This paper presents a comparative analysis of password alternatives for enterprise authentication, emphasizing security, usability, and feasibility. Traditional password vulnerabilities, such as brute-force attacks, phishing, and password reuse, are scrutinized to establish the need for advanced methods. Alternatives evaluated include OTP apps, PKI tokens, smartcards, and YubiKey devices, with practical implementations assessed in a simulated enterprise environment for use cases like desktop logins, email access, web authentication, and SSH logins. The YubiKey emerges as a versatile “drop-in” solution, offering OTP generation, static password storage, and challenge-response functionalities, with minimal infrastructure changes. Smartcards and PKI tokens provide robust security but introduce higher deployment costs, while OTP apps present a balance between cost and convenience. Additionally, PAM USB and other tools highlight unique trade-offs in usability and security. The findings advocate for integrating multi-factor authentication solutions tailored to enterprise requirements. Future work is recommended to explore real-world deployments, centralized authentication systems, and the implications of adopting single-factor alternatives. This study underlines the critical role of user-centric design in fostering secure and efficient enterprise authentication systems.