diff --git a/packages/cli/src/Interfaces.ts b/packages/cli/src/Interfaces.ts
index de0313ad016e8..7d151093fac0d 100644
--- a/packages/cli/src/Interfaces.ts
+++ b/packages/cli/src/Interfaces.ts
@@ -333,6 +333,16 @@ export interface IDiagnosticInfo {
 	};
 	deploymentType: string;
 	binaryDataMode: string;
+	n8n_multi_user_allowed: boolean;
+	smtp_set_up: boolean;
+}
+
+export interface ITelemetryUserDeletionData {
+	user_id: string;
+	target_user_old_status: 'active' | 'invited';
+	migration_strategy?: 'transfer_data' | 'delete_data';
+	target_user_id?: string;
+	migration_user_id?: string;
 }
 
 export interface IInternalHooksClass {
@@ -341,15 +351,29 @@ export interface IInternalHooksClass {
 		diagnosticInfo: IDiagnosticInfo,
 		firstWorkflowCreatedAt?: Date,
 	): Promise<unknown[]>;
-	onPersonalizationSurveySubmitted(answers: IPersonalizationSurveyAnswers): Promise<void>;
-	onWorkflowCreated(workflow: IWorkflowBase): Promise<void>;
-	onWorkflowDeleted(workflowId: string): Promise<void>;
-	onWorkflowSaved(workflow: IWorkflowBase): Promise<void>;
+	onPersonalizationSurveySubmitted(userId: string, answers: Record<string, string>): Promise<void>;
+	onWorkflowCreated(userId: string, workflow: IWorkflowBase): Promise<void>;
+	onWorkflowDeleted(userId: string, workflowId: string): Promise<void>;
+	onWorkflowSaved(userId: string, workflow: IWorkflowBase): Promise<void>;
 	onWorkflowPostExecute(
 		executionId: string,
 		workflow: IWorkflowBase,
 		runData?: IRun,
+		userId?: string,
 	): Promise<void>;
+	onUserDeletion(userId: string, userDeletionData: ITelemetryUserDeletionData): Promise<void>;
+	onUserInvite(userInviteData: { user_id: string; target_user_id: string[] }): Promise<void>;
+	onUserReinvite(userReinviteData: { user_id: string; target_user_id: string }): Promise<void>;
+	onUserUpdate(userUpdateData: { user_id: string; fields_changed: string[] }): Promise<void>;
+	onUserInviteEmailClick(userInviteClickData: { user_id: string }): Promise<void>;
+	onUserPasswordResetEmailClick(userPasswordResetData: { user_id: string }): Promise<void>;
+	onUserTransactionalEmail(userTransactionalEmailData: {
+		user_id: string;
+		message_type: 'Reset password' | 'New user invite' | 'Resend invite';
+	}): Promise<void>;
+	onUserPasswordResetRequestClick(userPasswordResetData: { user_id: string }): Promise<void>;
+	onInstanceOwnerSetup(instanceOwnerSetupData: { user_id: string }): Promise<void>;
+	onUserSignup(userSignupData: { user_id: string }): Promise<void>;
 }
 
 export interface IN8nConfig {
diff --git a/packages/cli/src/InternalHooks.ts b/packages/cli/src/InternalHooks.ts
index 068885ef13373..f25dd878b8871 100644
--- a/packages/cli/src/InternalHooks.ts
+++ b/packages/cli/src/InternalHooks.ts
@@ -4,7 +4,7 @@ import { IDataObject, INodeTypes, IRun, TelemetryHelpers } from 'n8n-workflow';
 import {
 	IDiagnosticInfo,
 	IInternalHooksClass,
-	IPersonalizationSurveyAnswers,
+	ITelemetryUserDeletionData,
 	IWorkflowBase,
 	IWorkflowDb,
 } from '.';
@@ -34,6 +34,8 @@ export class InternalHooksClass implements IInternalHooksClass {
 			execution_variables: diagnosticInfo.executionVariables,
 			n8n_deployment_type: diagnosticInfo.deploymentType,
 			n8n_binary_data_mode: diagnosticInfo.binaryDataMode,
+			n8n_multi_user_allowed: diagnosticInfo.n8n_multi_user_allowed,
+			smtp_set_up: diagnosticInfo.smtp_set_up,
 		};
 
 		return Promise.all([
@@ -45,8 +47,12 @@ export class InternalHooksClass implements IInternalHooksClass {
 		]);
 	}
 
-	async onPersonalizationSurveySubmitted(answers: IPersonalizationSurveyAnswers): Promise<void> {
+	async onPersonalizationSurveySubmitted(
+		userId: string,
+		answers: Record<string, string>,
+	): Promise<void> {
 		return this.telemetry.track('User responded to personalization questions', {
+			user_id: userId,
 			company_size: answers.companySize,
 			coding_skill: answers.codingSkill,
 			work_area: answers.workArea,
@@ -56,25 +62,28 @@ export class InternalHooksClass implements IInternalHooksClass {
 		});
 	}
 
-	async onWorkflowCreated(workflow: IWorkflowBase): Promise<void> {
+	async onWorkflowCreated(userId: string, workflow: IWorkflowBase): Promise<void> {
 		const { nodeGraph } = TelemetryHelpers.generateNodesGraph(workflow, this.nodeTypes);
 		return this.telemetry.track('User created workflow', {
+			user_id: userId,
 			workflow_id: workflow.id,
 			node_graph: nodeGraph,
 			node_graph_string: JSON.stringify(nodeGraph),
 		});
 	}
 
-	async onWorkflowDeleted(workflowId: string): Promise<void> {
+	async onWorkflowDeleted(userId: string, workflowId: string): Promise<void> {
 		return this.telemetry.track('User deleted workflow', {
+			user_id: userId,
 			workflow_id: workflowId,
 		});
 	}
 
-	async onWorkflowSaved(workflow: IWorkflowDb): Promise<void> {
+	async onWorkflowSaved(userId: string, workflow: IWorkflowDb): Promise<void> {
 		const { nodeGraph } = TelemetryHelpers.generateNodesGraph(workflow, this.nodeTypes);
 
 		return this.telemetry.track('User saved workflow', {
+			user_id: userId,
 			workflow_id: workflow.id,
 			node_graph: nodeGraph,
 			node_graph_string: JSON.stringify(nodeGraph),
@@ -87,6 +96,7 @@ export class InternalHooksClass implements IInternalHooksClass {
 		executionId: string,
 		workflow: IWorkflowBase,
 		runData?: IRun,
+		userId?: string,
 	): Promise<void> {
 		const promises = [Promise.resolve()];
 		const properties: IDataObject = {
@@ -95,6 +105,10 @@ export class InternalHooksClass implements IInternalHooksClass {
 			version_cli: this.versionCli,
 		};
 
+		if (userId) {
+			properties.user_id = userId;
+		}
+
 		if (runData !== undefined) {
 			properties.execution_mode = runData.mode;
 			properties.success = !!runData.finished;
@@ -188,4 +202,62 @@ export class InternalHooksClass implements IInternalHooksClass {
 
 		return Promise.race([timeoutPromise, this.telemetry.trackN8nStop()]);
 	}
+
+	async onUserDeletion(
+		userId: string,
+		userDeletionData: ITelemetryUserDeletionData,
+	): Promise<void> {
+		return this.telemetry.track('User deleted user', { ...userDeletionData, user_id: userId });
+	}
+
+	async onUserInvite(userInviteData: { user_id: string; target_user_id: string[] }): Promise<void> {
+		return this.telemetry.track('User invited new user', userInviteData);
+	}
+
+	async onUserReinvite(userReinviteData: {
+		user_id: string;
+		target_user_id: string;
+	}): Promise<void> {
+		return this.telemetry.track('User resent new user invite email', userReinviteData);
+	}
+
+	async onUserUpdate(userUpdateData: { user_id: string; fields_changed: string[] }): Promise<void> {
+		return this.telemetry.track('User changed personal settings', userUpdateData);
+	}
+
+	async onUserInviteEmailClick(userInviteClickData: { user_id: string }): Promise<void> {
+		return this.telemetry.track('User clicked invite link from email', userInviteClickData);
+	}
+
+	async onUserPasswordResetEmailClick(userPasswordResetData: { user_id: string }): Promise<void> {
+		return this.telemetry.track(
+			'User clicked password reset link from email',
+			userPasswordResetData,
+		);
+	}
+
+	async onUserTransactionalEmail(userTransactionalEmailData: {
+		user_id: string;
+		message_type: 'Reset password' | 'New user invite' | 'Resend invite';
+	}): Promise<void> {
+		return this.telemetry.track(
+			'Instance sent transactional email to user',
+			userTransactionalEmailData,
+		);
+	}
+
+	async onUserPasswordResetRequestClick(userPasswordResetData: { user_id: string }): Promise<void> {
+		return this.telemetry.track(
+			'User requested password reset while logged out',
+			userPasswordResetData,
+		);
+	}
+
+	async onInstanceOwnerSetup(instanceOwnerSetupData: { user_id: string }): Promise<void> {
+		return this.telemetry.track('Owner finished instance setup', instanceOwnerSetupData);
+	}
+
+	async onUserSignup(userSignupData: { user_id: string }): Promise<void> {
+		return this.telemetry.track('User signed up', userSignupData);
+	}
 }
diff --git a/packages/cli/src/Server.ts b/packages/cli/src/Server.ts
index fbf5777a36a00..eb1a261a0c52e 100644
--- a/packages/cli/src/Server.ts
+++ b/packages/cli/src/Server.ts
@@ -787,7 +787,7 @@ class App {
 				}
 
 				await this.externalHooks.run('workflow.afterCreate', [savedWorkflow]);
-				void InternalHooksManager.getInstance().onWorkflowCreated(newWorkflow);
+				void InternalHooksManager.getInstance().onWorkflowCreated(req.user.id, newWorkflow);
 
 				const { id, ...rest } = savedWorkflow;
 
@@ -1128,7 +1128,7 @@ class App {
 
 				await Db.collections.Workflow!.delete(workflowId);
 
-				void InternalHooksManager.getInstance().onWorkflowDeleted(workflowId);
+				void InternalHooksManager.getInstance().onWorkflowDeleted(req.user.id, workflowId);
 				await this.externalHooks.run('workflow.afterDelete', [workflowId]);
 
 				return true;
@@ -2925,6 +2925,10 @@ export async function start(): Promise<void> {
 			},
 			deploymentType: config.get('deployment.type'),
 			binaryDataMode: binarDataConfig.mode,
+			n8n_multi_user_allowed:
+				config.get('userManagement.disabled') === false ||
+				config.get('userManagement.hasOwner') === true,
+			smtp_set_up: config.get('userManagement.emails.mode') === 'smtp',
 		};
 
 		void Db.collections
diff --git a/packages/cli/src/UserManagement/routes/auth.ts b/packages/cli/src/UserManagement/routes/auth.ts
index b98b40ecaf707..f53c716e47d74 100644
--- a/packages/cli/src/UserManagement/routes/auth.ts
+++ b/packages/cli/src/UserManagement/routes/auth.ts
@@ -1,3 +1,4 @@
+/* eslint-disable @typescript-eslint/naming-convention */
 /* eslint-disable import/no-cycle */
 /* eslint-disable @typescript-eslint/no-non-null-assertion */
 /* eslint-disable @typescript-eslint/no-unsafe-member-access */
@@ -10,6 +11,7 @@ import { issueCookie, resolveJwt } from '../auth/jwt';
 import { N8nApp, PublicUser } from '../Interfaces';
 import { isInstanceOwnerSetup, sanitizeUser } from '../UserManagementHelper';
 import { User } from '../../databases/entities/User';
+import type { LoginRequest } from '../../requests';
 
 export function authenticationMethods(this: N8nApp): void {
 	/**
@@ -19,7 +21,7 @@ export function authenticationMethods(this: N8nApp): void {
 	 */
 	this.app.post(
 		`/${this.restEndpoint}/login`,
-		ResponseHelper.send(async (req: Request, res: Response): Promise<PublicUser> => {
+		ResponseHelper.send(async (req: LoginRequest, res: Response): Promise<PublicUser> => {
 			if (!req.body.email) {
 				throw new Error('Email is required to log in');
 			}
@@ -32,7 +34,7 @@ export function authenticationMethods(this: N8nApp): void {
 			try {
 				user = await Db.collections.User!.findOne(
 					{
-						email: req.body.email as string,
+						email: req.body.email,
 					},
 					{
 						relations: ['globalRole'],
@@ -107,7 +109,7 @@ export function authenticationMethods(this: N8nApp): void {
 	 */
 	this.app.post(
 		`/${this.restEndpoint}/logout`,
-		ResponseHelper.send(async (req: Request, res: Response): Promise<IDataObject> => {
+		ResponseHelper.send(async (_, res: Response): Promise<IDataObject> => {
 			res.clearCookie(AUTH_COOKIE_NAME);
 			return {
 				loggedOut: true,
diff --git a/packages/cli/src/UserManagement/routes/me.ts b/packages/cli/src/UserManagement/routes/me.ts
index e804b09bb6717..1c4ed9f427afe 100644
--- a/packages/cli/src/UserManagement/routes/me.ts
+++ b/packages/cli/src/UserManagement/routes/me.ts
@@ -6,7 +6,7 @@ import express = require('express');
 import validator from 'validator';
 import { LoggerProxy as Logger } from 'n8n-workflow';
 
-import { Db, ResponseHelper } from '../..';
+import { Db, InternalHooksManager, ResponseHelper } from '../..';
 import { issueCookie } from '../auth/jwt';
 import { N8nApp, PublicUser } from '../Interfaces';
 import { validatePassword, sanitizeUser } from '../UserManagementHelper';
@@ -60,6 +60,12 @@ export function meNamespace(this: N8nApp): void {
 
 				await issueCookie(res, user);
 
+				const updatedkeys = Object.keys(req.body);
+				void InternalHooksManager.getInstance().onUserUpdate({
+					user_id: req.user.id,
+					fields_changed: updatedkeys,
+				});
+
 				return sanitizeUser(user);
 			},
 		),
@@ -99,6 +105,11 @@ export function meNamespace(this: N8nApp): void {
 
 			await issueCookie(res, user);
 
+			void InternalHooksManager.getInstance().onUserUpdate({
+				user_id: req.user.id,
+				fields_changed: ['password'],
+			});
+
 			return { success: true };
 		}),
 	);
@@ -132,6 +143,11 @@ export function meNamespace(this: N8nApp): void {
 
 			Logger.info('User survey updated successfully', { userId: req.user.id });
 
+			void InternalHooksManager.getInstance().onPersonalizationSurveySubmitted(
+				req.user.id,
+				personalizationAnswers,
+			);
+
 			return { success: true };
 		}),
 	);
diff --git a/packages/cli/src/UserManagement/routes/owner.ts b/packages/cli/src/UserManagement/routes/owner.ts
index 0ece05e8a870c..a526afc948a9f 100644
--- a/packages/cli/src/UserManagement/routes/owner.ts
+++ b/packages/cli/src/UserManagement/routes/owner.ts
@@ -5,7 +5,7 @@ import * as express from 'express';
 import validator from 'validator';
 import { LoggerProxy as Logger } from 'n8n-workflow';
 
-import { Db, ResponseHelper } from '../..';
+import { Db, InternalHooksManager, ResponseHelper } from '../..';
 import config = require('../../../config');
 import { validateEntity } from '../../GenericHelpers';
 import { AuthenticatedRequest, OwnerRequest } from '../../requests';
@@ -94,6 +94,10 @@ export function ownerNamespace(this: N8nApp): void {
 
 			await issueCookie(res, owner);
 
+			void InternalHooksManager.getInstance().onInstanceOwnerSetup({
+				user_id: userId,
+			});
+
 			return sanitizeUser(owner);
 		}),
 	);
diff --git a/packages/cli/src/UserManagement/routes/passwordReset.ts b/packages/cli/src/UserManagement/routes/passwordReset.ts
index 1a5b3aee74c3c..7dbb630283d30 100644
--- a/packages/cli/src/UserManagement/routes/passwordReset.ts
+++ b/packages/cli/src/UserManagement/routes/passwordReset.ts
@@ -9,7 +9,7 @@ import validator from 'validator';
 import { IsNull, MoreThanOrEqual, Not } from 'typeorm';
 import { LoggerProxy as Logger } from 'n8n-workflow';
 
-import { Db, ResponseHelper } from '../..';
+import { Db, InternalHooksManager, ResponseHelper } from '../..';
 import { N8nApp } from '../Interfaces';
 import { validatePassword } from '../UserManagementHelper';
 import * as UserManagementMailer from '../email';
@@ -98,6 +98,14 @@ export function passwordResetNamespace(this: N8nApp): void {
 			}
 
 			Logger.info('Sent password reset email successfully', { userId: user.id, email });
+			void InternalHooksManager.getInstance().onUserTransactionalEmail({
+				user_id: id,
+				message_type: 'Reset password',
+			});
+
+			void InternalHooksManager.getInstance().onUserPasswordResetRequestClick({
+				user_id: id,
+			});
 		}),
 	);
 
@@ -142,6 +150,9 @@ export function passwordResetNamespace(this: N8nApp): void {
 			}
 
 			Logger.info('Reset-password token resolved successfully', { userId: id });
+			void InternalHooksManager.getInstance().onUserPasswordResetEmailClick({
+				user_id: id,
+			});
 		}),
 	);
 
diff --git a/packages/cli/src/UserManagement/routes/users.ts b/packages/cli/src/UserManagement/routes/users.ts
index 2b649d01cee05..a91b0cfa52dc8 100644
--- a/packages/cli/src/UserManagement/routes/users.ts
+++ b/packages/cli/src/UserManagement/routes/users.ts
@@ -7,7 +7,7 @@ import { genSaltSync, hashSync } from 'bcryptjs';
 import validator from 'validator';
 import { LoggerProxy as Logger } from 'n8n-workflow';
 
-import { Db, ResponseHelper } from '../..';
+import { Db, InternalHooksManager, ITelemetryUserDeletionData, ResponseHelper } from '../..';
 import { N8nApp, PublicUser } from '../Interfaces';
 import { UserRequest } from '../../requests';
 import { getInstanceBaseUrl, sanitizeUser, validatePassword } from '../UserManagementHelper';
@@ -139,6 +139,11 @@ export function usersNamespace(this: N8nApp): void {
 						}),
 					);
 				});
+
+				void InternalHooksManager.getInstance().onUserInvite({
+					user_id: req.user.id,
+					target_user_id: Object.values(createUsers) as string[],
+				});
 			} catch (error) {
 				Logger.error('Failed to create user shells', { userShells: createUsers });
 				throw new ResponseHelper.ResponseError('An error occurred during user creation');
@@ -170,7 +175,12 @@ export function usersNamespace(this: N8nApp): void {
 							email,
 						},
 					};
-					if (!result?.success) {
+					if (result?.success) {
+						void InternalHooksManager.getInstance().onUserTransactionalEmail({
+							user_id: id!,
+							message_type: 'New user invite',
+						});
+					} else {
 						Logger.error('Failed to send email', {
 							userId: req.user.id,
 							inviteAcceptUrl,
@@ -254,6 +264,10 @@ export function usersNamespace(this: N8nApp): void {
 				throw new ResponseHelper.ResponseError('Invalid request', undefined, 400);
 			}
 
+			void InternalHooksManager.getInstance().onUserInviteEmailClick({
+				user_id: inviteeId,
+			});
+
 			const { firstName, lastName } = inviter;
 
 			return { inviter: { firstName, lastName } };
@@ -320,6 +334,10 @@ export function usersNamespace(this: N8nApp): void {
 
 			await issueCookie(res, updatedUser);
 
+			void InternalHooksManager.getInstance().onUserSignup({
+				user_id: invitee.id,
+			});
+
 			return sanitizeUser(updatedUser);
 		}),
 	);
@@ -420,6 +438,20 @@ export function usersNamespace(this: N8nApp): void {
 				await transactionManager.delete(User, { id: userToDelete.id });
 			});
 
+			const telemetryData: ITelemetryUserDeletionData = {
+				user_id: req.user.id,
+				target_user_old_status: userToDelete.isPending ? 'invited' : 'active',
+				target_user_id: idToDelete,
+			};
+
+			telemetryData.migration_strategy = transferId ? 'transfer_data' : 'delete_data';
+
+			if (transferId) {
+				telemetryData.migration_user_id = transferId;
+			}
+
+			void InternalHooksManager.getInstance().onUserDeletion(req.user.id, telemetryData);
+
 			return { success: true };
 		}),
 	);
@@ -495,6 +527,16 @@ export function usersNamespace(this: N8nApp): void {
 				);
 			}
 
+			void InternalHooksManager.getInstance().onUserReinvite({
+				user_id: req.user.id,
+				target_user_id: reinvitee.id,
+			});
+
+			void InternalHooksManager.getInstance().onUserTransactionalEmail({
+				user_id: reinvitee.id,
+				message_type: 'Resend invite',
+			});
+
 			return { success: true };
 		}),
 	);
diff --git a/packages/cli/src/WorkflowExecuteAdditionalData.ts b/packages/cli/src/WorkflowExecuteAdditionalData.ts
index 0b0d4ec004870..ee2b2277444cd 100644
--- a/packages/cli/src/WorkflowExecuteAdditionalData.ts
+++ b/packages/cli/src/WorkflowExecuteAdditionalData.ts
@@ -967,7 +967,12 @@ export async function executeWorkflow(
 	}
 
 	await externalHooks.run('workflow.postExecute', [data, workflowData, executionId]);
-	void InternalHooksManager.getInstance().onWorkflowPostExecute(executionId, workflowData, data);
+	void InternalHooksManager.getInstance().onWorkflowPostExecute(
+		executionId,
+		workflowData,
+		data,
+		additionalData.userId,
+	);
 
 	if (data.finished === true) {
 		// Workflow did finish successfully
diff --git a/packages/cli/src/WorkflowRunner.ts b/packages/cli/src/WorkflowRunner.ts
index c6c86b841de45..6d4abbaaaf957 100644
--- a/packages/cli/src/WorkflowRunner.ts
+++ b/packages/cli/src/WorkflowRunner.ts
@@ -178,6 +178,7 @@ export class WorkflowRunner {
 					executionId!,
 					data.workflowData,
 					executionData,
+					data.userId,
 				);
 			})
 			.catch((error) => {
diff --git a/packages/cli/src/WorkflowRunnerProcess.ts b/packages/cli/src/WorkflowRunnerProcess.ts
index 44317b851fa6d..8c2d457c4feef 100644
--- a/packages/cli/src/WorkflowRunnerProcess.ts
+++ b/packages/cli/src/WorkflowRunnerProcess.ts
@@ -311,6 +311,7 @@ export class WorkflowRunnerProcess {
 					executionId,
 					workflowData,
 					result,
+					additionalData.userId,
 				);
 				await sendToParentProcess('finishExecution', { executionId, result });
 				delete this.childExecutions[executionId];
diff --git a/packages/cli/src/requests.d.ts b/packages/cli/src/requests.d.ts
index bfa21565784c9..72e1ffe0e29d3 100644
--- a/packages/cli/src/requests.d.ts
+++ b/packages/cli/src/requests.d.ts
@@ -14,6 +14,13 @@ import { User } from './databases/entities/User';
 import type { IExecutionDeleteFilter, IWorkflowDb } from '.';
 import type { PublicUser } from './UserManagement/Interfaces';
 
+export type AuthlessRequest<
+	RouteParams = {},
+	ResponseBody = {},
+	RequestBody = {},
+	RequestQuery = {},
+> = express.Request<RouteParams, ResponseBody, RequestBody, RequestQuery>;
+
 export type AuthenticatedRequest<
 	RouteParams = {},
 	ResponseBody = {},
@@ -159,11 +166,11 @@ export declare namespace OwnerRequest {
 // ----------------------------------
 
 export declare namespace PasswordResetRequest {
-	export type Email = AuthenticatedRequest<{}, {}, Pick<PublicUser, 'email'>>;
+	export type Email = AuthlessRequest<{}, {}, Pick<PublicUser, 'email'>>;
 
-	export type Credentials = AuthenticatedRequest<{}, {}, {}, { userId?: string; token?: string }>;
+	export type Credentials = AuthlessRequest<{}, {}, {}, { userId?: string; token?: string }>;
 
-	export type NewPassword = AuthenticatedRequest<
+	export type NewPassword = AuthlessRequest<
 		{},
 		{},
 		Pick<PublicUser, 'password'> & { token?: string; userId?: string }
@@ -177,7 +184,7 @@ export declare namespace PasswordResetRequest {
 export declare namespace UserRequest {
 	export type Invite = AuthenticatedRequest<{}, {}, Array<{ email: string }>>;
 
-	export type ResolveSignUp = AuthenticatedRequest<
+	export type ResolveSignUp = AuthlessRequest<
 		{},
 		{},
 		{},
@@ -193,7 +200,7 @@ export declare namespace UserRequest {
 
 	export type Reinvite = AuthenticatedRequest<{ id: string }>;
 
-	export type Update = AuthenticatedRequest<
+	export type Update = AuthlessRequest<
 		{ id: string },
 		{},
 		{
@@ -205,6 +212,19 @@ export declare namespace UserRequest {
 	>;
 }
 
+// ----------------------------------
+//             /login
+// ----------------------------------
+
+export type LoginRequest = AuthlessRequest<
+	{},
+	{},
+	{
+		email: string;
+		password: string;
+	}
+>;
+
 // ----------------------------------
 //          oauth endpoints
 // ----------------------------------
diff --git a/packages/cli/src/telemetry/index.ts b/packages/cli/src/telemetry/index.ts
index 6b678f099fe60..69a4bad45617f 100644
--- a/packages/cli/src/telemetry/index.ts
+++ b/packages/cli/src/telemetry/index.ts
@@ -1,3 +1,4 @@
+/* eslint-disable import/no-cycle */
 /* eslint-disable @typescript-eslint/no-unsafe-call */
 /* eslint-disable @typescript-eslint/no-unsafe-member-access */
 import TelemetryClient = require('@rudderstack/rudder-sdk-node');
@@ -184,12 +185,17 @@ export class Telemetry {
 		});
 	}
 
-	async track(eventName: string, properties?: IDataObject): Promise<void> {
+	async track(
+		eventName: string,
+		properties: { [key: string]: unknown; user_id?: string } = {},
+	): Promise<void> {
 		return new Promise<void>((resolve) => {
 			if (this.client) {
+				const { user_id } = properties;
+				Object.assign(properties, { instance_id: this.instanceId });
 				this.client.track(
 					{
-						userId: this.instanceId,
+						userId: `${this.instanceId}${user_id ? `#${user_id}` : ''}`,
 						anonymousId: '000000000000',
 						event: eventName,
 						properties,
diff --git a/packages/cli/test/integration/auth.endpoints.test.ts b/packages/cli/test/integration/auth.endpoints.test.ts
index a29504a1b648e..23ef7e3e3d6f5 100644
--- a/packages/cli/test/integration/auth.endpoints.test.ts
+++ b/packages/cli/test/integration/auth.endpoints.test.ts
@@ -26,6 +26,7 @@ beforeAll(async () => {
 
 	globalOwnerRole = await getGlobalOwnerRole();
 	utils.initTestLogger();
+	utils.initTestTelemetry();
 });
 
 beforeEach(async () => {
diff --git a/packages/cli/test/integration/auth.middleware.test.ts b/packages/cli/test/integration/auth.middleware.test.ts
index 3dfb6685ad201..d686496aab2b2 100644
--- a/packages/cli/test/integration/auth.middleware.test.ts
+++ b/packages/cli/test/integration/auth.middleware.test.ts
@@ -20,6 +20,7 @@ beforeAll(async () => {
 	const initResult = await testDb.init();
 	testDbName = initResult.testDbName;
 	utils.initTestLogger();
+	utils.initTestTelemetry();
 });
 
 afterAll(async () => {
diff --git a/packages/cli/test/integration/credentials.api.test.ts b/packages/cli/test/integration/credentials.api.test.ts
index c1a3737f86ff4..533660ff57a19 100644
--- a/packages/cli/test/integration/credentials.api.test.ts
+++ b/packages/cli/test/integration/credentials.api.test.ts
@@ -24,6 +24,7 @@ beforeAll(async () => {
 
 	const credentialOwnerRole = await testDb.getCredentialOwnerRole();
 	saveCredential = affixRoleToSaveCredential(credentialOwnerRole);
+	utils.initTestTelemetry();
 });
 
 beforeEach(async () => {
diff --git a/packages/cli/test/integration/me.endpoints.test.ts b/packages/cli/test/integration/me.endpoints.test.ts
index 0da438d5c6895..ca86b85818435 100644
--- a/packages/cli/test/integration/me.endpoints.test.ts
+++ b/packages/cli/test/integration/me.endpoints.test.ts
@@ -21,6 +21,7 @@ beforeAll(async () => {
 
 	globalOwnerRole = await testDb.getGlobalOwnerRole();
 	utils.initTestLogger();
+	utils.initTestTelemetry();
 });
 
 afterAll(async () => {
diff --git a/packages/cli/test/integration/owner.endpoints.test.ts b/packages/cli/test/integration/owner.endpoints.test.ts
index f4313301174f9..74e6ba377793c 100644
--- a/packages/cli/test/integration/owner.endpoints.test.ts
+++ b/packages/cli/test/integration/owner.endpoints.test.ts
@@ -21,6 +21,7 @@ beforeAll(async () => {
 	testDbName = initResult.testDbName;
 
 	utils.initTestLogger();
+	utils.initTestTelemetry();
 });
 
 beforeEach(async () => {
diff --git a/packages/cli/test/integration/passwordReset.endpoints.test.ts b/packages/cli/test/integration/passwordReset.endpoints.test.ts
index 8cb3ef0cc7289..36dd7d8261c58 100644
--- a/packages/cli/test/integration/passwordReset.endpoints.test.ts
+++ b/packages/cli/test/integration/passwordReset.endpoints.test.ts
@@ -29,6 +29,8 @@ beforeAll(async () => {
 		name: 'owner',
 		scope: 'global',
 	});
+
+	utils.initTestTelemetry();
 	utils.initTestLogger();
 });
 
diff --git a/packages/cli/test/integration/shared/utils.ts b/packages/cli/test/integration/shared/utils.ts
index 7cbceb19861b8..45f97cfabf6ad 100644
--- a/packages/cli/test/integration/shared/utils.ts
+++ b/packages/cli/test/integration/shared/utils.ts
@@ -7,14 +7,14 @@ import { URL } from 'url';
 import bodyParser = require('body-parser');
 import * as util from 'util';
 import { createTestAccount } from 'nodemailer';
-import { LoggerProxy } from 'n8n-workflow';
+import { INodeTypes, LoggerProxy } from 'n8n-workflow';
 import { UserSettings } from 'n8n-core';
 
 import config = require('../../../config');
 import { AUTHLESS_ENDPOINTS, REST_PATH_SEGMENT } from './constants';
 import { AUTH_COOKIE_NAME } from '../../../src/constants';
 import { addRoutes as authMiddleware } from '../../../src/UserManagement/routes';
-import { Db, ExternalHooks } from '../../../src';
+import { Db, ExternalHooks, InternalHooksManager } from '../../../src';
 import { meNamespace as meEndpoints } from '../../../src/UserManagement/routes/me';
 import { usersNamespace as usersEndpoints } from '../../../src/UserManagement/routes/users';
 import { authenticationMethods as authEndpoints } from '../../../src/UserManagement/routes/auth';
@@ -25,6 +25,7 @@ import { getLogger } from '../../../src/Logger';
 import { credentialsController } from '../../../src/api/credentials.api';
 
 import type { User } from '../../../src/databases/entities/User';
+import { Telemetry } from '../../../src/telemetry';
 import type { EndpointGroup, SmtpTestAccount } from './types';
 import type { N8nApp } from '../../../src/UserManagement/Interfaces';
 
@@ -88,6 +89,14 @@ export function initTestServer({
 	return testServer.app;
 }
 
+export function initTestTelemetry() {
+	const mockNodeTypes = { nodeTypes: {} } as INodeTypes;
+
+	void InternalHooksManager.init('test-instance-id', 'test-version', mockNodeTypes);
+
+	jest.spyOn(Telemetry.prototype, 'track').mockResolvedValue();
+}
+
 /**
  * Classify endpoint groups into `routerEndpoints` (newest, using `express.Router`),
  * and `functionEndpoints` (legacy, namespaced inside a function).
diff --git a/packages/cli/test/integration/users.endpoints.test.ts b/packages/cli/test/integration/users.endpoints.test.ts
index 6e5b673678379..d1eaee700bdb2 100644
--- a/packages/cli/test/integration/users.endpoints.test.ts
+++ b/packages/cli/test/integration/users.endpoints.test.ts
@@ -42,6 +42,7 @@ beforeAll(async () => {
 	workflowOwnerRole = fetchedWorkflowOwnerRole;
 	credentialOwnerRole = fetchedCredentialOwnerRole;
 
+	utils.initTestTelemetry();
 	utils.initTestLogger();
 });