessionUri, viewHint: 'overview' };
 			await editorService.openEditor(ChatDebugEditorInput.instance, options);
 		}
 	});
 }
+
+// Telemetry types
+
+type ChatDebugExportEvent = {
+	fileSizeBytes: number;
+};
+
+type ChatDebugExportClassification = {
+	fileSizeBytes: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Size of the exported chat debug log file in bytes.' };
+	owner: 'vijayu';
+	comment: 'Tracks usage of the debug panel export feature.';
+};
+
+type ChatDebugImportEvent = {
+	fileSizeBytes: number;
+	result: 'success' | 'fileTooLarge' | 'providerFailed';
+};
+
+type ChatDebugImportClassification = {
+	fileSizeBytes: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Size of the imported chat debug log file in bytes.' };
+	result: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Outcome of the chat debug file import: success, fileTooLarge, or providerFailed.' };
+	owner: 'vijayu';
+	comment: 'Tracks usage of the debug panel import feature and failure modes.';
+};