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I would never run a keystroke logger in an enterprise setting unless I first got a written approval from both an in-house lawyer and human resources personnel. The lawyer can check to make sure that your corporate policies, training and warning banners all limit an employee's presumption of privacy in the enterprise. The HR folks can similarly verify that reasonable suspicion of wrongdoing exists and warrants the use of a keystroke logger. In effect, the lawyer and HR review acts as a series of checks and balances on your actions. Don't view them as an annoying obstacle. Instead, realize that they are there to help you avoid a potential personal lawsuit from the target of your investigation!
This was first published in January 2008