Legislative requirements like those in the Sarbanes-Oxley Act have sharply increased the incidence of monitoring of electronic communications, but the consequences of this trend are little understood. This study examines the impact of organizational monitoring of sensitive instant message (IM) discussions with a designed experiment. When their IMs are known to be monitored, individuals are found to sharply curtail their discussion of personally incriminating information and to increase their spontaneous denials of knowledge of sensitive topics. Surprisingly, perhaps, they also increase their discussion of relayed information that may incriminate others or the organization. Qualitative analysis suggests that people are not aware they make these adjustments to their IM communication content when monitored. Given the legislative compliance motivations for some of the monitoring activity in companies, it is ironic that study findings suggest organizations may communicate less firsthand information about potentially curtailable legal liabilities and other sensitive incidents requiring corrective action when communication is monitored. Organizations enacting monitoring of IM should pay heed to the requirements as well as the discretion available to them within those requirements to enact monitoring in a way that suits their organizational goals.