Networks protected by firewalls and physical separation schemes are threatened by multi-homed devices. The purpose of this study is to detect multi-homed devices on a computer network. More specifically, the goal is to evaluate passive detection of multi-homed devices running various operating systems while communicating on a network. TCP timestamp data was used to estimate clock skews using linear regression and linear optimization methods. Analysis revealed that detection depends on the consistency of the estimated clock skew. Through vertical testing, it was also shown that clock skew consistency depends on the installed operating system. The linear programming and linear regression methods agree with one another when clock skews are consistent, indicating that linear regression is sufficient to identify multi-homed hosts in networks with low network delay. Further analysis showed inconsistencies of clock skew estimation on newer versions of OS X and free BSD 12.0 the clock skews from these operating systems prevented multi-homed fingerprinting using the proposed detection scheme.