diff --git a/packages/core/upload/server/services/__tests__/upload.test.js b/packages/core/upload/server/services/__tests__/upload/formatFileInfo.test.js
similarity index 98%
rename from packages/core/upload/server/services/__tests__/upload.test.js
rename to packages/core/upload/server/services/__tests__/upload/formatFileInfo.test.js
index 0ebab147b5..884ae3bbf7 100644
--- a/packages/core/upload/server/services/__tests__/upload.test.js
+++ b/packages/core/upload/server/services/__tests__/upload/formatFileInfo.test.js
@@ -1,6 +1,6 @@
 'use strict';
 
-const uploadService = require('../upload')({});
+const uploadService = require('../../upload')({});
 
 describe('Upload service', () => {
   beforeAll(() => {
diff --git a/packages/core/upload/server/services/__tests__/upload/image.png b/packages/core/upload/server/services/__tests__/upload/image.png
new file mode 100644
index 0000000000..3ec3f1189a
Binary files /dev/null and b/packages/core/upload/server/services/__tests__/upload/image.png differ
diff --git a/packages/core/upload/server/services/__tests__/upload/uploadImage.test.js b/packages/core/upload/server/services/__tests__/upload/uploadImage.test.js
new file mode 100644
index 0000000000..b0317919f8
--- /dev/null
+++ b/packages/core/upload/server/services/__tests__/upload/uploadImage.test.js
@@ -0,0 +1,88 @@
+'use strict';
+
+const path = require('path');
+const fs = require('fs');
+const fse = require('fs-extra');
+const _ = require('lodash');
+const uploadService = require('../../upload')({});
+
+const testFilePath = path.join(__dirname, './image.png');
+const tmpWorkingDirectory = path.join(__dirname, './tmp');
+
+function mockUploadProvider(uploadFunc, props) {
+  const { responsiveDimensions = false } = props || {};
+
+  const default_config = {
+    plugin: {
+      upload: {
+        breakpoints: {
+          large: 1000,
+          medium: 750,
+        },
+      },
+    },
+  };
+
+  global.strapi = {
+    config: {
+      get: (path, defaultValue) => _.get(default_config, path, defaultValue),
+    },
+    plugins: {
+      upload: {
+        services: {
+          provider: {
+            upload: uploadFunc,
+          },
+          upload: {
+            getSettings: () => ({ responsiveDimensions }),
+          },
+          'image-manipulation': require('../../image-manipulation')(),
+        },
+      },
+    },
+  };
+}
+
+const getFileData = () => ({
+  alternativeText: 'image.png',
+  caption: 'image.png',
+  ext: '.png',
+  folder: null,
+  folderPath: '/',
+  getStream: () => fs.createReadStream(testFilePath),
+  hash: 'image_d9b4f84424',
+  height: 1000,
+  size: 4,
+  width: 1500,
+  tmpWorkingDirectory,
+});
+
+describe('Upload image', () => {
+  beforeAll(async () => {
+    // Create tmp directory if it does not exist
+    await fse.mkdir(tmpWorkingDirectory);
+  });
+
+  afterAll(async () => {
+    // Remove tmp directory
+    await fse.remove(tmpWorkingDirectory);
+  });
+  test('Upload with thubmnail', async () => {
+    let fileData = getFileData();
+    const upload = jest.fn();
+    mockUploadProvider(upload);
+
+    await uploadService.uploadImage(fileData);
+    expect(upload).toHaveBeenCalledTimes(2);
+  });
+
+  test('Upload with responsive formats', async () => {
+    let fileData = getFileData();
+    const upload = jest.fn();
+    mockUploadProvider(upload, { responsiveDimensions: true });
+
+    await uploadService.uploadImage(fileData);
+    // 1 for the original image, 1 for thubnhail, 2 for the responsive formats
+    expect(upload).toHaveBeenCalledTimes(4);
+  });
+});
diff --git a/packages/core/upload/server/services/upload.js b/packages/core/upload/server/services/upload.js
index 469cee1ef1..7c4b3b858c 100644
--- a/packages/core/upload/server/services/upload.js
+++ b/packages/core/upload/server/services/upload.js
@@ -176,6 +176,8 @@ module.exports = ({ strapi }) => ({
     // Store width and height of the original image
     const { width, height } = await getDimensions(fileData);
 
+    // Make sure this is assigned before calling upload
+    // That way it can mutate the width and height
     _.assign(fileData, {
       width,
       height,