Wireless communication technologies, a dynamic transaction card, and a mobile application may be utilized to facilitate multi-factor authentication and secure electronic checkout of any website. A wireless connection between a dynamic transaction card and a user device may be utilized to authenticate a user. A user device application may be triggered to call, via an application programming interface (API), an account provider system, and this unique pairing may automatically facilitate payment to a merchant system associated with the electronic check out page. The account provider system may send a push notification to a browser extension associated with the checkout page to prompt the browser extension to populate fields on the electronic checkout page using user account information transmitted from the account provider system, providing a novel digital authentication framework that utilizes digital authentication techniques enables by user devices and dynamic transaction cards to seamlessly facilitate electronic checkout.