diff --git a/cypress/e2e/systemtags/files-inline-action.cy.ts b/cypress/e2e/systemtags/files-inline-action.cy.ts
new file mode 100644
index 0000000000000..f439a64ee7f3a
--- /dev/null
+++ b/cypress/e2e/systemtags/files-inline-action.cy.ts
@@ -0,0 +1,155 @@
+/* eslint-disable no-unused-expressions */
+/**
+ * SPDX-FileCopyrightText: 2024 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+import type { User } from '@nextcloud/cypress'
+import { randomBytes } from 'crypto'
+import { closeSidebar, getRowForFile, triggerActionForFile } from '../files/FilesUtils.ts'
+
+describe('Systemtags: Files integration', { testIsolation: true }, () => {
+	let user: User
+
+	beforeEach(() => cy.createRandomUser().then(($user) => {
+		user = $user
+
+		cy.mkdir(user, '/folder')
+		cy.uploadContent(user, new Blob([]), 'text/plain', '/file.txt')
+		cy.login(user)
+		cy.visit('/apps/files')
+	}))
+
+	it('See first assigned tag in the file list', () => {
+		const tag = randomBytes(8).toString('base64')
+
+		getRowForFile('file.txt').should('be.visible')
+		triggerActionForFile('file.txt', 'details')
+
+		cy.get('[data-cy-sidebar]')
+			.should('be.visible')
+			.findByRole('button', { name: 'Actions' })
+			.should('be.visible')
+			.click()
+
+		cy.findByRole('menuitem', { name: 'Tags' })
+			.should('be.visible')
+			.click()
+
+		cy.intercept('PUT', '**/remote.php/dav/systemtags-relations/files/**').as('assignTag')
+		cy.get('[data-cy-sidebar]')
+			.findByRole('combobox', { name: /collaborative tags/i })
+			.should('be.visible')
+			.type(`${tag}{enter}`)
+		cy.wait('@assignTag')
+		closeSidebar()
+
+		cy.reload()
+
+		getRowForFile('file.txt')
+			.findByRole('list', { name: /collaborative tags/i })
+			.findByRole('listitem')
+			.should('be.visible')
+			.and('contain.text', tag)
+	})
+
+	it('See two assigned tags are also shown in the file list', () => {
+		const tag1 = randomBytes(5).toString('base64')
+		const tag2 = randomBytes(5).toString('base64')
+
+		getRowForFile('file.txt').should('be.visible')
+		triggerActionForFile('file.txt', 'details')
+
+		cy.get('[data-cy-sidebar]')
+			.should('be.visible')
+			.findByRole('button', { name: 'Actions' })
+			.should('be.visible')
+			.click()
+
+		cy.findByRole('menuitem', { name: 'Tags' })
+			.should('be.visible')
+			.click()
+
+		cy.intercept('PUT', '**/remote.php/dav/systemtags-relations/files/**').as('assignTag')
+		cy.get('[data-cy-sidebar]').within(() => {
+			cy.findByRole('combobox', { name: /collaborative tags/i })
+				.should('be.visible')
+				.type(`${tag1}{enter}`)
+			cy.wait('@assignTag')
+			cy.findByRole('combobox', { name: /collaborative tags/i })
+				.should('be.visible')
+				.type(`${tag2}{enter}`)
+			cy.wait('@assignTag')
+		})
+
+		closeSidebar()
+		cy.reload()
+
+		getRowForFile('file.txt')
+			.findByRole('list', { name: /collaborative tags/i })
+			.children()
+			.should('have.length', 2)
+			.should('contain.text', tag1)
+			.should('contain.text', tag2)
+	})
+
+	it.only('See three assigned tags result in overflow entry', () => {
+		const tag1 = randomBytes(4).toString('base64')
+		const tag2 = randomBytes(4).toString('base64')
+		const tag3 = randomBytes(4).toString('base64')
+
+		getRowForFile('file.txt').should('be.visible')
+
+		cy.intercept('PROPFIND', '**/remote.php/dav/**').as('sidebarLoaded')
+		triggerActionForFile('file.txt', 'details')
+		cy.wait('@sidebarLoaded')
+
+		cy.get('[data-cy-sidebar]')
+			.should('be.visible')
+			.findByRole('button', { name: 'Actions' })
+			.should('be.visible')
+			.click()
+
+		cy.findByRole('menuitem', { name: 'Tags' })
+			.should('be.visible')
+			.click()
+
+		cy.intercept('PUT', '**/remote.php/dav/systemtags-relations/files/**').as('assignTag')
+		cy.get('[data-cy-sidebar]').within(() => {
+			cy.findByRole('combobox', { name: /collaborative tags/i })
+				.should('be.visible')
+				.type(`${tag1}{enter}`)
+			cy.wait('@assignTag')
+
+			cy.findByRole('combobox', { name: /collaborative tags/i })
+				.should('be.visible')
+				.type(`${tag2}{enter}`)
+			cy.wait('@assignTag')
+
+			cy.findByRole('combobox', { name: /collaborative tags/i })
+				.should('be.visible')
+				.type(`${tag3}{enter}`)
+			cy.wait('@assignTag')
+		})
+
+		closeSidebar()
+		cy.reload()
+
+		getRowForFile('file.txt')
+			.findByRole('list', { name: /collaborative tags/i })
+			.children()
+			.then(($children) => {
+				expect($children.length).to.eq(4)
+				expect($children.get(0)).be.visible
+				expect($children.get(1)).be.visible
+				// not visible - just for accessibility
+				expect($children.get(2)).not.be.visible
+				expect($children.get(3)).not.be.visible
+				// Text content
+				expect($children.get(1)).contain.text('+2')
+				// Remove the '+x' element
+				const elements = [$children.get(0), ...$children.get().slice(2)]
+					.map((el) => el.innerText.trim())
+				expect(elements).to.have.members([tag1, tag2, tag3])
+			})
+	})
+})
diff --git a/cypress/e2e/systemtags/files-sidebar.cy.ts b/cypress/e2e/systemtags/files-sidebar.cy.ts
new file mode 100644
index 0000000000000..c6e6fda50d452
--- /dev/null
+++ b/cypress/e2e/systemtags/files-sidebar.cy.ts
@@ -0,0 +1,44 @@
+/**
+ * SPDX-FileCopyrightText: 2024 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+
+import type { User } from '@nextcloud/cypress'
+import { randomBytes } from 'crypto'
+import { getRowForFile, triggerActionForFile } from '../files/FilesUtils.ts'
+
+describe('Systemtags: Files sidebar integration', { testIsolation: true }, () => {
+	let user: User
+
+	beforeEach(() => cy.createRandomUser().then(($user) => {
+		user = $user
+
+		cy.mkdir(user, '/folder')
+		cy.uploadContent(user, new Blob([]), 'text/plain', '/file.txt')
+		cy.login(user)
+	}))
+
+	it('Can assign tags using the sidebar', () => {
+		const tag = randomBytes(8).toString('base64')
+		cy.visit('/apps/files')
+
+		getRowForFile('file.txt').should('be.visible')
+		triggerActionForFile('file.txt', 'details')
+
+		cy.get('[data-cy-sidebar]')
+			.should('be.visible')
+			.findByRole('button', { name: 'Actions' })
+			.should('be.visible')
+			.click()
+
+		cy.findByRole('menuitem', { name: 'Tags' })
+			.click()
+
+		cy.intercept('PUT', '**/remote.php/dav/systemtags-relations/files/**').as('assignTag')
+		cy.get('[data-cy-sidebar]')
+			.findByRole('combobox', { name: /collaborative tags/i })
+			.should('be.visible')
+			.type(`${tag}{enter}`)
+		cy.wait('@assignTag')
+	})
+})