For years, legal wiretapping was straightforward: the officer doing the intercept connected a tape recorder or the like to a single pair of wires. By the 1990s, however, the changing structure of telecommunications—there was no longer just “Ma Bell” to talk to—and new technologies such as ISDN and cellular telephony made executing a wiretap more complicated for law enforcement. Simple technologies would no longer suffice. In response, Congress passed the Communications Assistance for Law Enforcement Act (CALEA) which mandated a standardized lawful intercept interface on all local phone switches. Since its passage, technology has continued to progress, and in the face of new forms of communication—Skype, voice chat during multiplayer online games, instant messaging, etc.—law enforcement is again experiencing problems. The FBI has called this “Going Dark”: their loss of access to suspects’ communication. According to news reports, law enforcement wants changes to the wiretap laws to require a CALEA-like interface in Internet software. CALEA, though, has its own issues: it is complex software specifically intended to create a security hole—eavesdropping capability—in the already-complex environment of a phone switch. It has unfortunately made wiretapping easier for everyone, not just law enforcement. Congress failed to heed experts’ warnings of the danger posed by this mandated vulnerability, and time has proven the experts right. The so-called “Athens Affair,” where someone used the built-in lawful intercept mechanism to listen to the cell phone calls of high Greek officials, including the Prime Minister, is but one example. In an earlier work, we showed why extending CALEA to the Internet would create very serious problems, including the security problems it has visited on the phone system. In this paper, we explore the viability and implications of an alternative method for addressing law enforcements need to access communications: legalized hacking of target devices through existing vulnerabilities in end-user software and platforms. The FBI already uses this approach on a small scale; we expect that its use will increase, especially as centralized wiretapping capabilities become less viable. Relying on vulnerabilities and hacking poses a large set of legal and policy questions, some practical and some normative. Among these are: (1) Will it create disincentives to patching? (2) Will there be a negative effect on innovation? (Lessons from the so-called “Crypto Wars” of the 1990s, and in particular the debate over export controls on cryptography, are instructive here.) (3) Will law enforcement’s participation in vulnerabilities purchasing skew the market? (4) Do local and even state law enforcement agencies have the technical sophistication to develop and use exploits? If not, how should this be handled? A larger FBI role? (5) Should law enforcement even be participating in a market where many of the sellers and other buyers are themselves criminals? (6) What happens if these tools are captured and repurposed by miscreants? (7) Should we sanction otherwise illegal network activity to aid law enforcement? (8) Is the probability of success from such an approach too low for it to be useful? As we will show, these issues are indeed challenging. We regard the issues raised by using vulnerabilities as, on balance, preferable to adding more complexity and insecurity to online systems.