diff --git a/src/__tests__/upload.test.ts b/src/__tests__/upload.test.ts
new file mode 100644
index 0000000..26b1d4d
--- /dev/null
+++ b/src/__tests__/upload.test.ts
@@ -0,0 +1,114 @@
+import crypto from 'crypto'
+import { HttpResponse, http } from 'msw'
+import { setupServer } from 'msw/node'
+import type { FileUploadExtension } from '../extensions/FileUploadExtension'
+import { bufferToHex } from '../extensions/FileUploadExtension'
+import { test } from './fixtures'
+
+const server = setupServer(
+  http.put('https://localhost:3000/upload', async (info) => {
+    const contentType = info.request.headers.get('content-type')
+    const buffer = (await info.request.body?.getReader().read())?.value
+    if (buffer) {
+      const sha256 = bufferToHex(await crypto.subtle.digest('SHA-256', buffer.buffer))
+      return HttpResponse.json({
+        sha256,
+        url: `https://localhost:3000/${sha256}`,
+        type: contentType,
+        size: buffer?.buffer.byteLength,
+      })
+    }
+  }),
+)
+
+describe('FileUpload', () => {
+  beforeAll(() => {
+    server.listen()
+  })
+
+  afterAll(() => {
+    server.close()
+  })
+
+  afterEach(() => {
+    server.resetHandlers()
+  })
+
+  test('assert 2 successfully file uploads', async ({ editor, getFile }) => {
+    const fileUpload = editor.extensionManager.extensions.find(
+      (x) => x.name === 'fileUpload',
+    ) as typeof FileUploadExtension
+
+    const spySign = vitest.fn()
+    const spyHash = vitest.fn()
+    const spyStart = vitest.fn()
+    const spyUpload = vitest.fn()
+    const spyComplete = vitest.fn()
+
+    fileUpload.options.sign = spySign
+    fileUpload.options.hash = spyHash
+    fileUpload.options.onStart = spyStart
+    fileUpload.options.onUpload = spyUpload
+    fileUpload.options.onComplete = spyComplete
+
+    editor.setOptions()
+    const file = await getFile('test_upload.png')
+    const file2 = await getFile('test_upload2.png')
+
+    editor.commands.setContent('GM!')
+    editor.commands.addFile(file, editor.$doc.size - 2)
+    editor.commands.addFile(file2, editor.$doc.size - 2)
+
+    // less than ideal
+    await new Promise<void>((resolve) => setTimeout(() => resolve()))
+
+    const schema = editor.getJSON()
+
+    expect(schema.content).toHaveLength(3)
+    expect(schema.content?.[0]).toStrictEqual({ type: 'paragraph', content: [{ type: 'text', text: 'GM!' }] })
+    expect(schema.content?.[1].type).toBe('image')
+    expect(schema.content?.[1].attrs?.sha256).toBe(null)
+    expect(schema.content?.[1].attrs?.src).toContain('blob:nodedata')
+    expect(schema.content?.[2].type).toBe('image')
+    expect(schema.content?.[2].attrs?.sha256).toBe(null)
+    expect(schema.content?.[2].attrs?.src).toContain('blob:nodedata')
+
+    editor.commands.uploadFiles()
+
+    await new Promise<void>((resolve) => setTimeout(() => resolve(), 100))
+
+    const schema2 = editor.getJSON()
+    const hash1 = '008a2224c4d2a513ab2a4add09a2ac20c2d9cec1144b5111bc1317edb2366eac'
+    const hash2 = '6c36995913e97b73d5365f93a7b524a9e45edc68e4f11b78060154987c53602c'
+    expect(schema2.content?.[1].attrs?.sha256).toStrictEqual(hash1)
+    expect(schema2.content?.[1].attrs?.src).toStrictEqual(`https://localhost:3000/${hash1}`)
+    expect(schema2.content?.[2].attrs?.sha256).toStrictEqual(hash2)
+    expect(schema2.content?.[2].attrs?.src).toStrictEqual(`https://localhost:3000/${hash2}`)
+    const files = [
+      {
+        sha256: '008a2224c4d2a513ab2a4add09a2ac20c2d9cec1144b5111bc1317edb2366eac',
+        url: 'https://localhost:3000/008a2224c4d2a513ab2a4add09a2ac20c2d9cec1144b5111bc1317edb2366eac',
+        type: 'image/jpeg',
+        size: 16630,
+      },
+      {
+        sha256: '6c36995913e97b73d5365f93a7b524a9e45edc68e4f11b78060154987c53602c',
+        url: 'https://localhost:3000/6c36995913e97b73d5365f93a7b524a9e45edc68e4f11b78060154987c53602c',
+        type: 'image/jpeg',
+        size: 21792,
+      },
+    ]
+    expect(editor.storage.fileUpload).toStrictEqual({ files })
+
+    expect(spySign).toHaveBeenCalledTimes(2)
+    expect(spyHash).toHaveBeenCalledTimes(2)
+    expect(spyStart).toHaveBeenCalledOnce()
+    expect(spyUpload).toHaveBeenNthCalledWith(1, editor, files[0])
+    expect(spyUpload).toHaveBeenNthCalledWith(2, editor, files[1])
+    expect(spyComplete).toHaveBeenNthCalledWith(1, editor, files)
+
+    expect(editor.getText({ blockSeparator: ' ' })).toStrictEqual(
+      `GM! https://localhost:3000/008a2224c4d2a513ab2a4add09a2ac20c2d9cec1144b5111bc1317edb2366eac https://localhost:3000/6c36995913e97b73d5365f93a7b524a9e45edc68e4f11b78060154987c53602c`,
+    )
+  })
+})