diff --git a/cypress/integration/routing/index-file.spec.js b/cypress/integration/routing/index-file.spec.js
index bddf9cbce..3aeb0438f 100644
--- a/cypress/integration/routing/index-file.spec.js
+++ b/cypress/integration/routing/index-file.spec.js
@@ -6,4 +6,33 @@ context('routing.indexFile', () => {
 
     cy.get('#main').should('contain', 'Bug Fixes');
   })
+
+  it('handles index file routing with fragments', () => {
+    cy.visit('http://localhost:3000/index.html#/');
+
+    cy.get('.sidebar-nav').contains('Changelog').click();
+
+    cy.get('#main').should('contain', 'Bug Fixes');
+  })
+
+  it('returns 404 for index file with leading fragment', () => {
+    cy.visit('http://localhost:3000/#/index.html/');
+
+    cy.get('#main').should('contain', '404');
+  })
+
+  it('returns 500 for index file as folder', () => {
+    cy.request({
+      url: 'http://localhost:3000/index.html/#/',
+      failOnStatusCode: false
+    }).then((resp) => expect(500).to.eq(resp.status))
+  })
+
+
+  it('does not serve shadowing index markdown file', () => {
+    cy.request({
+      url: 'http://localhost:3000/index.md',
+      failOnStatusCode: false
+    }).then((resp) => expect(404).to.eq(resp.status))
+  })
 });