diff --git a/src/__tests__/helpers/utils.js b/src/__tests__/helpers/utils.js
index 9d5e7c59c..69946df96 100644
--- a/src/__tests__/helpers/utils.js
+++ b/src/__tests__/helpers/utils.js
@@ -74,6 +74,17 @@ function setupListbox() {
   document.body.append(wrapper)
   const listbox = wrapper.querySelector('[role="listbox"]')
   const options = Array.from(wrapper.querySelectorAll('[role="option"]'))
+
+  // the user is responsible for handling aria-selected on listbox options
+  options.forEach(el =>
+    el.addEventListener('click', e =>
+      e.target.setAttribute(
+        'aria-selected',
+        JSON.stringify(!JSON.parse(e.target.getAttribute('aria-selected'))),
+      ),
+    ),
+  )
+
   return {
     ...addListeners(listbox),
     listbox,
diff --git a/src/__tests__/select-options.js b/src/__tests__/select-options.js
index 24259ba0f..9be6ef22b 100644
--- a/src/__tests__/select-options.js
+++ b/src/__tests__/select-options.js
@@ -1,5 +1,5 @@
 import userEvent from '../'
-import {setupSelect, addListeners, setupListbox} from './helpers/utils'
+import {setupSelect, addListeners, setupListbox, setup} from './helpers/utils'
 
 test('fires correct events', () => {
   const {select, options, getEventSnapshot} = setupSelect()
@@ -22,6 +22,13 @@ test('fires correct events', () => {
     select[name="select"][value="1"] - click: Left (0)
     select[name="select"][value="2"] - input
     select[name="select"][value="2"] - change
+    select[name="select"][value="2"] - pointerover
+    select[name="select"][value="2"] - pointerenter
+    select[name="select"][value="2"] - mouseover: Left (0)
+    select[name="select"][value="2"] - mouseenter: Left (0)
+    select[name="select"][value="2"] - pointerup
+    select[name="select"][value="2"] - mouseup: Left (0)
+    select[name="select"][value="2"] - click: Left (0)
   `)
   const [o1, o2, o3] = options
   expect(o1.selected).toBe(false)
@@ -35,33 +42,22 @@ test('fires correct events on listBox select', () => {
   expect(getEventSnapshot()).toMatchInlineSnapshot(`
     Events fired on: ul[value="2"]
 
-    ul - pointerover
+    li#2[value="2"][aria-selected=false] - pointerover
     ul - pointerenter
-    ul - mouseover: Left (0)
+    li#2[value="2"][aria-selected=false] - mouseover: Left (0)
     ul - mouseenter: Left (0)
-    ul - pointermove
-    ul - mousemove: Left (0)
-    ul - pointerdown
-    ul - mousedown: Left (0)
-    ul - pointerup
-    ul - mouseup: Left (0)
-    ul - click: Left (0)
-    li#2[value="2"][aria-selected=true] - pointerover
-    ul[value="2"] - pointerenter
-    li#2[value="2"][aria-selected=true] - mouseover: Left (0)
-    ul[value="2"] - mouseenter: Left (0)
-    li#2[value="2"][aria-selected=true] - pointermove
-    li#2[value="2"][aria-selected=true] - mousemove: Left (0)
-    li#2[value="2"][aria-selected=true] - pointerover
-    ul[value="2"] - pointerenter
-    li#2[value="2"][aria-selected=true] - mouseover: Left (0)
-    ul[value="2"] - mouseenter: Left (0)
-    li#2[value="2"][aria-selected=true] - pointermove
-    li#2[value="2"][aria-selected=true] - mousemove: Left (0)
-    li#2[value="2"][aria-selected=true] - pointerdown
-    li#2[value="2"][aria-selected=true] - mousedown: Left (0)
-    li#2[value="2"][aria-selected=true] - pointerup
-    li#2[value="2"][aria-selected=true] - mouseup: Left (0)
+    li#2[value="2"][aria-selected=false] - pointermove
+    li#2[value="2"][aria-selected=false] - mousemove: Left (0)
+    li#2[value="2"][aria-selected=false] - pointerover
+    ul - pointerenter
+    li#2[value="2"][aria-selected=false] - mouseover: Left (0)
+    ul - mouseenter: Left (0)
+    li#2[value="2"][aria-selected=false] - pointermove
+    li#2[value="2"][aria-selected=false] - mousemove: Left (0)
+    li#2[value="2"][aria-selected=false] - pointerdown
+    li#2[value="2"][aria-selected=false] - mousedown: Left (0)
+    li#2[value="2"][aria-selected=false] - pointerup
+    li#2[value="2"][aria-selected=false] - mouseup: Left (0)
     li#2[value="2"][aria-selected=true] - click: Left (0)
     li#2[value="2"][aria-selected=true] - pointermove
     li#2[value="2"][aria-selected=true] - mousemove: Left (0)
@@ -150,6 +146,13 @@ test('a previously focused input gets blurred', () => {
   `)
 })
 
+test('throws an error if elements is neither select nor listbox', () => {
+  const {element} = setup(`<ul><li role='option'>foo</li></ul>`)
+  expect(() => userEvent.selectOptions(element, ['foo'])).toThrowError(
+    /neither select nor listbox/i,
+  )
+})
+
 test('throws an error one selected option does not match', () => {
   const {select} = setupSelect({multiple: true})
   expect(() =>
diff --git a/src/__tests__/utils.js b/src/__tests__/utils.js
new file mode 100644
index 000000000..bdd0d0e8b
--- /dev/null
+++ b/src/__tests__/utils.js
@@ -0,0 +1,73 @@
+import {isInstanceOfElement} from '../utils'
+import {setup} from './helpers/utils'
+
+// isInstanceOfElement can be removed once the peerDependency for @testing-library/dom is bumped to a version that includes https://github.com/testing-library/dom-testing-library/pull/885
+describe('check element type per isInstanceOfElement', () => {
+  let defaultViewDescriptor, spanDescriptor
+  beforeAll(() => {
+    defaultViewDescriptor = Object.getOwnPropertyDescriptor(
+      Object.getPrototypeOf(global.document),
+      'defaultView',
+    )
+    spanDescriptor = Object.getOwnPropertyDescriptor(
+      global.window,
+      'HTMLSpanElement',
+    )
+  })
+  afterEach(() => {
+    Object.defineProperty(
+      Object.getPrototypeOf(global.document),
+      'defaultView',
+      defaultViewDescriptor,
+    )
+    Object.defineProperty(global.window, 'HTMLSpanElement', spanDescriptor)
+  })
+
+  test('check in regular jest environment', () => {
+    const {element} = setup(`<span></span>`)
+
+    expect(element.ownerDocument.defaultView).toEqual(
+      expect.objectContaining({
+        HTMLSpanElement: expect.any(Function),
+      }),
+    )
+
+    expect(isInstanceOfElement(element, 'HTMLSpanElement')).toBe(true)
+    expect(isInstanceOfElement(element, 'HTMLDivElement')).toBe(false)
+  })
+
+  test('check in detached document', () => {
+    const {element} = setup(`<span></span>`)
+
+    Object.defineProperty(
+      Object.getPrototypeOf(element.ownerDocument),
+      'defaultView',
+      {value: null},
+    )
+
+    expect(element.ownerDocument.defaultView).toBe(null)
+
+    expect(isInstanceOfElement(element, 'HTMLSpanElement')).toBe(true)
+    expect(isInstanceOfElement(element, 'HTMLDivElement')).toBe(false)
+  })
+
+  test('check in environment not providing constructors on window', () => {
+    const {element} = setup(`<span></span>`)
+
+    delete global.window.HTMLSpanElement
+
+    expect(element.ownerDocument.defaultView.HTMLSpanElement).toBe(undefined)
+
+    expect(isInstanceOfElement(element, 'HTMLSpanElement')).toBe(true)
+    expect(isInstanceOfElement(element, 'HTMLDivElement')).toBe(false)
+  })
+
+  test('throw error if element is not created by HTML*Element constructor', () => {
+    const doc = new Document()
+
+    // constructor is global.Element
+    const element = doc.createElement('span')
+
+    expect(() => isInstanceOfElement(element, 'HTMLSpanElement')).toThrow()
+  })
+})
diff --git a/src/select-options.js b/src/select-options.js
index 967a34b34..9620814e7 100644
--- a/src/select-options.js
+++ b/src/select-options.js
@@ -1,4 +1,5 @@
 import {createEvent, getConfig, fireEvent} from '@testing-library/dom'
+import {isInstanceOfElement} from './utils'
 import {click} from './click'
 import {focus} from './focus'
 import {hover, unhover} from './hover'
@@ -36,53 +37,70 @@ function selectOptionsBase(newValue, select, values, init) {
 
   if (select.disabled || !selectedOptions.length) return
 
-  if (select.multiple) {
-    for (const option of selectedOptions) {
-      // events fired for multiple select are weird. Can't use hover...
-      fireEvent.pointerOver(option, init)
+  if (isInstanceOfElement(select, 'HTMLSelectElement')) {
+    if (select.multiple) {
+      for (const option of selectedOptions) {
+        // events fired for multiple select are weird. Can't use hover...
+        fireEvent.pointerOver(option, init)
+        fireEvent.pointerEnter(select, init)
+        fireEvent.mouseOver(option)
+        fireEvent.mouseEnter(select)
+        fireEvent.pointerMove(option, init)
+        fireEvent.mouseMove(option, init)
+        fireEvent.pointerDown(option, init)
+        fireEvent.mouseDown(option, init)
+        focus(select, init)
+        fireEvent.pointerUp(option, init)
+        fireEvent.mouseUp(option, init)
+        selectOption(option)
+        fireEvent.click(option, init)
+      }
+    } else if (selectedOptions.length === 1) {
+      // the click to open the select options
+      click(select, init)
+
+      selectOption(selectedOptions[0])
+
+      // the browser triggers another click event on the select for the click on the option
+      // this second click has no 'down' phase
+      fireEvent.pointerOver(select, init)
       fireEvent.pointerEnter(select, init)
-      fireEvent.mouseOver(option)
+      fireEvent.mouseOver(select)
       fireEvent.mouseEnter(select)
-      fireEvent.pointerMove(option, init)
-      fireEvent.mouseMove(option, init)
-      fireEvent.pointerDown(option, init)
-      fireEvent.mouseDown(option, init)
-      focus(select, init)
-      fireEvent.pointerUp(option, init)
-      fireEvent.mouseUp(option, init)
-      selectOption(option)
-      fireEvent.click(option, init)
+      fireEvent.pointerUp(select, init)
+      fireEvent.mouseUp(select, init)
+      fireEvent.click(select, init)
+    } else {
+      throw getConfig().getElementError(
+        `Cannot select multiple options on a non-multiple select`,
+        select,
+      )
     }
-  } else if (selectedOptions.length === 1) {
-    click(select, init)
-    selectOption(selectedOptions[0])
+  } else if (select.getAttribute('role') === 'listbox') {
+    selectedOptions.forEach(option => {
+      hover(option, init)
+      click(option, init)
+      unhover(option, init)
+    })
   } else {
     throw getConfig().getElementError(
-      `Cannot select multiple options on a non-multiple select`,
+      `Cannot select options on elements that are neither select nor listbox elements`,
       select,
     )
   }
 
   function selectOption(option) {
-    if (option.getAttribute('role') === 'option') {
-      option?.setAttribute?.('aria-selected', newValue)
-
-      hover(option, init)
-      click(option, init)
-      unhover(option, init)
-    } else {
-      option.selected = newValue
-      fireEvent(
-        select,
-        createEvent('input', select, {
-          bubbles: true,
-          cancelable: false,
-          composed: true,
-          ...init,
-        }),
-      )
-      fireEvent.change(select, init)
-    }
+    option.selected = newValue
+    fireEvent(
+      select,
+      createEvent('input', select, {
+        bubbles: true,
+        cancelable: false,
+        composed: true,
+        ...init,
+      }),
+    )
+    fireEvent.change(select, init)
   }
 }
 
diff --git a/src/upload.js b/src/upload.js
index 87bd447f5..a252b438b 100644
--- a/src/upload.js
+++ b/src/upload.js
@@ -6,16 +6,14 @@ import {focus} from './focus'
 function upload(element, fileOrFiles, init) {
   if (element.disabled) return
 
-  let files
-  let input = element
-
   click(element, init)
-  if (element.tagName === 'LABEL') {
-    files = element.control.multiple ? fileOrFiles : [fileOrFiles]
-    input = element.control
-  } else {
-    files = element.multiple ? fileOrFiles : [fileOrFiles]
-  }
+
+  const input = element.tagName === 'LABEL' ? element.control : element
+
+  const files = (Array.isArray(fileOrFiles)
+    ? fileOrFiles
+    : [fileOrFiles]
+  ).slice(0, input.multiple ? undefined : 1)
 
   // blur fires when the file selector pops up
   blur(element, init)
diff --git a/src/utils.js b/src/utils.js
index 8c284082b..fc46985a7 100644
--- a/src/utils.js
+++ b/src/utils.js
@@ -1,4 +1,36 @@
 import {getConfig} from '@testing-library/dom'
+import {getWindowFromNode} from '@testing-library/dom/dist/helpers'
+
+// isInstanceOfElement can be removed once the peerDependency for @testing-library/dom is bumped to a version that includes https://github.com/testing-library/dom-testing-library/pull/885
+/**
+ * Check if an element is of a given type.
+ *
+ * @param Element The element to test
+ * @param string Constructor name. E.g. 'HTMLSelectElement'
+ */
+function isInstanceOfElement(element, elementType) {
+  try {
+    const window = getWindowFromNode(element)
+    // Window usually has the element constructors as properties but is not required to do so per specs
+    if (typeof window[elementType] === 'function') {
+      return element instanceof window[elementType]
+    }
+  } catch (e) {
+    // The document might not be associated with a window
+  }
+
+  // Fall back to the constructor name as workaround for test environments that
+  // a) not associate the document with a window
+  // b) not provide the constructor as property of window
+  if (/^HTML(\w+)Element$/.test(element.constructor.name)) {
+    return element.constructor.name === elementType
+  }
+
+  // The user passed some node that is not created in a browser-like environment
+  throw new Error(
+    `Unable to verify if element is instance of ${elementType}. Please file an issue describing your test environment: https://github.com/testing-library/dom-testing-library/issues/new`,
+  )
+}
 
 function isMousePressEvent(event) {
   return (
@@ -257,7 +289,7 @@ function isClickable(element) {
   return (
     element.tagName === 'BUTTON' ||
     (element.tagName === 'A' && element.href) ||
-    (element instanceof element.ownerDocument.defaultView.HTMLInputElement &&
+    (isInstanceOfElement(element, 'HTMLInputElement') &&
       CLICKABLE_INPUT_TYPES.includes(element.type))
   )
 }
@@ -335,4 +367,5 @@ export {
   getValue,
   getSelectionRange,
   isContentEditable,
+  isInstanceOfElement,
 }