diff --git a/packages/core/strapi/lib/services/metrics/index.js b/packages/core/strapi/lib/services/metrics/index.js
index 46094dfafb..04a8921754 100644
--- a/packages/core/strapi/lib/services/metrics/index.js
+++ b/packages/core/strapi/lib/services/metrics/index.js
@@ -17,6 +17,7 @@ const LIMITED_EVENTS = [
   'didSaveMediaWithCaption',
   'didDisableResponsiveDimensions',
   'didEnableResponsiveDimensions',
+  'didInitializePluginUpload',
 ];
 
 const createTelemetryInstance = (strapi) => {
diff --git a/packages/core/upload/server/bootstrap.js b/packages/core/upload/server/bootstrap.js
index a0db872e93..7cd2ccde56 100644
--- a/packages/core/upload/server/bootstrap.js
+++ b/packages/core/upload/server/bootstrap.js
@@ -37,7 +37,8 @@ module.exports = async ({ strapi }) => {
 
   await registerPermissionActions();
 
-  await getService('metrics').registerCron();
+  await getService('weeklyMetrics').registerCron();
+  await getService('metrics').sendUploadPluginMetrics();
 };
 
 const registerPermissionActions = async () => {
diff --git a/packages/core/upload/server/services/__tests__/metrics.js b/packages/core/upload/server/services/__tests__/metrics.js
index 956e86648d..4b267feca9 100644
--- a/packages/core/upload/server/services/__tests__/metrics.js
+++ b/packages/core/upload/server/services/__tests__/metrics.js
@@ -1,6 +1,6 @@
 'use strict';
 
-const metricsService = require('../metrics');
+const metricsService = require('../metrics/weekly-metrics');
 
 describe('metrics', () => {
   describe('computeMetrics', () => {
diff --git a/packages/core/upload/server/services/index.js b/packages/core/upload/server/services/index.js
index 09f2b148de..70813b8e3d 100644
--- a/packages/core/upload/server/services/index.js
+++ b/packages/core/upload/server/services/index.js
@@ -5,7 +5,8 @@ const upload = require('./upload');
 const imageManipulation = require('./image-manipulation');
 const folder = require('./folder');
 const file = require('./file');
-const metrics = require('./metrics');
+const weeklyMetrics = require('./metrics/weekly-metrics');
+const metrics = require('./metrics/metrics');
 const apiUploadFolder = require('./api-upload-folder');
 const extensions = require('./extensions');
 
@@ -14,6 +15,7 @@ module.exports = {
   upload,
   folder,
   file,
+  weeklyMetrics,
   metrics,
   'image-manipulation': imageManipulation,
   'api-upload-folder': apiUploadFolder,
diff --git a/packages/core/upload/server/services/metrics/metrics.js b/packages/core/upload/server/services/metrics/metrics.js
new file mode 100644
index 0000000000..aa431dcf5d
--- /dev/null
+++ b/packages/core/upload/server/services/metrics/metrics.js
@@ -0,0 +1,15 @@
+'use strict';
+
+const getProviderName = () => strapi.config.get('plugin.upload.provider', 'local');
+const getProviderIsPrivate = () => strapi.plugin('upload').provider.isPrivate();
+
+module.exports = ({ strapi }) => ({
+  async sendUploadPluginMetrics() {
+    const provider = await getProviderName();
+    const isPrivate = await getProviderIsPrivate();
+
+    await strapi.telemetry.send('didInitializePluginUpload', {
+      groupProperties: { provider, isPrivate },
+    });
+  },
+});
diff --git a/packages/core/upload/server/services/metrics.js b/packages/core/upload/server/services/metrics/weekly-metrics.js
similarity index 96%
rename from packages/core/upload/server/services/metrics.js
rename to packages/core/upload/server/services/metrics/weekly-metrics.js
index a0f4976871..a2074d3cc9 100644
--- a/packages/core/upload/server/services/metrics.js
+++ b/packages/core/upload/server/services/metrics/weekly-metrics.js
@@ -2,8 +2,8 @@
 
 const { defaultTo } = require('lodash/fp');
 const { add } = require('date-fns');
-const { FOLDER_MODEL_UID, FILE_MODEL_UID } = require('../constants');
-const { getWeeklyCronScheduleAt } = require('../utils/cron');
+const { FOLDER_MODEL_UID, FILE_MODEL_UID } = require('../../constants');
+const { getWeeklyCronScheduleAt } = require('../../utils/cron');
 
 const ONE_WEEK = 7 * 24 * 60 * 60 * 1000;