diff --git a/assets/dev-env.lando.template.yml.ejs b/assets/dev-env.lando.template.yml.ejs
index ccf72dfd0..bfcc12bed 100644
--- a/assets/dev-env.lando.template.yml.ejs
+++ b/assets/dev-env.lando.template.yml.ejs
@@ -73,7 +73,7 @@ services:
         devtools:
           condition: service_completed_successfully
         wordpress:
-          condition: service_started
+          condition: service_completed_successfully
 <% if ( muPlugins.mode == 'image' ) { %>
         vip-mu-plugins:
           condition: service_started
@@ -191,8 +191,6 @@ services:
     type: compose
     services:
       image: ghcr.io/automattic/vip-container-images/wordpress:<%= wordpress.tag %>
-#      command: /usr/local/bin/entrypoint.sh
-      command: sh -c "rsync -a --chown=www-data:www-data /wp/ /shared/; sleep infinity"
       volumes:
         - ./wordpress:/shared
         - type: volume
@@ -200,10 +198,8 @@ services:
           target: /scripts
           volume:
             nocopy: true
-#      environment:
-#        LANDO_NO_SCRIPTS: 1
-#        LANDO_NEEDS_EXEC: 1
-#    initOnly: true
+    initOnly: true
+    entrypoint: /usr/bin/rsync -a --chown=${LANDO_HOST_USER_ID}:${LANDO_HOST_GROUP_ID} /wp/ /shared/
 
 <% if ( muPlugins.mode == 'image' ) { %>
   vip-mu-plugins:
diff --git a/src/lib/dev-environment/dev-environment-lando.ts b/src/lib/dev-environment/dev-environment-lando.ts
index 026e976d1..479795094 100644
--- a/src/lib/dev-environment/dev-environment-lando.ts
+++ b/src/lib/dev-environment/dev-environment-lando.ts
@@ -7,7 +7,7 @@ import landoUtils, { type AppInfo } from 'lando/plugins/lando-core/lib/utils';
 import landoBuildTask from 'lando/plugins/lando-tooling/lib/build';
 import { lookup } from 'node:dns/promises';
 import { mkdir, rename } from 'node:fs/promises';
-import { tmpdir } from 'node:os';
+import { tmpdir, userInfo } from 'node:os';
 import path, { dirname } from 'node:path';
 import { satisfies } from 'semver';
 import xdgBasedir from 'xdg-basedir';
@@ -89,6 +89,10 @@ async function getLandoConfig(): Promise< LandoConfig > {
 		home: fakeHomeDir,
 		domain: 'vipdev.lndo.site',
 		version: 'unknown',
+		env: {
+			LANDO_HOST_USER_ID: process.platform === 'win32' ? '1000' : `${ userInfo().uid }`,
+			LANDO_HOST_GROUP_ID: process.platform === 'win32' ? '1000' : `${ userInfo().gid }`,
+		},
 	};
 
 	return buildConfig( config );