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diff --git a/cypress/e2e/files_sharing/expiry-date.cy.ts b/cypress/e2e/files_sharing/expiry-date.cy.ts
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+++ b/cypress/e2e/files_sharing/expiry-date.cy.ts
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+/*!
+ * SPDX-FileCopyrightText: 2025 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+
+import { User } from '@nextcloud/cypress'
+import { closeSidebar } from '../files/FilesUtils.ts'
+import { createShare, openSharingDetails, openSharingPanel, updateShare } from './FilesSharingUtils.ts'
+
+describe('files_sharing: Expiry date', () => {
+	const expectedDefaultDate = new Date(Date.now() + 2 * 24 * 60 * 60 * 1000)
+	const expectedDefaultDateString = `${expectedDefaultDate.getFullYear()}-${String(expectedDefaultDate.getMonth() + 1).padStart(2, '0')}-${String(expectedDefaultDate.getDate()).padStart(2, '0')}`
+	const fortnight = new Date(Date.now() + 14 * 24 * 60 * 60 * 1000)
+	const fortnightString = `${fortnight.getFullYear()}-${String(fortnight.getMonth() + 1).padStart(2, '0')}-${String(fortnight.getDate()).padStart(2, '0')}`
+
+	let alice: User
+	let bob: User
+
+	before(() => {
+		// Ensure we have the admin setting setup for default dates with 2 days in the future
+		cy.runOccCommand('config:app:set --value yes core shareapi_default_internal_expire_date')
+		cy.runOccCommand('config:app:set --value 2 core shareapi_internal_expire_after_n_days')
+
+		cy.createRandomUser().then((user) => {
+			alice = user
+			cy.login(alice)
+		})
+		cy.createRandomUser().then((user) => {
+			bob = user
+		})
+	})
+
+	after(() => {
+		cy.runOccCommand('config:app:delete core shareapi_default_internal_expire_date')
+		cy.runOccCommand('config:app:delete core shareapi_enforce_internal_expire_date')
+		cy.runOccCommand('config:app:delete core shareapi_internal_expire_after_n_days')
+	})
+
+	beforeEach(() => {
+		cy.runOccCommand('config:app:delete core shareapi_enforce_internal_expire_date')
+	})
+
+	it('See default expiry date is set and enforced', () => {
+		// Enforce the date
+		cy.runOccCommand('config:app:set --value yes core shareapi_enforce_internal_expire_date')
+		const dir = 'defaultExpiryDateEnforced'
+		prepareDirectory(dir)
+
+		validateExpiryDate(dir, expectedDefaultDateString)
+		cy.findByRole('checkbox', { name: /expiration date/i })
+			.should('be.checked')
+			.and('be.disabled')
+	})
+
+	it('See default expiry date is set also if not enforced', () => {
+		const dir = 'defaultExpiryDate'
+		prepareDirectory(dir)
+
+		validateExpiryDate(dir, expectedDefaultDateString)
+		cy.findByRole('checkbox', { name: /expiration date/i })
+			.should('be.checked')
+			.and('not.be.disabled')
+			.check({ force: true, scrollBehavior: 'nearest' })
+	})
+
+	it('Can set custom expiry date', () => {
+		const dir = 'customExpiryDate'
+		prepareDirectory(dir)
+		updateShare(dir, 0, { expiryDate: fortnight })
+		validateExpiryDate(dir, fortnightString)
+	})
+
+	it('Custom expiry date survives reload', () => {
+		const dir = 'customExpiryDateReload'
+		prepareDirectory(dir)
+		updateShare(dir, 0, { expiryDate: fortnight })
+		validateExpiryDate(dir, fortnightString)
+
+		cy.visit('/apps/files')
+		validateExpiryDate(dir, fortnightString)
+	})
+
+	/**
+	 * Regression test for https://github.com/nextcloud/server/pull/50192
+	 * Ensure that admin default settings do not always override the user set value.
+	 */
+	it('Custom expiry date survives unrelated update', () => {
+		const dir = 'customExpiryUnrelatedChanges'
+		prepareDirectory(dir)
+		updateShare(dir, 0, { expiryDate: fortnight })
+		validateExpiryDate(dir, fortnightString)
+
+		closeSidebar()
+		updateShare(dir, 0, { note: 'Only note changed' })
+		validateExpiryDate(dir, fortnightString)
+
+		cy.visit('/apps/files')
+		validateExpiryDate(dir, fortnightString)
+	})
+
+	/**
+	 * Prepare directory, login and share to bob
+	 *
+	 * @param name The directory name
+	 */
+	function prepareDirectory(name: string) {
+		cy.mkdir(alice, `/${name}`)
+		cy.login(alice)
+		cy.visit('/apps/files')
+		createShare(name, bob.userId)
+	}
+
+	/**
+	 * Validate expiry date on a share
+	 *
+	 * @param filename The filename to validate
+	 * @param expectedDate The expected date in YYYY-MM-dd
+	 */
+	function validateExpiryDate(filename: string, expectedDate: string) {
+		openSharingPanel(filename)
+		openSharingDetails(0)
+
+		cy.get('#share-date-picker')
+			.should('exist')
+			.and('have.value', expectedDate)
+	}
+
+})