diff --git a/node_modules/@wordpress/env/lib/commands/start.js b/node_modules/@wordpress/env/lib/commands/start.js
index db05b82..7b85ec3 100644
--- a/node_modules/@wordpress/env/lib/commands/start.js
+++ b/node_modules/@wordpress/env/lib/commands/start.js
@@ -207,28 +207,32 @@ module.exports = async function start( {
 	if ( shouldConfigureWp ) {
 		spinner.text = 'Configuring WordPress.';
 
-		try {
-			await checkDatabaseConnection( config );
-		} catch ( error ) {
-			// Wait 30 seconds for MySQL to accept connections.
-			await retry( () => checkDatabaseConnection( config ), {
-				times: 30,
-				delay: 1000,
-			} );
-
-			// It takes 3-4 seconds for MySQL to be ready after it starts accepting connections.
-			await sleep( 4000 );
-		}
+		const targetEnvironments = {
+			development: 'cli',
+			tests: 'tests-cli',
+		};
+		for ( const environment in targetEnvironments ) {
+			const cliContainer = targetEnvironments[environment];
+			try {
+				await checkDatabaseConnection( cliContainer, config );
+			} catch ( error ) {
+				// Wait 30 seconds for MySQL to accept connections.
+				await retry( () => checkDatabaseConnection( cliContainer, config ), {
+					times: 30,
+					delay: 1000,
+				} );
+
+				// It takes 3-4 seconds for MySQL to be ready after it starts accepting connections.
+				await sleep( 4000 );
+			}
 
-		// Retry WordPress installation in case MySQL *still* wasn't ready.
-		await Promise.all( [
-			retry( () => configureWordPress( 'development', config, spinner ), {
-				times: 2,
-			} ),
-			retry( () => configureWordPress( 'tests', config, spinner ), {
-				times: 2,
-			} ),
-		] );
+			// Retry WordPress installation in case MySQL *still* wasn't ready.
+			await Promise.all( [
+				retry( () => configureWordPress( environment, config, spinner ), {
+					times: 2,
+				} ),
+			] );
+		}
 
 		// Set the cache key once everything has been configured.
 		await setCache( CONFIG_CACHE_KEY, configHash, {
diff --git a/node_modules/@wordpress/env/lib/wordpress.js b/node_modules/@wordpress/env/lib/wordpress.js
index 8c08fb1..55de6e8 100644
--- a/node_modules/@wordpress/env/lib/wordpress.js
+++ b/node_modules/@wordpress/env/lib/wordpress.js
@@ -57,8 +57,8 @@ function isWPMajorMinorVersionLower( version, compareVersion ) {
  *
  * @param {WPConfig} config The wp-env config object.
  */
-async function checkDatabaseConnection( { dockerComposeConfigPath, debug } ) {
-	await dockerCompose.run( 'cli', 'wp db check', {
+async function checkDatabaseConnection( cliContainer, { dockerComposeConfigPath, debug } ) {
+	await dockerCompose.run( cliContainer, 'wp db check', {
 		config: dockerComposeConfigPath,
 		commandOptions: [ '--rm' ],
 		log: debug,