diff --git a/site/cypress/e2e/Cypress-UI/sidebar.spec.js b/site/cypress/e2e/Cypress-UI/sidebar.spec.js
index bfbee31863a..7adcae3b9af 100644
--- a/site/cypress/e2e/Cypress-UI/sidebar.spec.js
+++ b/site/cypress/e2e/Cypress-UI/sidebar.spec.js
@@ -99,7 +99,6 @@ function baseCourseSidebar(user, course) {
 }
 
 describe('Test sidebars', () => {
-    // Sample Course
     it('Test student sidebars', () => {
         baseCourseSidebar('student', 'sample');
         baseSidebar();
@@ -133,17 +132,21 @@ describe('Test sidebars', () => {
         // assert that we dont begin with any custom sidebar elements
         sidebarElements.forEach((element) => {
             cy.get(`[data-testid="${element}-delete-button"]`).should('not.exist');
-            cy.get(`[data-testid="${element}-upload-input"]`).attachFile(`copy_of_sample_files/site_theme/${element}`);
+            cy.get(`[data-testid="${element}-upload-input"]`).selectFile(`cypress/fixtures/copy_of_sample_files/site_theme/${element}`);
             cy.get(`[data-testid="${element}-upload-button"]`).click();
+            cy.get(`[data-testid="${element}-delete-button"]`).should('exist');
         });
-
+        sidebarContainsButton('Syllabus', 'http://www.cs.rpi.edu/academics/courses/fall18/csci1200/syllabus.php');
+        cy.logout();
         ['student', 'ta', 'instructor', 'grader'].forEach((user) => {
             cy.login(user);
             cy.visit(['sample']);
             extendedBaseSidebar();
             cy.get('body').should('have.css', 'background-image').and('include', 'http://www.cs.rpi.edu/~cutler/classes/visualization/S18/images/vinca_minor_mirrored.jpg');
             cy.get('#submitty-body').should('have.css', 'background-color', 'rgba(240, 240, 240, 0.85)');
+            cy.logout();
         });
+        cy.logout();
 
         cy.login('instructor');
         cy.visit(['sample', 'theme']);