This study aims to assess wireless network security holistically and attempts to determine the weakest link among the parts that comprise the ‘secure’ aspect of the wireless networks: security protocols, wireless technologies and user habits. The assessment of security protocols is done by determining the time taken to break a specific protocol’s encryption key, or to pass an access control by using brute force attack techniques. Passphrase strengths as well as encryption key strengths ranging from 40 to 256 bits are evaluated. Different scenarios are planned and created for passphrase generation, using different character sets and different number of characters. Then each scenario is evaluated based on the time taken to break that passphrase. At the end of the study, it is determined that the choice of the passphrase is the weakest part of the entire 802.11 wireless security system.