diff --git a/packages/cli/src/AbstractServer.ts b/packages/cli/src/AbstractServer.ts
index 55eae9376a520..10bebc44b819f 100644
--- a/packages/cli/src/AbstractServer.ts
+++ b/packages/cli/src/AbstractServer.ts
@@ -159,33 +159,17 @@ export abstract class AbstractServer {
 	protected setupPushServer() {}
 
 	private async setupHealthCheck() {
-		this.app.use((req, res, next) => {
-			if (!Db.isInitialized) {
-				sendErrorResponse(res, new ServiceUnavailableError('Database is not ready!'));
-			} else next();
-		});
-
-		// Does very basic health check
+		// health check should not care about DB connections
 		this.app.get('/healthz', async (req, res) => {
-			Logger.debug('Health check started!');
-
-			const connection = Db.getConnection();
-
-			try {
-				if (!connection.isInitialized) {
-					// Connection is not active
-					throw new ServiceUnavailableError('No active database connection!');
-				}
-				// DB ping
-				await connection.query('SELECT 1');
-			} catch (error) {
-				ErrorReporter.error(error);
-				Logger.error('No Database connection!');
-				return sendErrorResponse(res, new ServiceUnavailableError('No Database connection!'));
-			}
+			res.send({ status: 'ok' });
+		});
 
-			Logger.debug('Health check completed successfully!');
-			sendSuccessResponse(res, { status: 'ok' }, true, 200);
+		const { connectionState } = Db;
+		this.app.use((req, res, next) => {
+			if (connectionState.connected) {
+				if (connectionState.migrated) next();
+				else res.send('n8n is starting up. Please wait');
+			} else sendErrorResponse(res, new ServiceUnavailableError('Database is not ready!'));
 		});
 
 		if (config.getEnv('executions.mode') === 'queue') {
@@ -400,8 +384,8 @@ export abstract class AbstractServer {
 		);
 	}
 
-	async start(): Promise<void> {
-		const { app, externalHooks, protocol, sslKey, sslCert } = this;
+	async init(): Promise<void> {
+		const { app, protocol, sslKey, sslCert } = this;
 
 		if (protocol === 'https' && sslKey && sslCert) {
 			const https = await import('https');
@@ -431,6 +415,12 @@ export abstract class AbstractServer {
 
 		await new Promise<void>((resolve) => this.server.listen(PORT, ADDRESS, () => resolve()));
 
+		await this.setupHealthCheck();
+
+		console.log(`n8n ready on ${ADDRESS}, port ${PORT}`);
+	}
+
+	async start(): Promise<void> {
 		await this.setupErrorHandlers();
 		this.setupPushServer();
 		await this.setupCommonMiddlewares();
@@ -438,11 +428,7 @@ export abstract class AbstractServer {
 			this.setupDevMiddlewares();
 		}
 
-		await this.setupHealthCheck();
-
 		await this.configure();
-
-		console.log(`n8n ready on ${ADDRESS}, port ${PORT}`);
 		console.log(`Version: ${N8N_VERSION}`);
 
 		const defaultLocale = config.getEnv('defaultLocale');
@@ -450,7 +436,7 @@ export abstract class AbstractServer {
 			console.log(`Locale: ${defaultLocale}`);
 		}
 
-		await externalHooks.run('n8n.ready', [this, config]);
+		await this.externalHooks.run('n8n.ready', [this, config]);
 	}
 }
 
diff --git a/packages/cli/src/CredentialsHelper.ts b/packages/cli/src/CredentialsHelper.ts
index cfc86bfd263af..5b20ff91b267d 100644
--- a/packages/cli/src/CredentialsHelper.ts
+++ b/packages/cli/src/CredentialsHelper.ts
@@ -453,12 +453,6 @@ export class CredentialsHelper extends ICredentialsHelper {
 	): Promise<void> {
 		const credentials = await this.getCredentials(nodeCredentials, type);
 
-		if (!Db.isInitialized) {
-			// The first time executeWorkflow gets called the Database has
-			// to get initialized first
-			await Db.init();
-		}
-
 		credentials.setData(data, this.encryptionKey);
 		const newCredentialsData = credentials.getDataToSave() as ICredentialsDb;
 
diff --git a/packages/cli/src/Db.ts b/packages/cli/src/Db.ts
index 114aa22a3116f..af274427e2fd7 100644
--- a/packages/cli/src/Db.ts
+++ b/packages/cli/src/Db.ts
@@ -7,6 +7,8 @@ import { Container } from 'typedi';
 import type { DataSourceOptions as ConnectionOptions, EntityManager, LoggerOptions } from 'typeorm';
 import { DataSource as Connection } from 'typeorm';
 import type { TlsOptions } from 'tls';
+import { ErrorReporterProxy as ErrorReporter } from 'n8n-workflow';
+
 import type { IDatabaseCollections } from '@/Interfaces';
 
 import config from '@/config';
@@ -19,6 +21,7 @@ import {
 	getPostgresConnectionOptions,
 	getSqliteConnectionOptions,
 } from '@db/config';
+import { inTest } from '@/constants';
 import { wrapMigration } from '@db/utils/migrationHelpers';
 import type { DatabaseType, Migration } from '@db/types';
 import {
@@ -43,13 +46,42 @@ import {
 	WorkflowTagMappingRepository,
 } from '@db/repositories';
 
-export let isInitialized = false;
 export const collections = {} as IDatabaseCollections;
 
 let connection: Connection;
 
 export const getConnection = () => connection!;
 
+type ConnectionState = {
+	connected: boolean;
+	migrated: boolean;
+};
+
+export const connectionState: ConnectionState = {
+	connected: false,
+	migrated: false,
+};
+
+// Ping DB connection every 2 seconds
+let pingTimer: NodeJS.Timer | undefined;
+if (!inTest) {
+	const pingDBFn = async () => {
+		if (connection?.isInitialized) {
+			try {
+				await connection.query('SELECT 1');
+				connectionState.connected = true;
+				return;
+			} catch (error) {
+				ErrorReporter.error(error);
+			} finally {
+				pingTimer = setTimeout(pingDBFn, 2000);
+			}
+		}
+		connectionState.connected = false;
+	};
+	pingTimer = setTimeout(pingDBFn, 2000);
+}
+
 export async function transaction<T>(fn: (entityManager: EntityManager) => Promise<T>): Promise<T> {
 	return connection.transaction(fn);
 }
@@ -94,10 +126,14 @@ export function getConnectionOptions(dbType: DatabaseType): ConnectionOptions {
 	}
 }
 
-export async function init(
-	testConnectionOptions?: ConnectionOptions,
-): Promise<IDatabaseCollections> {
-	if (isInitialized) return collections;
+const openConnection = async (options: ConnectionOptions) => {
+	connection = new Connection(options);
+	await connection.initialize();
+	Container.set(Connection, connection);
+};
+
+export async function init(testConnectionOptions?: ConnectionOptions): Promise<void> {
+	if (connectionState.connected) return;
 
 	const dbType = config.getEnv('database.type');
 	const connectionOptions = testConnectionOptions ?? getConnectionOptions(dbType);
@@ -124,9 +160,7 @@ export async function init(
 		migrationsRun: false,
 	});
 
-	connection = new Connection(connectionOptions);
-	Container.set(Connection, connection);
-	await connection.initialize();
+	await openConnection(connectionOptions);
 
 	if (dbType === 'postgresdb') {
 		const schema = config.getEnv('database.postgresdb.schema');
@@ -138,9 +172,13 @@ export async function init(
 		await connection.query(`SET search_path TO ${searchPath.join(',')};`);
 	}
 
-	(connectionOptions.migrations as Migration[]).forEach(wrapMigration);
+	connectionState.connected = true;
+}
+
+export async function migrate() {
+	(connection.options.migrations as Migration[]).forEach(wrapMigration);
 
-	if (!testConnectionOptions && dbType === 'sqlite') {
+	if (!inTest && connection.options.type === 'sqlite') {
 		// This specific migration changes database metadata.
 		// A field is now nullable. We need to reconnect so that
 		// n8n knows it has changed. Happens only on sqlite.
@@ -161,9 +199,7 @@ export async function init(
 		// eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
 		if (migrations.length === 0) {
 			await connection.destroy();
-			connection = new Connection(connectionOptions);
-			Container.set(Connection, connection);
-			await connection.initialize();
+			await openConnection(connection.options);
 		}
 	} else {
 		await connection.runMigrations({ transaction: 'each' });
@@ -189,7 +225,14 @@ export async function init(
 	collections.WorkflowStatistics = Container.get(WorkflowStatisticsRepository);
 	collections.WorkflowTagMapping = Container.get(WorkflowTagMappingRepository);
 
-	isInitialized = true;
-
-	return collections;
+	connectionState.migrated = true;
 }
+
+export const close = async () => {
+	if (pingTimer) {
+		clearTimeout(pingTimer);
+		pingTimer = undefined;
+	}
+
+	if (connection.isInitialized) await connection.destroy();
+};
diff --git a/packages/cli/src/Server.ts b/packages/cli/src/Server.ts
index ddaf2a6f9093a..f5406d2b2d212 100644
--- a/packages/cli/src/Server.ts
+++ b/packages/cli/src/Server.ts
@@ -170,7 +170,7 @@ import { VersionControlController } from '@/environments/versionControl/versionC
 
 const exec = promisify(callbackExec);
 
-class Server extends AbstractServer {
+export class Server extends AbstractServer {
 	endpointPresetCredentials: string;
 
 	waitTracker: WaitTracker;
@@ -198,23 +198,6 @@ class Server extends AbstractServer {
 		this.app.set('view engine', 'handlebars');
 		this.app.set('views', TEMPLATES_DIR);
 
-		this.loadNodesAndCredentials = Container.get(LoadNodesAndCredentials);
-		this.credentialTypes = Container.get(CredentialTypes);
-		this.nodeTypes = Container.get(NodeTypes);
-
-		this.activeExecutionsInstance = Container.get(ActiveExecutions);
-		this.waitTracker = Container.get(WaitTracker);
-		this.postHog = Container.get(PostHogClient);
-
-		this.presetCredentialsLoaded = false;
-		this.endpointPresetCredentials = config.getEnv('credentials.overwrite.endpoint');
-
-		this.push = Container.get(Push);
-
-		if (process.env.E2E_TESTS === 'true') {
-			this.app.use('/e2e', require('./api/e2e.api').e2eController);
-		}
-
 		const urlBaseWebhook = WebhookHelpers.getWebhookBaseUrl();
 		const telemetrySettings: ITelemetrySettings = {
 			enabled: config.getEnv('diagnostics.enabled'),
@@ -339,6 +322,88 @@ class Server extends AbstractServer {
 		};
 	}
 
+	async start() {
+		this.loadNodesAndCredentials = Container.get(LoadNodesAndCredentials);
+		this.credentialTypes = Container.get(CredentialTypes);
+		this.nodeTypes = Container.get(NodeTypes);
+
+		this.activeExecutionsInstance = Container.get(ActiveExecutions);
+		this.waitTracker = Container.get(WaitTracker);
+		this.postHog = Container.get(PostHogClient);
+
+		this.presetCredentialsLoaded = false;
+		this.endpointPresetCredentials = config.getEnv('credentials.overwrite.endpoint');
+
+		this.push = Container.get(Push);
+
+		if (process.env.E2E_TESTS === 'true') {
+			this.app.use('/e2e', require('./api/e2e.api').e2eController);
+		}
+
+		await super.start();
+
+		const cpus = os.cpus();
+		const binaryDataConfig = config.getEnv('binaryDataManager');
+		const diagnosticInfo: IDiagnosticInfo = {
+			basicAuthActive: config.getEnv('security.basicAuth.active'),
+			databaseType: config.getEnv('database.type'),
+			disableProductionWebhooksOnMainProcess: config.getEnv(
+				'endpoints.disableProductionWebhooksOnMainProcess',
+			),
+			notificationsEnabled: config.getEnv('versionNotifications.enabled'),
+			versionCli: N8N_VERSION,
+			systemInfo: {
+				os: {
+					type: os.type(),
+					version: os.version(),
+				},
+				memory: os.totalmem() / 1024,
+				cpus: {
+					count: cpus.length,
+					model: cpus[0].model,
+					speed: cpus[0].speed,
+				},
+			},
+			executionVariables: {
+				executions_process: config.getEnv('executions.process'),
+				executions_mode: config.getEnv('executions.mode'),
+				executions_timeout: config.getEnv('executions.timeout'),
+				executions_timeout_max: config.getEnv('executions.maxTimeout'),
+				executions_data_save_on_error: config.getEnv('executions.saveDataOnError'),
+				executions_data_save_on_success: config.getEnv('executions.saveDataOnSuccess'),
+				executions_data_save_on_progress: config.getEnv('executions.saveExecutionProgress'),
+				executions_data_save_manual_executions: config.getEnv(
+					'executions.saveDataManualExecutions',
+				),
+				executions_data_prune: config.getEnv('executions.pruneData'),
+				executions_data_max_age: config.getEnv('executions.pruneDataMaxAge'),
+				executions_data_prune_timeout: config.getEnv('executions.pruneDataTimeout'),
+			},
+			deploymentType: config.getEnv('deployment.type'),
+			binaryDataMode: binaryDataConfig.mode,
+			n8n_multi_user_allowed: isUserManagementEnabled(),
+			smtp_set_up: config.getEnv('userManagement.emails.mode') === 'smtp',
+			ldap_allowed: isLdapCurrentAuthenticationMethod(),
+			saml_enabled: isSamlCurrentAuthenticationMethod(),
+		};
+
+		// Set up event handling
+		initEvents();
+
+		if (inDevelopment && process.env.N8N_DEV_RELOAD === 'true') {
+			const { reloadNodesAndCredentials } = await import('@/ReloadNodesAndCredentials');
+			await reloadNodesAndCredentials(this.loadNodesAndCredentials, this.nodeTypes, this.push);
+		}
+
+		void Db.collections.Workflow.findOne({
+			select: ['createdAt'],
+			order: { createdAt: 'ASC' },
+			where: {},
+		}).then(async (workflow) =>
+			Container.get(InternalHooks).onServerStarted(diagnosticInfo, workflow?.createdAt),
+		);
+	}
+
 	/**
 	 * Returns the current settings for the frontend
 	 */
@@ -1379,67 +1444,3 @@ class Server extends AbstractServer {
 		setupPushServer(restEndpoint, server, app);
 	}
 }
-
-export async function start(): Promise<void> {
-	const app = new Server();
-	await app.start();
-
-	const cpus = os.cpus();
-	const binaryDataConfig = config.getEnv('binaryDataManager');
-	const diagnosticInfo: IDiagnosticInfo = {
-		basicAuthActive: config.getEnv('security.basicAuth.active'),
-		databaseType: config.getEnv('database.type'),
-		disableProductionWebhooksOnMainProcess: config.getEnv(
-			'endpoints.disableProductionWebhooksOnMainProcess',
-		),
-		notificationsEnabled: config.getEnv('versionNotifications.enabled'),
-		versionCli: N8N_VERSION,
-		systemInfo: {
-			os: {
-				type: os.type(),
-				version: os.version(),
-			},
-			memory: os.totalmem() / 1024,
-			cpus: {
-				count: cpus.length,
-				model: cpus[0].model,
-				speed: cpus[0].speed,
-			},
-		},
-		executionVariables: {
-			executions_process: config.getEnv('executions.process'),
-			executions_mode: config.getEnv('executions.mode'),
-			executions_timeout: config.getEnv('executions.timeout'),
-			executions_timeout_max: config.getEnv('executions.maxTimeout'),
-			executions_data_save_on_error: config.getEnv('executions.saveDataOnError'),
-			executions_data_save_on_success: config.getEnv('executions.saveDataOnSuccess'),
-			executions_data_save_on_progress: config.getEnv('executions.saveExecutionProgress'),
-			executions_data_save_manual_executions: config.getEnv('executions.saveDataManualExecutions'),
-			executions_data_prune: config.getEnv('executions.pruneData'),
-			executions_data_max_age: config.getEnv('executions.pruneDataMaxAge'),
-			executions_data_prune_timeout: config.getEnv('executions.pruneDataTimeout'),
-		},
-		deploymentType: config.getEnv('deployment.type'),
-		binaryDataMode: binaryDataConfig.mode,
-		n8n_multi_user_allowed: isUserManagementEnabled(),
-		smtp_set_up: config.getEnv('userManagement.emails.mode') === 'smtp',
-		ldap_allowed: isLdapCurrentAuthenticationMethod(),
-		saml_enabled: isSamlCurrentAuthenticationMethod(),
-	};
-
-	// Set up event handling
-	initEvents();
-
-	if (inDevelopment && process.env.N8N_DEV_RELOAD === 'true') {
-		const { reloadNodesAndCredentials } = await import('@/ReloadNodesAndCredentials');
-		await reloadNodesAndCredentials(app.loadNodesAndCredentials, app.nodeTypes, app.push);
-	}
-
-	void Db.collections.Workflow.findOne({
-		select: ['createdAt'],
-		order: { createdAt: 'ASC' },
-		where: {},
-	}).then(async (workflow) =>
-		Container.get(InternalHooks).onServerStarted(diagnosticInfo, workflow?.createdAt),
-	);
-}
diff --git a/packages/cli/src/WorkflowExecuteAdditionalData.ts b/packages/cli/src/WorkflowExecuteAdditionalData.ts
index 9cc7aac265e1a..f19278700b86f 100644
--- a/packages/cli/src/WorkflowExecuteAdditionalData.ts
+++ b/packages/cli/src/WorkflowExecuteAdditionalData.ts
@@ -927,12 +927,6 @@ export async function getWorkflowData(
 
 	let workflowData: IWorkflowBase | null;
 	if (workflowInfo.id !== undefined) {
-		if (!Db.isInitialized) {
-			// The first time executeWorkflow gets called the Database has
-			// to get initialized first
-			await Db.init();
-		}
-
 		const relations = config.getEnv('workflowTagsDisabled') ? [] : ['tags'];
 
 		workflowData = await WorkflowsService.get({ id: workflowInfo.id }, { relations });
diff --git a/packages/cli/src/commands/BaseCommand.ts b/packages/cli/src/commands/BaseCommand.ts
index 2bd7a88572f3b..e629458b91b1a 100644
--- a/packages/cli/src/commands/BaseCommand.ts
+++ b/packages/cli/src/commands/BaseCommand.ts
@@ -5,6 +5,7 @@ import type { INodeTypes } from 'n8n-workflow';
 import { LoggerProxy, ErrorReporterProxy as ErrorReporter, sleep } from 'n8n-workflow';
 import type { IUserSettings } from 'n8n-core';
 import { BinaryDataManager, UserSettings } from 'n8n-core';
+import type { AbstractServer } from '@/AbstractServer';
 import { getLogger } from '@/Logger';
 import config from '@/config';
 import * as Db from '@/Db';
@@ -36,6 +37,8 @@ export abstract class BaseCommand extends Command {
 
 	protected instanceId: string;
 
+	protected server?: AbstractServer;
+
 	async init(): Promise<void> {
 		await initErrorHandling();
 
@@ -55,6 +58,12 @@ export abstract class BaseCommand extends Command {
 			this.exitWithCrash('There was an error initializing DB', error),
 		);
 
+		await this.server?.init();
+
+		await Db.migrate().catch(async (error: Error) =>
+			this.exitWithCrash('There was an error running database migrations', error),
+		);
+
 		if (process.env.WEBHOOK_TUNNEL_URL) {
 			LoggerProxy.warn(
 				'You are still using the WEBHOOK_TUNNEL_URL environment variable. It has been deprecated and will be removed in a future version of n8n. Please switch to using WEBHOOK_URL instead.',
@@ -112,9 +121,9 @@ export abstract class BaseCommand extends Command {
 
 	async finally(error: Error | undefined) {
 		if (inTest || this.id === 'start') return;
-		if (Db.isInitialized) {
+		if (Db.connectionState.connected) {
 			await sleep(100); // give any in-flight query some time to finish
-			await Db.getConnection().destroy();
+			await Db.close();
 		}
 		const exitCode = error instanceof ExitError ? error.oclif.exit : error ? 1 : 0;
 		this.exit(exitCode);
diff --git a/packages/cli/src/commands/start.ts b/packages/cli/src/commands/start.ts
index 358d8091eb692..016fc48a9ef1b 100644
--- a/packages/cli/src/commands/start.ts
+++ b/packages/cli/src/commands/start.ts
@@ -21,7 +21,7 @@ import { ActiveExecutions } from '@/ActiveExecutions';
 import { ActiveWorkflowRunner } from '@/ActiveWorkflowRunner';
 import * as Db from '@/Db';
 import * as GenericHelpers from '@/GenericHelpers';
-import * as Server from '@/Server';
+import { Server } from '@/Server';
 import { TestWebhooks } from '@/TestWebhooks';
 import { getAllInstalledPackages } from '@/CommunityNodes/packageModel';
 import { EDITOR_UI_DIST_DIR, GENERATED_STATIC_DIR } from '@/constants';
@@ -62,6 +62,8 @@ export class Start extends BaseCommand {
 
 	protected activeWorkflowRunner: ActiveWorkflowRunner;
 
+	protected server = new Server();
+
 	/**
 	 * Opens the UI in browser
 	 */
@@ -208,6 +210,7 @@ export class Start extends BaseCommand {
 
 	async init() {
 		await this.initCrashJournal();
+
 		await super.init();
 		this.logger.info('Initializing n8n process');
 		this.activeWorkflowRunner = Container.get(ActiveWorkflowRunner);
@@ -351,7 +354,7 @@ export class Start extends BaseCommand {
 			);
 		}
 
-		await Server.start();
+		await this.server.start();
 
 		// Start to get active workflows and run their triggers
 		await this.activeWorkflowRunner.init();
diff --git a/packages/cli/src/commands/webhook.ts b/packages/cli/src/commands/webhook.ts
index cc1ac53b35389..da2fc44315ce6 100644
--- a/packages/cli/src/commands/webhook.ts
+++ b/packages/cli/src/commands/webhook.ts
@@ -16,6 +16,8 @@ export class Webhook extends BaseCommand {
 		help: flags.help({ char: 'h' }),
 	};
 
+	protected server = new WebhookServer();
+
 	/**
 	 * Stops n8n in a graceful way.
 	 * Make for example sure that all the webhooks from third party services
@@ -81,7 +83,7 @@ export class Webhook extends BaseCommand {
 
 	async run() {
 		await Container.get(Queue).init();
-		await new WebhookServer().start();
+		await this.server.start();
 		this.logger.info('Webhook listener waiting for requests.');
 
 		// Make sure that the process does not close
diff --git a/packages/cli/test/integration/shared/testDb.ts b/packages/cli/test/integration/shared/testDb.ts
index 5cc910367d6b9..08eb9fce2e9f8 100644
--- a/packages/cli/test/integration/shared/testDb.ts
+++ b/packages/cli/test/integration/shared/testDb.ts
@@ -58,7 +58,7 @@ export async function init() {
 
 	if (dbType === 'sqlite') {
 		// no bootstrap connection required
-		return Db.init(getSqliteOptions({ name: testDbName }));
+		await Db.init(getSqliteOptions({ name: testDbName }));
 	}
 
 	if (dbType === 'postgresdb') {
@@ -89,7 +89,7 @@ export async function init() {
 		await bootstrapPostgres.query(`CREATE DATABASE ${testDbName}`);
 		await bootstrapPostgres.destroy();
 
-		return Db.init(getDBOptions('postgres', testDbName));
+		await Db.init(getDBOptions('postgres', testDbName));
 	}
 
 	if (dbType === 'mysqldb') {
@@ -97,18 +97,17 @@ export async function init() {
 		await bootstrapMysql.query(`CREATE DATABASE ${testDbName}`);
 		await bootstrapMysql.destroy();
 
-		return Db.init(getDBOptions('mysql', testDbName));
+		await Db.init(getDBOptions('mysql', testDbName));
 	}
 
-	throw new Error(`Unrecognized DB type: ${dbType}`);
+	await Db.migrate();
 }
 
 /**
  * Drop test DB, closing bootstrap connection if existing.
  */
 export async function terminate() {
-	const connection = Db.getConnection();
-	if (connection.isInitialized) await connection.destroy();
+	await Db.close();
 }
 
 /**