diff --git a/cypress/e2e/outline.spec.js b/cypress/e2e/outline.spec.js
deleted file mode 100644
index b441a65d6b7..00000000000
--- a/cypress/e2e/outline.spec.js
+++ /dev/null
@@ -1,74 +0,0 @@
-import { randHash } from '../utils/index.js'
-
-const currentUser = randHash()
-
-const refresh = () => cy.get('.files-controls .crumb:not(.hidden) a')
-	.last()
-	.click({ force: true })
-
-const clickOutline = () => {
-	cy.getActionEntry('headings')
-		.click()
-
-	cy.get('.v-popper__wrapper .open').getActionEntry('outline')
-		.click()
-}
-
-const createMarkdown = (fileName, content) => {
-	return cy.createFile(fileName, content, 'text/markdown')
-		.then(refresh)
-}
-
-describe('Table of Contents', () => {
-	before(() => {
-		// Init user
-		cy.nextcloudCreateUser(currentUser, 'password')
-		cy.login(currentUser, 'password')
-	})
-
-	beforeEach(() => {
-		cy.login(currentUser, 'password')
-	})
-
-	it('sidebar toc', () => {
-		const fileName = 'toc.md'
-
-		createMarkdown(fileName, '# T1 \n ## T2 \n ### T3 \n #### T4 \n ##### T5 \n ###### T6')
-			.then(refresh)
-			.then(() => cy.openFile(fileName, { force: true }))
-			.then(clickOutline)
-
-		cy.getOutline()
-			.find('header')
-			.should('exist')
-
-		cy.getTOC()
-			.find('ul li')
-			.should('have.length', 6)
-		cy.getTOC()
-			.find('ul li')
-			.each((el, index) => {
-				cy.wrap(el)
-					.should('have.attr', 'data-toc-level')
-					.and('equal', String(index + 1))
-
-				cy.wrap(el)
-					.find('a')
-					.should('have.attr', 'href')
-					.and('equal', `#t${index + 1}`)
-			})
-	})
-
-	it('empty toc', () => {
-		const fileName = 'empty.md'
-
-		createMarkdown(fileName, '')
-			.then(refresh)
-			.then(() => cy.openFile(fileName, { force: true }))
-			.then(clickOutline)
-
-		cy.getOutline()
-			.find('ul')
-			.should('be.empty')
-	})
-})
diff --git a/cypress/e2e/sections.spec.js b/cypress/e2e/sections.spec.js
new file mode 100644
index 00000000000..89a3991a343
--- /dev/null
+++ b/cypress/e2e/sections.spec.js
@@ -0,0 +1,124 @@
+import { initUserAndFiles, randHash } from '../utils/index.js'
+
+const currentUser = randHash()
+const fileName = 'test.md'
+
+const refresh = () => cy.get('.files-controls .crumb:not(.hidden) a')
+	.last()
+	.click({ force: true })
+
+const clickOutline = () => {
+	cy.getActionEntry('headings')
+		.click()
+
+	cy.get('.v-popper__wrapper .open').getActionEntry('outline')
+		.click()
+}
+
+describe('Content Sections', () => {
+	before(function() {
+		initUserAndFiles(currentUser, fileName)
+	})
+
+	beforeEach(function() {
+		cy.login(currentUser, 'password', {
+			onBeforeLoad(win) {
+				cy.stub(win, 'open')
+					.as('winOpen')
+			},
+		})
+
+		cy.openFile(fileName)
+			.then(() => cy.clearContent())
+	})
+
+	describe('Heading anchors', () => {
+		beforeEach(() => cy.clearContent())
+
+		it('Anchor exists', () => {
+			cy.getContent()
+				.type('# Heading\nText\n## Heading 2\nText\n## Heading 2')
+				.then(() => {
+					cy.getContent()
+						.find('a.anchor-link')
+						.should(($anchor) => {
+							expect($anchor).to.have.length(3)
+							expect($anchor.eq(0)).to.have.attr('href').and.equal('#heading')
+							expect($anchor.eq(1)).to.have.attr('href').and.equal('#heading-2')
+							expect($anchor.eq(2)).to.have.attr('href').and.equal('#heading-2--1')
+						})
+				})
+		})
+
+		it('Anchor scrolls into view', () => {
+			// Create link to top heading
+			cy.getContent()
+				.type('{selectAll}{backspace}move top\n{selectAll}')
+				.get('.menububble button[data-text-bubble-action="add-link"]')
+				.click({ force: true })
+				.then(() => {
+					cy.get('.menububble .menububble__input')
+						.type('{shift}')
+						.type('#top{enter}', { force: true })
+				})
+			// Insert content above link
+			cy.getContent()
+				.type('{moveToStart}\n{moveToStart}# top \n')
+				.type('lorem ipsum \n'.repeat(25))
+				.type('{moveToEnd}\n')
+				.find('h1#top')
+				.should('not.be.inViewport')
+			// Click link and test view moved to anchor
+			cy.getContent()
+				.find('a:not(.anchor-link)')
+				.click()
+				.then(() => {
+					cy.getContent()
+						.get('h1[id="top"]')
+						.should('be.inViewport')
+				})
+		})
+	})
+
+	describe('Table of Contents', () => {
+		beforeEach(() => cy.clearContent())
+
+		it('sidebar toc', () => {
+			cy.getContent()
+				.type('# T1 \n## T2 \n### T3 \n#### T4 \n##### T5 \n###### T6\n')
+				.then(refresh)
+				.then(() => cy.openFile(fileName, { force: true }))
+				.then(clickOutline)
+
+			cy.getOutline()
+				.find('header')
+				.should('exist')
+
+			cy.getTOC()
+				.find('ul li')
+				.should('have.length', 6)
+			cy.getTOC()
+				.find('ul li')
+				.each((el, index) => {
+					cy.wrap(el)
+						.should('have.attr', 'data-toc-level')
+						.and('equal', String(index + 1))
+
+					cy.wrap(el)
+						.find('a')
+						.should('have.attr', 'href')
+						.and('equal', `#t${index + 1}`)
+				})
+		})
+
+		it('empty toc', () => {
+			refresh()
+				.then(() => cy.openFile(fileName, { force: true }))
+				.then(clickOutline)
+
+			cy.getOutline()
+				.find('ul')
+				.should('be.empty')
+		})
+	})
+})
diff --git a/cypress/support/chai.js b/cypress/support/chai.js
new file mode 100644
index 00000000000..77737e3bce2
--- /dev/null
+++ b/cypress/support/chai.js
@@ -0,0 +1,16 @@
+export default _chai => {
+	_chai.Assertion.addMethod('inViewport', function() {
+		const subject = this._obj
+
+		const height = Cypress.$(cy.state('window')).height()
+		const width = Cypress.$(cy.state('window')).width()
+		const rect = subject[0].getBoundingClientRect()
+
+		this.assert(
+			rect.top < height && rect.bottom > 0 && rect.right <= width && rect.left >= 0,
+			'expected #{this} to be in the viewport',
+			'expected #{this} to not be in the viewport',
+			this._obj
+		)
+	})
+}
diff --git a/cypress/support/commands.js b/cypress/support/commands.js
index fa5acc87774..9942fe29d06 100644
--- a/cypress/support/commands.js
+++ b/cypress/support/commands.js
@@ -258,8 +258,8 @@ Cypress.Commands.add('getTOC', () => {
 
 Cypress.Commands.add('clearContent', () => {
 	return cy.getContent()
-		.type('{selectall}')
-		.type('{del}')
+		.scrollIntoView()
+		.type('{selectAll}{backspace}', { force: true })
 })
 
 Cypress.Commands.add('openWorkspace', (subject, name) => {
diff --git a/cypress/support/e2e.js b/cypress/support/e2e.js
index 73c0c67db20..614793a739a 100644
--- a/cypress/support/e2e.js
+++ b/cypress/support/e2e.js
@@ -1,3 +1,8 @@
 // This file is loaded before all e2e tests
 
 import './commands.js'
+import chaiExtension from './chai.js'
+
+before(() => {
+	chai.use(chaiExtension)
+})