diff --git a/packages/cli/src/InternalHooks.ts b/packages/cli/src/InternalHooks.ts
index b093b93485215..55a39ed88d08a 100644
--- a/packages/cli/src/InternalHooks.ts
+++ b/packages/cli/src/InternalHooks.ts
@@ -262,4 +262,14 @@ export class InternalHooksClass implements IInternalHooksClass {
 	async onUserSignup(userSignupData: { user_id: string }): Promise<void> {
 		return this.telemetry.track('User signed up', userSignupData);
 	}
+
+	async onEmailFailed(failedEmailData: {
+		user_id: string;
+		message_type: 'Reset password' | 'New user invite' | 'Resend invite';
+	}): Promise<void> {
+		return this.telemetry.track(
+			'Instance failed to send transactional email to user',
+			failedEmailData,
+		);
+	}
 }
diff --git a/packages/cli/src/UserManagement/routes/passwordReset.ts b/packages/cli/src/UserManagement/routes/passwordReset.ts
index 7dbb630283d30..4ac00e2cc234e 100644
--- a/packages/cli/src/UserManagement/routes/passwordReset.ts
+++ b/packages/cli/src/UserManagement/routes/passwordReset.ts
@@ -88,6 +88,10 @@ export function passwordResetNamespace(this: N8nApp): void {
 					domain: baseUrl,
 				});
 			} catch (error) {
+				void InternalHooksManager.getInstance().onEmailFailed({
+					user_id: user.id,
+					message_type: 'Reset password',
+				});
 				if (error instanceof Error) {
 					throw new ResponseHelper.ResponseError(
 						`Please contact your administrator: ${error.message}`,
diff --git a/packages/cli/src/UserManagement/routes/users.ts b/packages/cli/src/UserManagement/routes/users.ts
index 8391c90e1491b..85dad09dccaae 100644
--- a/packages/cli/src/UserManagement/routes/users.ts
+++ b/packages/cli/src/UserManagement/routes/users.ts
@@ -194,6 +194,10 @@ export function usersNamespace(this: N8nApp): void {
 							message_type: 'New user invite',
 						});
 					} else {
+						void InternalHooksManager.getInstance().onEmailFailed({
+							user_id: req.user.id,
+							message_type: 'New user invite',
+						});
 						Logger.error('Failed to send email', {
 							userId: req.user.id,
 							inviteAcceptUrl,
@@ -530,6 +534,10 @@ export function usersNamespace(this: N8nApp): void {
 			});
 
 			if (!result?.success) {
+				void InternalHooksManager.getInstance().onEmailFailed({
+					user_id: req.user.id,
+					message_type: 'Resend invite',
+				});
 				Logger.error('Failed to send email', {
 					email: reinvitee.email,
 					inviteAcceptUrl,