diff --git a/cypress/dockerNode.ts b/cypress/dockerNode.ts
index e73ee2ffb..8f000daca 100644
--- a/cypress/dockerNode.ts
+++ b/cypress/dockerNode.ts
@@ -134,6 +134,7 @@ export const configureNextcloud = async function(branch = 'master') {
 	// Enable the app and give status
 	await runExec(container, ['php', 'occ', 'app:enable', '--force', 'viewer'], true)
 	await runExec(container, ['php', 'occ', 'app:enable', 'groupfolders', '--force'], true)
+	await runExec(container, ['php', 'occ', 'app:enable', 'files_trashbin', '--force'], true)
 	// await runExec(container, ['php', 'occ', 'app:list'], true)
 
 	console.log('└─ Nextcloud is now ready to use 🎉')
diff --git a/cypress/e2e/groupfolders.cy.ts b/cypress/e2e/groupfolders.cy.ts
index 92064e04b..1fed11450 100644
--- a/cypress/e2e/groupfolders.cy.ts
+++ b/cypress/e2e/groupfolders.cy.ts
@@ -20,10 +20,22 @@
  *
  */
 import {
+	addACLManagerUser,
 	addUserToGroup,
 	createGroup,
 	createGroupFolder,
 	deleteGroupFolder,
+	deleteFile,
+	enableACLPermissions,
+	enterFolder,
+	enterFolderInTrashbin,
+	fileOrFolderExists,
+	fileOrFolderDoesNotExist,
+	fileOrFolderExistsInTrashbin,
+	fileOrFolderDoesNotExistInTrashbin,
+	restoreFile,
+	setACLPermissions,
+	PERMISSION_DELETE,
 	PERMISSION_READ,
 	PERMISSION_WRITE,
 } from './groupfoldersUtils'
@@ -32,40 +44,220 @@ import { randHash } from '../utils'
 
 import type { User } from '@nextcloud/cypress'
 
-describe('Manage groupfolders', () => {
-	let user: User
+describe('Groupfolders ACLs and trashbin behavior', () => {
+	let user1: User
+	let user2: User
+	let managerUser: User
 	let groupFolderId: string
 	let groupName: string
 	let groupFolderName: string
 
-	before(() => {
+	beforeEach(() => {
+		if (groupFolderId) {
+			deleteGroupFolder(groupFolderId)
+		}
 		groupName = `test_group_${randHash()}`
 		groupFolderName = `test_group_folder_${randHash()}`
 
 		cy.createRandomUser()
 			.then(_user => {
-				user = _user
-				cy.login(user)
+				user1 = _user
+			})
+		cy.createRandomUser()
+			.then(_user => {
+				user2 = _user
+			})
+		cy.createRandomUser()
+			.then(_user => {
+				managerUser = _user
 
 				createGroup(groupName)
 					.then(() => {
-						addUserToGroup(groupName, user.userId)
-						createGroupFolder(groupFolderName, groupName, [PERMISSION_READ, PERMISSION_WRITE])
+						addUserToGroup(groupName, user1.userId)
+						addUserToGroup(groupName, user2.userId)
+						addUserToGroup(groupName, managerUser.userId)
+						createGroupFolder(groupFolderName, groupName, [PERMISSION_READ, PERMISSION_WRITE, PERMISSION_DELETE])
 							.then(_groupFolderId => {
 								groupFolderId = _groupFolderId
-								cy.visit('/apps/files')
+								enableACLPermissions(groupFolderId)
+								addACLManagerUser(groupFolderId,managerUser.userId)
 							})
 					})
 			})
 	})
 
-	after(() => {
-		if (groupFolderId) {
-			deleteGroupFolder(groupFolderId)
-		}
+	it('ACL, delete and restore', () => {
+		// Create two subfolders and two files as manager
+		cy.login(managerUser)
+		cy.mkdir(managerUser, `/${groupFolderName}/subfolder1`)
+		cy.mkdir(managerUser, `/${groupFolderName}/subfolder1/subfolder2`)
+		cy.uploadContent(managerUser, new Blob(['Content of the file']), 'text/plain', `/${groupFolderName}/subfolder1/file1.txt`)
+		cy.uploadContent(managerUser, new Blob(['Content of the file']), 'text/plain', `/${groupFolderName}/subfolder1/subfolder2/file2.txt`)
+
+		// Set ACL permissions
+		setACLPermissions(groupFolderId, '/subfolder1', [`+${PERMISSION_READ}`,`-${PERMISSION_WRITE}`], undefined, user1.userId)
+		setACLPermissions(groupFolderId, '/subfolder1', [`-${PERMISSION_READ}`], undefined, user2.userId)
+
+		// User1 has access
+		cy.login(user1)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		fileOrFolderExists('file1.txt')
+		enterFolder('subfolder2')
+		fileOrFolderExists('file2.txt')
+
+		// User2 has no access
+		cy.login(user2)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		fileOrFolderDoesNotExist('subfolder1')
+
+		// Delete files
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		deleteFile('file1.txt')
+		deleteFile('subfolder2')
+
+		// User1 sees it in trash
+		cy.login(user1)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderExistsInTrashbin('file1.txt')
+		enterFolderInTrashbin('subfolder2')
+		fileOrFolderExists('file2.txt')
+
+		// User2 does not
+		cy.login(user2)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderDoesNotExistInTrashbin('file1.txt')
+		fileOrFolderDoesNotExistInTrashbin('subfolder2')
+
+		// Restore files
+		cy.login(managerUser)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderExistsInTrashbin('file1.txt')
+		fileOrFolderExistsInTrashbin('subfolder2')
+		restoreFile('file1.txt')
+		restoreFile('subfolder2')
+
+		// User1 has access
+		cy.login(user1)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		fileOrFolderExists('subfolder1')
+		enterFolder('subfolder1')
+		fileOrFolderExists('file1.txt')
+		enterFolder('subfolder2')
+		fileOrFolderExists('file2.txt')
+
+		// User2 has no access
+		cy.login(user2)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		fileOrFolderDoesNotExist('subfolder1')
+	})
+
+	it.skip('ACL directly on deleted folder', () => {
+		// Create a subfolders and a file as manager
+		cy.login(managerUser)
+		cy.mkdir(managerUser, `/${groupFolderName}/subfolder1`)
+		cy.uploadContent(managerUser, new Blob(['Content of the file']), 'text/plain', `/${groupFolderName}/subfolder1/file1.txt`)
+
+		// Set ACL permissions on subfolder
+		setACLPermissions(groupFolderId, '/subfolder1', [`+${PERMISSION_READ}`,`-${PERMISSION_WRITE}`], undefined, user1.userId)
+		setACLPermissions(groupFolderId, '/subfolder1', [`-${PERMISSION_READ}`], undefined, user2.userId)
+
+		// Delete subfolder
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		deleteFile('subfolder1')
+
+		// User1 sees it in trash
+		cy.login(user1)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderExistsInTrashbin('subfolder1')
+		enterFolderInTrashbin('subfolder1')
+		fileOrFolderExists('file1.txt')
+
+		// User2 does not
+		cy.login(user2)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderDoesNotExistInTrashbin('subfolder1')
 	})
 
-	it('Visite the group folder', () => {
-		return true
+	it.skip('Delete, rename parent and restore', () => {
+		// Create a subfolders and a file as manager
+		cy.login(managerUser)
+		cy.mkdir(managerUser, `/${groupFolderName}/subfolder1`)
+		cy.uploadContent(managerUser, new Blob(['Content of the file']), 'text/plain', `/${groupFolderName}/subfolder1/file1.txt`)
+
+		// Delete file
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		deleteFile('file1.txt')
+
+		// Rename subfolder1
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="subfolder1"] [data-cy-files-list-row-actions]`).click()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="rename"]`).scrollIntoView()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="rename"]`).click()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="subfolder1"] [class="files-list__row-rename"] [class="input-field__input"]`).type('subfolder1renamed{enter}')
+		fileOrFolderExists('subfolder1renamed')
+
+		// Restore from trash
+		cy.visit('/apps/files/trashbin')
+		restoreFile('file1.txt')
+
+		// File should be restored in renamed folder
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		fileOrFolderExists('subfolder1renamed')
+		fileOrFolderDoesNotExist('file1.txt')
+		enterFolder('subfolder1renamed')
+		fileOrFolderExists('file1.txt')
+	})
+
+	it.skip('Delete, rename parent and check ACL', () => {
+		// Create a subfolders and a file as manager
+		cy.login(managerUser)
+		cy.mkdir(managerUser, `/${groupFolderName}/subfolder1`)
+		cy.uploadContent(managerUser, new Blob(['Content of the file']), 'text/plain', `/${groupFolderName}/subfolder1/file1.txt`)
+
+		// Set ACL permissions
+		setACLPermissions(groupFolderId, '/subfolder1', [`+${PERMISSION_READ}`,`-${PERMISSION_WRITE}`], undefined, user1.userId)
+		setACLPermissions(groupFolderId, '/subfolder1', [`-${PERMISSION_READ}`], undefined, user2.userId)
+
+		// Delete file
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		deleteFile('file1.txt')
+
+		// Rename subfolder1
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="subfolder1"] [data-cy-files-list-row-actions]`).click()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="rename"]`).scrollIntoView()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="rename"]`).click()
+		cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="subfolder1"] [class="files-list__row-rename"] [class="input-field__input"]`).type('subfolder1renamed{enter}')
+		fileOrFolderExists('subfolder1renamed')
+
+		// User1 sees it in trash
+		cy.login(user1)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderExistsInTrashbin('file1.txt')
+
+		// User2 does not
+		cy.login(user2)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderDoesNotExistInTrashbin('file1.txt')
 	})
 })
diff --git a/cypress/e2e/groupfoldersUtils.ts b/cypress/e2e/groupfoldersUtils.ts
index bc83a9c91..42cf61295 100644
--- a/cypress/e2e/groupfoldersUtils.ts
+++ b/cypress/e2e/groupfoldersUtils.ts
@@ -51,8 +51,8 @@ export function disableACLPermissions(groupFolderId: string) {
 	return cy.runOccCommand(`groupfolders:permissions ${groupFolderId} --disable`)
 }
 
-export function addACLManager(groupFolderId: string, groupOrUserName: string) {
-	return cy.runOccCommand(`groupfolders:permissions ${groupFolderId} --manage-add ${groupOrUserName}`)
+export function addACLManagerUser(groupFolderId: string, userName: string) {
+	return cy.runOccCommand(`groupfolders:permissions ${groupFolderId} --manage-add --user ${userName}`)
 }
 
 export function removeACLManager(groupFolderId: string, groupOrUserName: string) {
@@ -67,9 +67,47 @@ export function setACLPermissions(
 	userId?: string,
 ) {
 	const target = groupId !== undefined ? `--group ${groupId}` : `--user ${userId}`
-	return cy.runOccCommand(`groupfolders:permissions ${groupFolderId} ${path} ${aclPermissions} ${target}`)
+	return cy.runOccCommand(`groupfolders:permissions ${groupFolderId} ${path} ${target} -- ${aclPermissions.join(' ')}`)
 }
 
 export function deleteGroupFolder(groupFolderId: string) {
 	return cy.runOccCommand(`groupfolders:delete ${groupFolderId}`)
 }
+
+export function fileOrFolderExists(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="${name}"]`).should('be.visible')
+}
+
+export function fileOrFolderDoesNotExist(name: string) {
+	// Make sure file list is loaded first
+	cy.get(`[data-cy-files-list-tfoot],[data-cy-files-content-empty]`).should('be.visible')
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="${name}"]`).should('not.exist')
+}
+
+export function fileOrFolderExistsInTrashbin(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"]`).should('be.visible')
+}
+
+export function fileOrFolderDoesNotExistInTrashbin(name: string) {
+	// Make sure file list is loaded first
+	cy.get(`[data-cy-files-list-tfoot],[data-cy-files-content-empty]`).should('be.visible')
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"]`).should('not.exist')
+}
+
+export function enterFolder(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="${name}"]`).click()
+}
+
+export function enterFolderInTrashbin(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"]`).click()
+}
+
+export function deleteFile(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name="${name}"] [data-cy-files-list-row-actions]`).click()
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).scrollIntoView()
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).click()
+}
+
+export function restoreFile(name: string) {
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"] [data-cy-files-list-row-action="restore"]`).click()
+}
diff --git a/cypress/support/commands.ts b/cypress/support/commands.ts
index 187def7bb..d17922be3 100644
--- a/cypress/support/commands.ts
+++ b/cypress/support/commands.ts
@@ -45,6 +45,12 @@ declare global {
 			 */
 			uploadContent(user: User, content: Blob, mimeType: string, target: string): Cypress.Chainable<void>,
 
+			/**
+			 * Create a new directory
+			 * **Warning**: Using this function will reset the previous session
+			 */
+			mkdir(user: User, target: string): Cypress.Chainable<void>,
+
 			/**
 			 * Run an occ command in the docker container.
 			 */
@@ -56,6 +62,30 @@ declare global {
 const url = (Cypress.config('baseUrl') || '').replace(/\/index.php\/?$/g, '')
 Cypress.env('baseUrl', url)
 
+
+Cypress.Commands.add('mkdir', (user: User, target: string) => {
+	// eslint-disable-next-line cypress/unsafe-to-chain-command
+	cy.clearCookies()
+		.then({timeout:8000}, async () => {
+			try {
+				const rootPath = `${Cypress.env('baseUrl')}/remote.php/dav/files/${encodeURIComponent(user.userId)}`
+				const filePath = target.split('/').map(encodeURIComponent).join('/')
+				const response = await axios({
+					url: `${rootPath}${filePath}`,
+					method: 'MKCOL',
+					auth: {
+						username: user.userId,
+						password: user.password,
+					},
+				})
+				cy.log(`Created directory ${target}`, response)
+			} catch (error) {
+				cy.log('error', error)
+				throw new Error('Unable to process fixture')
+			}
+		})
+})
+
 /**
  * cy.uploadedFile - uploads a file from the fixtures folder
  * TODO: standardise in @nextcloud/cypress
@@ -85,7 +115,7 @@ Cypress.Commands.add('uploadFile', (user, fixture = 'image.jpg', mimeType = 'ima
  */
 Cypress.Commands.add('uploadContent', (user, blob, mimeType, target) => {
 	cy.clearCookies()
-		.then(async () => {
+		.then({timeout:8000}, async () => {
 			const fileName = basename(target)
 
 			// Process paths