diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress.json b/src/Umbraco.Tests.AcceptanceTest/cypress.json
index 33978211edca..340eede2a03d 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress.json
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress.json
@@ -7,5 +7,9 @@
         "password": "<insert password in cypress.env.json>"
     },
     "supportFile": "cypress/support/index.ts",
-    "videoUploadOnPasses" : false
+    "videoUploadOnPasses" : false,
+    "retries": {
+      "runMode": 5,
+      "openMode": 1
+    }
 }
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/documentTypes.ts b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/documentTypes.ts
index 1a86e908528c..fa4c6ec9a3cc 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/documentTypes.ts
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/documentTypes.ts
@@ -35,7 +35,7 @@ context('Document Types', () => {
     cy.get('#datatype-search').type('Textstring');
 
     // Choose first item
-    cy.get('ul.umb-card-grid li [title="Textstring"]').closest("li").click();
+    cy.get('ul.umb-card-grid [title="Textstring"]').closest("li").click();
 
     // Save property
     cy.get('.btn-success').last().click();
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/mediaTypes.ts b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/mediaTypes.ts
index 4064c1f41e87..385a70bd5b3b 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/mediaTypes.ts
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/mediaTypes.ts
@@ -34,7 +34,7 @@ context('Media Types', () => {
     cy.get('#datatype-search').type('Textstring');
 
     // Choose first item
-    cy.get('ul.umb-card-grid li [title="Textstring"]').closest("li").click();
+    cy.get('ul.umb-card-grid [title="Textstring"]').closest("li").click();
 
     // Save property
     cy.get('.btn-success').last().click();
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/memberTypes.ts b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/memberTypes.ts
index e84c29c0d8b1..4dcc80432e36 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/memberTypes.ts
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Settings/memberTypes.ts
@@ -32,7 +32,7 @@ context('Member Types', () => {
     cy.get('#datatype-search').type('Textstring');
 
     // Choose first item
-    cy.get('ul.umb-card-grid li [title="Textstring"]').closest("li").click();
+    cy.get('ul.umb-card-grid [title="Textstring"]').closest("li").click();
 
     // Save property
     cy.get('.btn-success').last().click();
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Tour/backofficeTour.ts b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Tours/backofficeTour.ts
similarity index 100%
rename from src/Umbraco.Tests.AcceptanceTest/cypress/integration/Tour/backofficeTour.ts
rename to src/Umbraco.Tests.AcceptanceTest/cypress/integration/Tours/backofficeTour.ts
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Users/userGroups.js b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Users/userGroups.js
index afef0e7701f7..ce2e366f2c66 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Users/userGroups.js
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress/integration/Users/userGroups.js
@@ -19,7 +19,7 @@ context('User Groups', () => {
 
     // Assign sections
     cy.get('.umb-box:nth-child(1) .umb-property:nth-child(1) localize').click();
-    cy.get('.umb-tree-item span').click({multiple:true});
+    cy.get('.umb-tree-item__inner').click({multiple:true, timeout: 10000});
     cy.get('.btn-success').last().click();
 
     // Save
diff --git a/src/Umbraco.Tests.AcceptanceTest/cypress/plugins/index.js b/src/Umbraco.Tests.AcceptanceTest/cypress/plugins/index.js
index 59283feec5c2..51b79a1fef46 100644
--- a/src/Umbraco.Tests.AcceptanceTest/cypress/plugins/index.js
+++ b/src/Umbraco.Tests.AcceptanceTest/cypress/plugins/index.js
@@ -11,6 +11,7 @@
 
 // This function is called when a project is opened or re-opened (e.g. due to
 // the project's config changing)
+const del = require('del')
 
 /**
  * @type {Cypress.PluginConfig}
@@ -24,5 +25,13 @@ module.exports = (on, config) => {
     config.baseUrl = baseUrl;
   }
 
+  on('after:spec', (spec, results) => {
+    if(results.stats.failures === 0 && results.video) {
+      // `del()` returns a promise, so it's important to return it to ensure
+      // deleting the video is finished before moving
+      return del(results.video)
+    }
+  })
+
   return config;
 }
diff --git a/src/Umbraco.Tests.AcceptanceTest/package.json b/src/Umbraco.Tests.AcceptanceTest/package.json
index fd401c72c0cd..3b9b2864e1c9 100644
--- a/src/Umbraco.Tests.AcceptanceTest/package.json
+++ b/src/Umbraco.Tests.AcceptanceTest/package.json
@@ -9,11 +9,11 @@
   },
   "devDependencies": {
     "cross-env": "^7.0.2",
-    "cypress": "8.4.1",
+    "cypress": "^8.7.0",
     "del": "^6.0.0",
     "ncp": "^2.0.0",
     "prompt": "^1.2.0",
-    "umbraco-cypress-testhelpers": "^1.0.0-beta-58"
+    "umbraco-cypress-testhelpers": "^1.0.0-beta-60"
   },
   "dependencies": {
     "typescript": "^3.9.2"