diff --git a/.eslintrc.js b/.eslintrc.js
index aa3c4f4ac4..b3d3af9f9e 100644
--- a/.eslintrc.js
+++ b/.eslintrc.js
@@ -433,7 +433,7 @@ module.exports = {
     },
     {
       files: ['e2e/**/*.ts', 'e2e/**/*.js', 'e2e/**/*.jsx'],
-      rules: { 'import/no-extraneous-dependencies': 'off' },
+      rules: { 'import/no-extraneous-dependencies': 'off', 'no-unused-expressions': 'off' },
     },
   ],
 }
diff --git a/e2e/cypress.json b/e2e/cypress.json
index 72796c6643..e758cc30d6 100644
--- a/e2e/cypress.json
+++ b/e2e/cypress.json
@@ -1,4 +1,4 @@
 {
   "baseUrl": "http://localhost:1234",
-  "defaultCommandTimeout": 8000
+  "defaultCommandTimeout": 16000
 }
diff --git a/e2e/cypress/integration/dashboard-compressor.spec.ts b/e2e/cypress/integration/dashboard-compressor.spec.ts
index 8ebfff5510..0cc63fb228 100644
--- a/e2e/cypress/integration/dashboard-compressor.spec.ts
+++ b/e2e/cypress/integration/dashboard-compressor.spec.ts
@@ -14,7 +14,9 @@ function uglierBytes (text) {
     return Number(text.slice(0, -2))
   }
 
-  throw new Error(`Not what the computer thinks a human-readable size string look like:  ${text}`)
+  throw new Error(
+    `Not what the computer thinks a human-readable size string look like:  ${text}`,
+  )
 }
 
 describe('dashboard-compressor', () => {
@@ -33,27 +35,23 @@ describe('dashboard-compressor', () => {
       sizeBeforeCompression.push(uglierBytes(text))
     })
 
-    cy.get('.uppy-StatusBar-actionBtn--upload').click()
-
-    cy.get('.uppy-Informer p[role="alert"]', {
-      timeout: 12000,
-    }).should('be.visible')
-
     cy.window().then(({ uppy }) => {
-      for (const file of uppy.getFiles()) {
+      uppy.on('preprocess-complete', (file) => {
         expect(file.extension).to.equal('webp')
         expect(file.type).to.equal('image/webp')
-      }
-    })
 
-    cy.get('.uppy-Dashboard-Item-statusSize').should((elements) => {
-      expect(elements).to.have.length(sizeBeforeCompression.length)
+        cy.get('.uppy-Dashboard-Item-statusSize').should((elements) => {
+          expect(elements).to.have.length(sizeBeforeCompression.length)
+
+          for (let i = 0; i < elements.length; i++) {
+            expect(sizeBeforeCompression[i]).to.be.greaterThan(
+              uglierBytes(elements[i].textContent),
+            )
+          }
+        })
+      })
 
-      for (let i = 0; i < elements.length; i++) {
-        expect(sizeBeforeCompression[i]).to.be.greaterThan(
-          uglierBytes(elements[i].textContent),
-        )
-      }
+      cy.get('.uppy-StatusBar-actionBtn--upload').click()
     })
   })
 })
diff --git a/e2e/cypress/integration/dashboard-tus.spec.ts b/e2e/cypress/integration/dashboard-tus.spec.ts
index 8bbd16a437..6b561aaed2 100644
--- a/e2e/cypress/integration/dashboard-tus.spec.ts
+++ b/e2e/cypress/integration/dashboard-tus.spec.ts
@@ -4,6 +4,9 @@ type Tus = BaseTus & {
   requests: { isPaused: boolean }
 }
 
+// NOTE: we have to use different files to upload per test
+// because we are uploading to https://tusd.tusdemo.net,
+// constantly uploading the same images gives a different cached result (or something).
 describe('Dashboard with Tus', () => {
   beforeEach(() => {
     cy.visit('/dashboard-tus')
@@ -13,6 +16,29 @@ describe('Dashboard with Tus', () => {
     cy.intercept('http://localhost:3020/search/unsplash/*').as('unsplash')
   })
 
+  it.only('should emit `error` and `upload-error` events on failed POST request', () => {
+    cy.get('@file-input').attachFile(['images/traffic.jpg'])
+
+    const error = cy.spy()
+    const uploadError = cy.spy()
+    cy.window().then(({ uppy }) => {
+      uppy.on('upload-error', uploadError)
+      uppy.on('error', error)
+    })
+
+    cy.get('.uppy-StatusBar-actionBtn--upload').click()
+
+    cy.intercept(
+      { method: 'POST', url: 'https://tusd.tusdemo.net/*', times: 1 },
+      { statusCode: 401, body: { code: 401, message: 'Expired JWT Token' } },
+    ).as('post')
+
+    cy.wait('@post').then(() =>  {
+      expect(error).to.be.called
+      expect(uploadError).to.be.called
+    })
+  })
+
   it('should upload cat image successfully', () => {
     cy.get('@file-input').attachFile('images/cat.jpg')
     cy.get('.uppy-StatusBar-actionBtn--upload').click()
@@ -23,7 +49,7 @@ describe('Dashboard with Tus', () => {
   })
 
   it('should start exponential backoff when receiving HTTP 429', () => {
-    cy.get('@file-input').attachFile(['images/cat.jpg', 'images/traffic.jpg'])
+    cy.get('@file-input').attachFile(['images/baboon.png'])
     cy.get('.uppy-StatusBar-actionBtn--upload').click()
 
     cy.intercept(
diff --git a/packages/@uppy/core/types/index.d.ts b/packages/@uppy/core/types/index.d.ts
index 71bcf1597f..f34b200e0b 100644
--- a/packages/@uppy/core/types/index.d.ts
+++ b/packages/@uppy/core/types/index.d.ts
@@ -210,6 +210,7 @@ export type FilesAddedCallback<TMeta> = (files: UppyFile<TMeta>[]) => void;
 export type FileRemovedCallback<TMeta> = (file: UppyFile<TMeta>, reason: FileRemoveReason) => void;
 export type UploadCallback = (data: { id: string, fileIDs: string[] }) => void;
 export type ProgressCallback = (progress: number) => void;
+export type PreProcessCompleteCallback<TMeta> = (file: UppyFile<TMeta>) => void;
 export type UploadProgressCallback<TMeta> = (file: UppyFile<TMeta>, progress: FileProgress) => void;
 export type UploadSuccessCallback<TMeta> = (file: UppyFile<TMeta>, response: SuccessResponse) => void
 export type UploadCompleteCallback<TMeta> = (result: UploadResult<TMeta>) => void
@@ -225,6 +226,7 @@ export interface UppyEventMap<TMeta = Record<string, unknown>> {
   'file-removed': FileRemovedCallback<TMeta>
   'upload': UploadCallback
   'progress': ProgressCallback
+  'preprocess-complete': PreProcessCompleteCallback<TMeta>
   'upload-progress': UploadProgressCallback<TMeta>
   'upload-success': UploadSuccessCallback<TMeta>
   'complete': UploadCompleteCallback<TMeta>
diff --git a/yarn.lock b/yarn.lock
index 20b8a77094..7b4f5646ca 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -16643,8 +16643,8 @@ __metadata:
   linkType: hard
 
 "cypress@npm:^9.0.0":
-  version: 9.5.2
-  resolution: "cypress@npm:9.5.2"
+  version: 9.6.0
+  resolution: "cypress@npm:9.6.0"
   dependencies:
     "@cypress/request": ^2.88.10
     "@cypress/xvfb": ^1.2.4
@@ -16678,7 +16678,7 @@ __metadata:
     listr2: ^3.8.3
     lodash: ^4.17.21
     log-symbols: ^4.0.0
-    minimist: ^1.2.5
+    minimist: ^1.2.6
     ospath: ^1.2.2
     pretty-bytes: ^5.6.0
     proxy-from-env: 1.0.0
@@ -16690,7 +16690,7 @@ __metadata:
     yauzl: ^2.10.0
   bin:
     cypress: bin/cypress
-  checksum: d19a183df25adcb87ba4914fb177a2b8bf2f004c8364fa21abb6bf66f2462d6f586bf09b58480e804f6b499281d931712a3e262f09880859e3170d513c5c9227
+  checksum: 1e5142885a3fb54db6ef7477e3b11b363f1f610ff008982af014e6df3261ac3899f4cad407c598fb690f93029634adb4ad4605929d10776f92175a3eebb471c4
   languageName: node
   linkType: hard