diff --git a/packages/strapi-generate-new/lib/after.js b/packages/strapi-generate-new/lib/after.js
index 92c081aa21..50257d1fc8 100644
--- a/packages/strapi-generate-new/lib/after.js
+++ b/packages/strapi-generate-new/lib/after.js
@@ -83,6 +83,7 @@ module.exports = (scope, cb) => {
         'cache-min': 999999999
       }, err => {
         if (err) {
+          trackSuccess('didNotInstallProjectDependencies', scope);
           console.log();
           console.log('⚠️ You should run `npm install` into your application before starting it.');
           console.log();
@@ -106,8 +107,10 @@ module.exports = (scope, cb) => {
       const data = shell.exec(`yarn --cwd ${scope.rootPath} add ${alphaDependencies} --production`, { silent: true });
 
       if (data.stderr && data.code !== 0) {
+        trackSuccess('didNotInstallProjectDependencies', scope);
         cb();
       }
+
       pluginsInstallation();
     }
   } else {
@@ -150,6 +153,7 @@ module.exports = (scope, cb) => {
           loader = ora(`Install plugin ${cyan(defaultPlugin.name)}.`).start();
           exec(`node ${strapiBin} install ${defaultPlugin.name} ${scope.developerMode && defaultPlugin.core ? '--dev' : ''}`, (err) => {
             if (err) {
+              trackSuccess('didNotInstallProjectPlugins', scope);
               loader.warn(`An error occurred during ${defaultPlugin.name} plugin installation.`);
               console.log(err);
               return resolve();
diff --git a/packages/strapi-generate-new/lib/success.js b/packages/strapi-generate-new/lib/success.js
index e3711bfea5..9b36afce6e 100644
--- a/packages/strapi-generate-new/lib/success.js
+++ b/packages/strapi-generate-new/lib/success.js
@@ -5,6 +5,7 @@
  */
 
 // Node.js core.
+const os = require('os');
 const request = require('request');
 const { machineIdSync } = require('node-machine-id');
 
@@ -16,7 +17,8 @@ module.exports = function trackSuccess(event, scope, error) {
       uuid: scope.uuid,
       deviceId: machineIdSync(),
       properties: {
-        error
+        error,
+        os: os.type()
       }
     })
     .on('error', () => {});