Abstract The escalating number of reported security susceptibilities taking advantage of the weaknesses of fixed or static password oriented authentication techniques, and the considerable financial/brand loss caused to the ventures due to those susceptibilities are only stressing the fact that the customary fixed password based authentication resolutions are no longer a sufficient shielding instrument for crucial enterprise applications. This calls for these ventures to critically investigate and embrace multi-factor, tougher, safe, dynamic one-time password based authentication expertise into their IT infrastructure. This article strikes a critical examination of the 2-Factor Authentication with a strong analytical exploration of the pros and cons accruing to this type of authentication. It is also worth noting that the dynamics in the contemporary society in the field of technologies have exposed the user of the services provided by the service-providers who depend on these technologies to dire vulnerabilities. These vulnerabilities expose the users to “man-in-the-middle attack.” This has therefore made the one level authentication methods for example the use of static passwords, use of fingerprints or even PIN untrustworthy. This is especially true after the Citibank’s scam scandal. Discussion Security experts and specialists have long flaunted the need for implementation of stringent security measures for the Web based transaction enterprises. At a glance, 2-Factor Authentication is the technique of human authentication where two factors are used to authenticate. Items like USB tokens and smart cards are increasingly being used in many organizations due to proliferation of online identity theft cases, (Yoon & Kee-Young, 2008). Fingerprints have been most authoritative method of authentication and have been known historically as an effective method of authentication. However recent developments in criminal activities have proved that this method is no longer worth all the trust. Tokens Biometrics The most common type of biometric data used in authentication is the thumbprint. However, this type of authentication is becoming multi-factor as biometric readers are added on the devices to provide comparison between two data strings during authentication process. This mode could prove to be quite costly especially where it involves a big number of users. Security Token Smart cards and USB tokens are the most common forms of security tokens. These security tokens make use of microcontroller technology, a security application, a secured storage area and an OS (Operating System). Phones This is a new category of token devices which involves 2-FA tool transforming the phone into the token device through SMS messaging or through by an interactive telephone call. The phone becomes a multi-factor authentication by the fact that the user communicates over two channels. This type of T-FA method reduces logistical costs considerably by scrapping off the need for separate hardware token device though the user incurs the cost of text messaging and data services and cellular calling minutes. Other types of the tokens include the Smart cards and the Universal Serial Bus which have been discussed above. In smart card, th