diff --git a/apps/admin-x-framework/src/api/images.ts b/apps/admin-x-framework/src/api/images.ts
index 93ddf1de8c..5c087dd3b7 100644
--- a/apps/admin-x-framework/src/api/images.ts
+++ b/apps/admin-x-framework/src/api/images.ts
@@ -7,13 +7,20 @@ export interface ImagesResponseType {
     }[];
 }
 
-export const useUploadImage = createMutation<ImagesResponseType, {file: File}>({
+// eslint-disable-next-line no-shadow
+export enum ImageStatus {
+    NEW = 'new',
+    EDITED = 'edited',
+}
+
+export const useUploadImage = createMutation<ImagesResponseType, {file: File, status?: ImageStatus}>({
     method: 'POST',
     path: () => '/images/upload/',
-    body: ({file}) => {
+    body: ({file, status = ImageStatus.NEW}) => {
         const formData = new FormData();
         formData.append('file', file);
         formData.append('purpose', 'image');
+        formData.append('status', status);
         return formData;
     }
 });
diff --git a/apps/admin-x-settings/src/components/settings/general/Facebook.tsx b/apps/admin-x-settings/src/components/settings/general/Facebook.tsx
index bd0dbee0ed..43ce587dc4 100644
--- a/apps/admin-x-settings/src/components/settings/general/Facebook.tsx
+++ b/apps/admin-x-settings/src/components/settings/general/Facebook.tsx
@@ -4,7 +4,7 @@ import usePinturaEditor from '../../../hooks/usePinturaEditor';
 import useSettingGroup from '../../../hooks/useSettingGroup';
 import {APIError} from '@tryghost/admin-x-framework/errors';
 import {FacebookLogo, ImageUpload, SettingGroupContent, TextField, withErrorBoundary} from '@tryghost/admin-x-design-system';
-import {getImageUrl, useUploadImage} from '@tryghost/admin-x-framework/api/images';
+import {getImageUrl, ImageStatus, useUploadImage} from '@tryghost/admin-x-framework/api/images';
 import {getSettingValues} from '@tryghost/admin-x-framework/api/settings';
 import {useHandleError} from '@tryghost/admin-x-framework/hooks';
 
@@ -86,7 +86,7 @@ const Facebook: React.FC<{ keywords: string[] }> = ({keywords}) => {
                                 openEditor: async () => editor.openEditor({
                                     image: facebookImage || '',
                                     handleSave: async (file:File) => {
-                                        const imageUrl = getImageUrl(await uploadImage({file}));
+                                        const imageUrl = getImageUrl(await uploadImage({file, status: ImageStatus.EDITED}));
                                         updateSetting('og_image', imageUrl);
                                     }
                                 })
diff --git a/apps/admin-x-settings/src/components/settings/general/Twitter.tsx b/apps/admin-x-settings/src/components/settings/general/Twitter.tsx
index be40650c32..f82e618612 100644
--- a/apps/admin-x-settings/src/components/settings/general/Twitter.tsx
+++ b/apps/admin-x-settings/src/components/settings/general/Twitter.tsx
@@ -4,7 +4,7 @@ import usePinturaEditor from '../../../hooks/usePinturaEditor';
 import useSettingGroup from '../../../hooks/useSettingGroup';
 import {APIError} from '@tryghost/admin-x-framework/errors';
 import {ImageUpload, SettingGroupContent, TextField, XLogo, withErrorBoundary} from '@tryghost/admin-x-design-system';
-import {getImageUrl, useUploadImage} from '@tryghost/admin-x-framework/api/images';
+import {getImageUrl, ImageStatus, useUploadImage} from '@tryghost/admin-x-framework/api/images';
 import {getSettingValues} from '@tryghost/admin-x-framework/api/settings';
 import {useHandleError} from '@tryghost/admin-x-framework/hooks';
 
@@ -82,7 +82,7 @@ const Twitter: React.FC<{ keywords: string[] }> = ({keywords}) => {
                                 openEditor: async () => editor.openEditor({
                                     image: twitterImage || '',
                                     handleSave: async (file:File) => {
-                                        const imageUrl = getImageUrl(await uploadImage({file}));
+                                        const imageUrl = getImageUrl(await uploadImage({file, status: ImageStatus.EDITED}));
                                         updateSetting('twitter_image', imageUrl);
                                     }
                                 })
diff --git a/apps/admin-x-settings/src/components/settings/general/UserDetailModal.tsx b/apps/admin-x-settings/src/components/settings/general/UserDetailModal.tsx
index 27e492db49..ad3d4cddb9 100644
--- a/apps/admin-x-settings/src/components/settings/general/UserDetailModal.tsx
+++ b/apps/admin-x-settings/src/components/settings/general/UserDetailModal.tsx
@@ -15,7 +15,7 @@ import {ErrorMessages, useForm, useHandleError} from '@tryghost/admin-x-framewor
 import {HostLimitError, useLimiter} from '../../../hooks/useLimiter';
 import {RoutingModalProps, useRouting} from '@tryghost/admin-x-framework/routing';
 import {User, canAccessSettings, hasAdminAccess, isAdminUser, isAuthorOrContributor, isEditorUser, isOwnerUser, useDeleteUser, useEditUser, useMakeOwner} from '@tryghost/admin-x-framework/api/users';
-import {getImageUrl, useUploadImage} from '@tryghost/admin-x-framework/api/images';
+import {getImageUrl, ImageStatus, useUploadImage} from '@tryghost/admin-x-framework/api/images';
 import {useGlobalData} from '../../providers/GlobalDataProvider';
 import {validateFacebookUrl, validateTwitterUrl} from '../../../utils/socialUrls';
 
@@ -246,9 +246,9 @@ const UserDetailModalContent: React.FC<{user: User}> = ({user}) => {
         });
     };
 
-    const handleImageUpload = async (image: string, file: File) => {
+    const handleImageUpload = async (image: string, file: File, status: ImageStatus = ImageStatus.NEW) => {
         try {
-            const imageUrl = getImageUrl(await uploadImage({file}));
+            const imageUrl = getImageUrl(await uploadImage({file, status}));
 
             switch (image) {
             case 'cover_image':
@@ -383,7 +383,7 @@ const UserDetailModalContent: React.FC<{user: User}> = ({user}) => {
                                             openEditor: async () => editor.openEditor({
                                                 image: formState.profile_image || '',
                                                 handleSave: async (file:File) => {
-                                                    handleImageUpload('profile_image', file);
+                                                    handleImageUpload('profile_image', file, ImageStatus.EDITED);
                                                 }
                                             })
                                         }
@@ -421,7 +421,7 @@ const UserDetailModalContent: React.FC<{user: User}> = ({user}) => {
                                         openEditor: async () => editor.openEditor({
                                             image: formState.cover_image || '',
                                             handleSave: async (file:File) => {
-                                                handleImageUpload('cover_image', file);
+                                                handleImageUpload('cover_image', file, ImageStatus.EDITED);
                                             }
                                         })
                                     }
diff --git a/apps/admin-x-settings/src/components/settings/site/designAndBranding/BrandSettings.tsx b/apps/admin-x-settings/src/components/settings/site/designAndBranding/BrandSettings.tsx
index 9b2346b7d6..c11bf33cc9 100644
--- a/apps/admin-x-settings/src/components/settings/site/designAndBranding/BrandSettings.tsx
+++ b/apps/admin-x-settings/src/components/settings/site/designAndBranding/BrandSettings.tsx
@@ -131,7 +131,7 @@ const BrandSettings: React.FC<{ values: BrandSettingValues, updateSetting: (key:
                                     image: values.coverImage || '',
                                     handleSave: async (file:File) => {
                                         try {
-                                            updateSetting('cover_image', getImageUrl(await uploadImage({file})));
+                                            updateSetting('cover_image', getImageUrl(await uploadImage({file, original: values.coverImage})));
                                         } catch (e) {
                                             handleError(e);
                                         }
diff --git a/ghost/admin/app/components/gh-image-uploader.js b/ghost/admin/app/components/gh-image-uploader.js
index 6da150ecfe..e2181bad41 100644
--- a/ghost/admin/app/components/gh-image-uploader.js
+++ b/ghost/admin/app/components/gh-image-uploader.js
@@ -15,13 +15,16 @@ import {isBlank} from '@ember/utils';
 import {run} from '@ember/runloop';
 import {inject as service} from '@ember/service';
 
+export const IMAGE_STATUS_NEW = 'new';
+export const IMAGE_STATUS_EDITED = 'edited';
+
 export const IMAGE_MIME_TYPES = 'image/gif,image/jpg,image/jpeg,image/png,image/svg+xml,image/webp';
 export const IMAGE_EXTENSIONS = ['gif', 'jpg', 'jpeg', 'png', 'svg', 'svgz', 'webp'];
-export const IMAGE_PARAMS = {purpose: 'image'};
+export const IMAGE_PARAMS = {purpose: 'image', status: IMAGE_STATUS_NEW};
 
 export const ICON_EXTENSIONS = ['gif', 'ico', 'jpg', 'jpeg', 'png', 'svg', 'svgz', 'webp'];
 export const ICON_MIME_TYPES = 'image/x-icon,image/vnd.microsoft.icon,image/gif,image/jpg,image/jpeg,image/png,image/svg+xml,image/webp';
-export const ICON_PARAMS = {purpose: 'icon'};
+export const ICON_PARAMS = {purpose: 'icon', status: IMAGE_STATUS_NEW};
 
 export default Component.extend({
     ajax: service(),
diff --git a/ghost/admin/app/components/gh-uploader.js b/ghost/admin/app/components/gh-uploader.js
index 1f22fb36a4..0c30027360 100644
--- a/ghost/admin/app/components/gh-uploader.js
+++ b/ghost/admin/app/components/gh-uploader.js
@@ -6,7 +6,9 @@ import {
     ICON_EXTENSIONS,
     ICON_MIME_TYPES,
     IMAGE_EXTENSIONS,
-    IMAGE_MIME_TYPES
+    IMAGE_MIME_TYPES,
+    IMAGE_STATUS_EDITED,
+    IMAGE_STATUS_NEW
 } from 'ghost-admin/components/gh-image-uploader';
 import {all, task} from 'ember-concurrency';
 import {isArray} from '@ember/array';
@@ -95,7 +97,7 @@ export default Component.extend({
         this._uploadTrackers = [];
 
         if (!this.paramsHash) {
-            this.set('paramsHash', {purpose: 'image'});
+            this.set('paramsHash', {purpose: 'image', status: IMAGE_STATUS_NEW});
         }
 
         this.set('imageExtensions', IMAGE_EXTENSIONS);
@@ -333,6 +335,10 @@ export default Component.extend({
             formData.append(key, this.paramsHash[key]);
         });
 
+        if (file.edited) {
+            formData.set('status', IMAGE_STATUS_EDITED);
+        }
+
         return formData;
     },
 
diff --git a/ghost/admin/app/components/koenig-image-editor.js b/ghost/admin/app/components/koenig-image-editor.js
index 1ab92083b2..40b80d3f23 100644
--- a/ghost/admin/app/components/koenig-image-editor.js
+++ b/ghost/admin/app/components/koenig-image-editor.js
@@ -230,6 +230,7 @@ export default class KoenigImageEditor extends Component {
 
             editor.on('process', (result) => {
                 // save edited image
+                result.dest.edited = true;
                 try {
                     if (this.args.saveImage) {
                         this.args.saveImage(result.dest);
diff --git a/ghost/admin/app/components/koenig-lexical-editor.js b/ghost/admin/app/components/koenig-lexical-editor.js
index 18e6d2df19..9e434e57c4 100644
--- a/ghost/admin/app/components/koenig-lexical-editor.js
+++ b/ghost/admin/app/components/koenig-lexical-editor.js
@@ -9,12 +9,16 @@ import {didCancel, task} from 'ember-concurrency';
 import {inject} from 'ghost-admin/decorators/inject';
 import {inject as service} from '@ember/service';
 
+const IMAGE_STATUS_NEW = 'new';
+const IMAGE_STATUS_EDITED = 'edited';
+
 export const fileTypes = {
     image: {
         mimeTypes: ['image/gif', 'image/jpg', 'image/jpeg', 'image/png', 'image/svg+xml', 'image/webp'],
         extensions: ['gif', 'jpg', 'jpeg', 'png', 'svg', 'svgz', 'webp'],
         endpoint: '/images/upload/',
-        resourceName: 'images'
+        resourceName: 'images',
+        uploadParams: {purpose: 'image', status: IMAGE_STATUS_NEW}
     },
     video: {
         mimeTypes: ['video/mp4', 'video/webm', 'video/ogg'],
@@ -537,10 +541,16 @@ export default class KoenigLexicalEditor extends Component {
                 const fileFormData = new FormData();
                 fileFormData.append('file', file, file.name);
 
+                formData = {...fileTypes[type].uploadParams, ...formData};
+
                 Object.keys(formData || {}).forEach((key) => {
                     fileFormData.append(key, formData[key]);
                 });
 
+                if (type === 'image' && file.edited) {
+                    fileFormData.set('status', IMAGE_STATUS_EDITED);
+                }
+
                 const url = `${ghostPaths().apiRoot}${fileTypes[type].endpoint}`;
 
                 try {
diff --git a/ghost/core/core/server/api/endpoints/images.js b/ghost/core/core/server/api/endpoints/images.js
index b95dedc0ab..4f6d4bac06 100644
--- a/ghost/core/core/server/api/endpoints/images.js
+++ b/ghost/core/core/server/api/endpoints/images.js
@@ -1,11 +1,14 @@
 /* eslint-disable ghost/ghost-custom/max-api-complexity */
 const path = require('path');
+const uuid = require('uuid');
 const errors = require('@tryghost/errors');
 const imageTransform = require('@tryghost/image-transform');
 
 const storage = require('../../adapters/storage');
 const config = require('../../../shared/config');
 
+const IMAGE_STATUS_EDITED = 'edited';
+
 /** @type {import('@tryghost/api-framework').Controller} */
 const controller = {
     docName: 'images',
@@ -24,6 +27,13 @@ const controller = {
             // Trim _o from file name (not allowed suffix)
             frame.file.name = frame.file.name.replace(/_o(\.\w+?)$/, '$1');
 
+            // If this an edited version of an existing image, anonymise the name
+            if (frame.data.status === IMAGE_STATUS_EDITED) {
+                const ext = path.extname(frame.file.name);
+
+                frame.file.name = `${uuid.v4()}${ext}`;
+            }
+
             // CASE: image transform is not capable of transforming file (e.g. .gif)
             if (imageTransform.shouldResizeFileExtension(frame.file.ext) && imageOptimizationOptions.resize) {
                 const out = `${frame.file.path}_processed`;
diff --git a/ghost/core/test/e2e-api/admin/images.test.js b/ghost/core/test/e2e-api/admin/images.test.js
index ee882b35cb..acd8ae1e43 100644
--- a/ghost/core/test/e2e-api/admin/images.test.js
+++ b/ghost/core/test/e2e-api/admin/images.test.js
@@ -14,6 +14,9 @@ const {imageSize} = require('../../../core/server/lib/image');
 const configUtils = require('../../utils/configUtils');
 const logging = require('@tryghost/logging');
 
+const IMAGE_STATUS_NEW = 'new';
+const IMAGE_STATUS_EDITED = 'edited';
+
 const images = [];
 let agent, frontendAgent, ghostServer;
 /**
@@ -23,9 +26,10 @@ let agent, frontendAgent, ghostServer;
  * @param {string} options.filename
  * @param {string} options.contentType
  * @param {string} [options.ref]
+ * @param {string} [options.status]
  * @returns
  */
-const uploadImageRequest = ({fileContents, filename, contentType, ref}) => {
+const uploadImageRequest = ({fileContents, filename, contentType, ref, status = IMAGE_STATUS_NEW}) => {
     const form = new FormData();
     form.append('file', fileContents, {
         filename,
@@ -33,6 +37,8 @@ const uploadImageRequest = ({fileContents, filename, contentType, ref}) => {
     });
 
     form.append('purpose', 'image');
+    form.append('status', status);
+
     if (ref) {
         form.append('ref', ref);
     }
@@ -400,4 +406,21 @@ describe('Images API', function () {
             });
         sinon.assert.calledOnce(loggingStub);
     });
+
+    it('Anonymizes the name of an edited image', async function () {
+        const originalFilePath = p.join(__dirname, '/../../utils/fixtures/images/ghost-logo.png');
+        const fileContents = await fs.readFile(originalFilePath);
+        const filename = 'foobarbaz.png';
+
+        const {body} = await uploadImageRequest({fileContents, filename, contentType: 'image/png', status: IMAGE_STATUS_EDITED})
+            .expectStatus(201);
+
+        const name = body.images[0].url.split('/').pop();
+
+        // Assert that name has been changed
+        assert.equal(name !== filename, true);
+
+        // Assert that name is a UUID v4
+        assert.match(name, /^[0-9a-f]{8}-[0-9a-f]{4}-4[0-9a-f]{3}-[89ab][0-9a-f]{3}-[0-9a-f]{12}\.png$/);
+    });
 });