diff --git a/cypress/e2e/files/FileSystemAPIUtils.ts b/cypress/e2e/files/FileSystemAPIUtils.ts
new file mode 100644
index 00000000000..995aef2ced5
--- /dev/null
+++ b/cypress/e2e/files/FileSystemAPIUtils.ts
@@ -0,0 +1,59 @@
+import { basename } from 'node:path'
+
+class FileSystemEntry {
+
+	private _isFile: boolean
+	private _fullPath: string
+
+	constructor(isFile: boolean, fullPath: string) {
+		this._isFile = isFile
+		this._fullPath = fullPath
+	}
+
+	get isFile() {
+		return !!this._isFile
+	}
+
+	get isDirectory() {
+		return !this.isFile
+	}
+
+	get name() {
+		return basename(this._fullPath)
+	}
+
+}
+
+export class FileSystemFileEntry extends FileSystemEntry {
+
+	private _contents: string
+
+	constructor(fullPath: string, contents: string) {
+		super(true, fullPath)
+		this._contents = contents
+	}
+
+	file(success: (file: File) => void) {
+		success(new File([this._contents], this.name))
+	}
+
+}
+
+export class FileSystemDirectoryEntry extends FileSystemEntry {
+
+	private _entries: FileSystemEntry[]
+
+	constructor(fullPath: string, entries: FileSystemEntry[]) {
+		super(false, fullPath)
+		this._entries = entries || []
+	}
+
+	createReader() {
+		return {
+			readEntries: (success: (entries: FileSystemEntry[]) => void) => {
+				success(this._entries)
+			},
+		}
+	}
+
+}
diff --git a/cypress/e2e/files/drag-n-drop.cy.ts b/cypress/e2e/files/drag-n-drop.cy.ts
index 9ede2536f67..4474f5b634c 100644
--- a/cypress/e2e/files/drag-n-drop.cy.ts
+++ b/cypress/e2e/files/drag-n-drop.cy.ts
@@ -1,6 +1,6 @@
 import { getRowForFile } from './FilesUtils.ts'
 
-describe('files: Drag and Drop', { testIsolation: true }, () => {
+describe('files: Drag and Drop legacy', { testIsolation: true }, () => {
 	beforeEach(() => {
 		cy.createRandomUser().then((user) => {
 			cy.login(user)
@@ -14,7 +14,9 @@ describe('files: Drag and Drop', { testIsolation: true }, () => {
 
 		cy.intercept('PUT', /\/remote.php\/dav\/files\//).as('uploadFile')
 
+		// Make sure the drop notice is not visible
 		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+
 		// Trigger the drop notice
 		cy.get('main.app-content').trigger('dragover', { dataTransfer })
 		cy.get('[data-cy-files-drag-drop-area]').should('be.visible')
@@ -27,6 +29,11 @@ describe('files: Drag and Drop', { testIsolation: true }, () => {
 
 		cy.wait('@uploadFile')
 
+		// Make sure the upload is finished
+		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+		cy.get('[data-cy-upload-picker] progress').should('not.be.visible')
+		cy.get('@uploadFile.all').should('have.length', 1)
+
 		getRowForFile('single-file.txt').should('be.visible')
 		getRowForFile('single-file.txt').find('[data-cy-files-list-row-size]').should('contain', '6 KB')
 	})
@@ -38,6 +45,58 @@ describe('files: Drag and Drop', { testIsolation: true }, () => {
 
 		cy.intercept('PUT', /\/remote.php\/dav\/files\//).as('uploadFile')
 
+		// Make sure the drop notice is not visible
+		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+
+		// Trigger the drop notice
+		cy.get('main.app-content').trigger('dragover', { dataTransfer })
+		cy.get('[data-cy-files-drag-drop-area]').should('be.visible')
+
+		// Upload drop a file
+		cy.get('[data-cy-files-drag-drop-area]').selectFile([
+			{
+				fileName: 'first.txt',
+				contents: ['Hello'],
+			},
+			{
+				fileName: 'second.txt',
+				contents: ['World'],
+			},
+		], { action: 'drag-drop' })
+
+		cy.wait('@uploadFile')
+
+		// Make sure the upload is finished
+		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+		cy.get('[data-cy-upload-picker] progress').should('not.be.visible')
+		cy.get('@uploadFile.all').should('have.length', 2)
+
+		getRowForFile('first.txt').should('be.visible')
+		getRowForFile('second.txt').should('be.visible')
+	})
+
+	it('will ignore legacy Folders', () => {
+		cy.window().then((win) => {
+			// Remove the Filesystem API to force the legacy File API
+			// See how cypress mocks the Filesystem API in https://github.com/cypress-io/cypress/blob/74109094a92df3bef073dda15f17194f31850d7d/packages/driver/src/cy/commands/actions/selectFile.ts#L24-L37
+			Object.defineProperty(win.DataTransferItem.prototype, 'getAsEntry', { get: undefined })
+			Object.defineProperty(win.DataTransferItem.prototype, 'webkitGetAsEntry', { get: undefined })
+		})
+
+		const dataTransfer = new DataTransfer()
+		dataTransfer.items.add(new File([], 'first.txt'))
+		dataTransfer.items.add(new File([], 'second.txt'))
+
+		// Legacy File API (not FileSystem API), will treat Folders as Files
+		// with empty type and empty content
+		dataTransfer.items.add(new File([], 'Foo', { type: 'httpd/unix-directory' }))
+		dataTransfer.items.add(new File([], 'Bar'))
+
+		cy.intercept('PUT', /\/remote.php\/dav\/files\//).as('uploadFile')
+
+		// Make sure the drop notice is not visible
+		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+
 		// Trigger the drop notice
 		cy.get('main.app-content').trigger('dragover', { dataTransfer })
 		cy.get('[data-cy-files-drag-drop-area]').should('be.visible')
@@ -52,11 +111,26 @@ describe('files: Drag and Drop', { testIsolation: true }, () => {
 				fileName: 'second.txt',
 				contents: ['World'],
 			},
+			{
+				fileName: 'Foo',
+				contents: {},
+			},
+			{
+				fileName: 'Bar',
+				contents: { mimeType: 'httpd/unix-directory' },
+			},
 		], { action: 'drag-drop' })
 
 		cy.wait('@uploadFile')
 
+		// Make sure the upload is finished
+		cy.get('[data-cy-files-drag-drop-area]').should('not.be.visible')
+		cy.get('[data-cy-upload-picker] progress').should('not.be.visible')
+		cy.get('@uploadFile.all').should('have.length', 2)
+
 		getRowForFile('first.txt').should('be.visible')
 		getRowForFile('second.txt').should('be.visible')
+		getRowForFile('Foo').should('not.exist')
+		getRowForFile('Bar').should('not.exist')
 	})
 })