diff --git a/server-ce/test/history.spec.ts b/server-ce/test/history.spec.ts
new file mode 100644
index 0000000000..6e13c805d3
--- /dev/null
+++ b/server-ce/test/history.spec.ts
@@ -0,0 +1,84 @@
+import { createProject } from './helpers/project'
+import { throttledRecompile } from './helpers/compile'
+import { ensureUserExists, login } from './helpers/login'
+
+describe('History', function () {
+  ensureUserExists({ email: 'user@example.com' })
+  beforeEach(function () {
+    login('user@example.com')
+  })
+
+  function addLabel(name: string) {
+    cy.log(`add label ${JSON.stringify(name)}`)
+    cy.findByText('Labels').click()
+    cy.findAllByTestId('history-version-details')
+      .first()
+      .within(() => {
+        cy.get('button').click() // TODO: add test-id or aria-label
+        cy.findByText('Label this version').click()
+      })
+    cy.findByRole('dialog').within(() => {
+      cy.get('input[placeholder="New label name"]').type(`${name}{enter}`)
+    })
+  }
+
+  const CLASS_ADDITION = 'ol-cm-addition-marker'
+  const CLASS_DELETION = 'ol-cm-deletion-marker'
+
+  it('should support labels and comparison', () => {
+    cy.visit('/project')
+    createProject('labels')
+    const recompile = throttledRecompile()
+
+    cy.log('add content, including a line that will get removed soon')
+    cy.findByText('\\maketitle').parent().click()
+    cy.findByText('\\maketitle').parent().type('\n% added')
+    cy.findByText('\\maketitle').parent().type('\n% to be removed')
+    recompile()
+    cy.findByText('History').click()
+
+    cy.log('expect to see additions in history')
+    cy.get('.document-diff-container').within(() => {
+      cy.findByText('% to be removed').should('have.class', CLASS_ADDITION)
+      cy.findByText('% added').should('have.class', CLASS_ADDITION)
+    })
+
+    addLabel('Before removal')
+
+    cy.log('remove content')
+    cy.findByText('Back to editor').click()
+    cy.findByText('% to be removed').parent().type('{end}{shift}{upArrow}{del}')
+    recompile()
+    cy.findByText('History').click()
+
+    cy.log('expect to see annotation for newly removed content in history')
+    cy.get('.document-diff-container').within(() => {
+      cy.findByText('% to be removed').should('have.class', CLASS_DELETION)
+      cy.findByText('% added').should('not.have.class', CLASS_ADDITION)
+    })
+
+    addLabel('After removal')
+
+    cy.log('add more content after labeling')
+    cy.findByText('Back to editor').click()
+    cy.findByText('\\maketitle').parent().click()
+    cy.findByText('\\maketitle').parent().type('\n% more')
+    recompile()
+
+    cy.log('compare non current versions')
+    cy.findByText('History').click()
+    cy.findByText('Labels').click()
+    cy.findAllByTestId('compare-icon-version').last().click()
+    cy.findAllByTestId('compare-icon-version').filter(':visible').click()
+    cy.findByText('Compare up to this version').click()
+
+    cy.log(
+      'expect to see annotation for removed content between the two versions'
+    )
+    cy.get('.document-diff-container').within(() => {
+      cy.findByText('% to be removed').should('have.class', CLASS_DELETION)
+      cy.findByText('% added').should('not.have.class', CLASS_ADDITION)
+      cy.findByText('% more').should('not.exist')
+    })
+  })
+})