Organizations are repeatedly embarrassed when their sensitive digital documents go public or fall into the hands of adversaries, often as a result of unintentional or inadvertent leakage. Such leakage has been traditionally handled either by preventive means, which are evidently not hermetic, or by punitive measures taken after the main damage has already been done. Yet, the challenge of preventing a leaked file from spreading further among computers and over the Internet is not resolved by existing approaches. This paper presents a novel method, which aims at reducing and limiting the potential damage of a leakage that has already occurred. The main idea is to tag sensitive documents within the organization’s boundaries by attaching a benign detectable malware signature (DMS). While the DMS is masked inside the organization, if a tagged document is somehow leaked out of the organization’s boundaries, common security services such as Anti-Virus (AV) programs, firewalls or email gateways will detect the file as a real threat and will consequently delete or quarantine it, preventing it from spreading further. This paper discusses various aspects of the DMS, such as signature type and attachment techniques, along with proper design considerations and implementation issues. The proposed method was implemented and successfully tested on various file types including documents, spreadsheets, presentations, images, executable binaries and textual source code. The evaluation results have demonstrated its effectiveness in limiting the spread of leaked documents.