diff --git a/cypress/e2e/groupfolders.cy.ts b/cypress/e2e/groupfolders.cy.ts
index 4c5766b2b..6a160c030 100644
--- a/cypress/e2e/groupfolders.cy.ts
+++ b/cypress/e2e/groupfolders.cy.ts
@@ -26,7 +26,9 @@ import {
 	createGroupFolder,
 	deleteGroupFolder,
 	deleteFile,
+	deleteFileFromTrashbin,
 	deleteFolder,
+	deleteFolderFromTrashbin,
 	enableACLPermissions,
 	enterFolder,
 	enterFolderInTrashbin,
@@ -276,4 +278,42 @@ describe('Groupfolders ACLs and trashbin behavior', () => {
 		cy.visit('/apps/files/trashbin')
 		fileOrFolderDoesNotExistInTrashbin('file1.txt')
 	})
+
+	it('ACL, delete and delete from trash', () => {
+		// 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)
+
+		// Delete files
+		cy.log('Deleting the files')
+		cy.logout()
+		cy.login(managerUser)
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		deleteFile('file1.txt')
+		cy.visit('/apps/files')
+		enterFolder(groupFolderName)
+		enterFolder('subfolder1')
+		deleteFolder('subfolder2')
+
+		// Delete files from trash
+		cy.log('Deleting the files permanently')
+		cy.logout()
+		cy.login(managerUser)
+		cy.visit('/apps/files/trashbin')
+		fileOrFolderExistsInTrashbin('file1.txt')
+		deleteFileFromTrashbin('file1.txt')
+		fileOrFolderExistsInTrashbin('subfolder2')
+		deleteFolderFromTrashbin('subfolder2')
+		fileOrFolderDoesNotExistInTrashbin('file1.txt')
+		fileOrFolderDoesNotExistInTrashbin('subfolder2')
+	})
 })
diff --git a/cypress/e2e/groupfoldersUtils.ts b/cypress/e2e/groupfoldersUtils.ts
index 050536a9e..57a02b3b1 100644
--- a/cypress/e2e/groupfoldersUtils.ts
+++ b/cypress/e2e/groupfoldersUtils.ts
@@ -119,6 +119,15 @@ export function deleteFolder(name: string) {
 	cy.wait('@delete').its('response.statusCode').should('eq', 204)
 }
 
+export function deleteFolderFromTrashbin(name: string) {
+	cy.intercept({ times: 1, method: 'DELETE', url: `**/dav/trashbin/**/${name}.d*` }).as('delete')
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"] [data-cy-files-list-row-actions] button:not([data-cy-files-list-row-action])`).click()
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).should('be.visible')
+	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()
+	cy.wait('@delete').its('response.statusCode').should('eq', 204)
+}
+
 export function deleteFile(name: string) {
 	cy.intercept({ times: 1, method: 'DELETE', url: `**/dav/files/**/${name}` }).as('delete')
 	// For files wait for preview to load and release lock
@@ -135,6 +144,22 @@ export function deleteFile(name: string) {
 	cy.wait('@delete').its('response.statusCode').should('eq', 204)
 }
 
+export function deleteFileFromTrashbin(name: string) {
+	cy.intercept({ times: 1, method: 'DELETE', url: `**/dav/trashbin/**/${name}.d*` }).as('delete')
+	// For files wait for preview to load and release lock
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"] .files-list__row-icon img`)
+	.should('be.visible')
+	.and(($img) => {
+		// "naturalWidth" and "naturalHeight" are set when the image loads
+		expect($img[0].naturalWidth, 'image has natural width').to.be.greaterThan(0)
+	})
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"] [data-cy-files-list-row-actions] button:not([data-cy-files-list-row-action])`).click()
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).should('be.visible')
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).scrollIntoView()
+	cy.get(`[data-cy-files-list] [data-cy-files-list-row-action="delete"]`).click()
+	cy.wait('@delete').its('response.statusCode').should('eq', 204)
+}
+
 export function restoreFile(name: string) {
 	cy.get(`[data-cy-files-list] [data-cy-files-list-row-name^="${name}.d"] [data-cy-files-list-row-action="restore"]`).click()
 }