We all know the allure of email. Easy, rapid, mobile, less intrusive than a phone call, less laborious than a letter, the supremely flexible and ubiquitous facilitator of communication.

As generations raised on computers and email fill the ranks of executives and employees, businesses run more and more so on email. Unsurprisingly, so too does the legal profession. It is not at all uncommon today for a lawyer and client to do the great majority of their communicating over email. But with the convenience of email comes its downside: its ease encourages more of it; its ubiquity ensures that it will never fully go away. Where the attorney-client privilege was once easy to possess and safeguard – a private conversation in a conference room or over the phone; a discreet letter or file memorandum – the age of email has preserved and exposed it to breach. A recent decision by the Massachusetts Supreme Judicial Court offers a cautionary tale.

In Preventative Medicine Associates, Inc. v. Commonwealth, 465 Mass. 810 (2013), the SJC reviewed the conditions on which an ex parte search warrant could be used to seize and search the emails of a criminal defendant after he’d been indicted. The indictment was for Medicaid fraud. The search warrant that issued was for all emails in the defendant’s Gmail account over a three year period – over 68,500 emails in total. Only when the Attorney General produced one of these emails in pretrial discovery did the defendant’s lawyer catch wind of the search and seizure and move for a protective order.

The motion’s obvious and urgent basis: the concern that buried within the 68,500 emails were communications protected by the attorney-client privilege. The Attorney General claimed the office had taken steps to respect the privilege by running a search with the “names of attorneys and law firms believed by the prosecuting assistant attorneys general to have been associated with the defendants” and segregating out any emails registering hits, over 7,500 emails in total. The trial court, naturally unimpressed by this self-prescribed prophylactic, ordered the Attorney General’s office to cease its review of emails. The AG ultimately proposed to the Court what it claimed to be a more robust prophylactic: it would employ a “taint team” comprised of its own lawyers, but not layers involved in the prosecution, to review all emails and isolate those the team deemed protected by the attorney-client privilege. The issue presented to the SJC: did this adequately protect the privilege?

With some limitation that likely resonates more strongly in principle than in practice, the SJC answered yes. The SJC addressed this issue within the Fourth Amendment concern for improper searches and seizures. Of course, email flips the Fourth Amendment inquiry on its head: first the government seizes the email, then it searches it. The SJC addressed both events. First, with several caveats, it held that the government may use ex parte search warrants to seize the emails of a criminal defendant post-indictment. Second, it held that the government can search the seized emails as long as it first obtains the Superior Court’s approval of a search protocol designed “to protect against searches of privileged communications between the defendant and his attorneys.”

Acknowledging the irreparable harm that can follow a breach of the attorney-client privilege – including the violation of a defendant’s core Sixth Amendment right to effective assistance of counsel and a fair trial – the SJC went on to hold that “unless the Commonwealth can demonstrate a compelling contrary reason, the defendant must have an opportunity to be heard before the judge approves a particular search method.” Finally, the SJC ruled that the search protocol proposed in the case before it – the “taint team” procedure – satisfied the Fourth Amendment reasonable search requirement, but again within limits.

Most important among them, a defendant’s lawyer must have the opportunity to review and move to modify, if necessary, the email segregation made by the “taint team” before the emails deemed non-privileged are turned over to the prosecuting attorneys; and before the “taint team” method is even approved by the Superior Court, the Commonwealth must establish why this method is necessary over the sturdier protection of using an independent special master to review the emails before they are handed to prosecuting attorneys. While the SJC identified several factors that a court “may consider” in deciding whether the taint team method is necessary, it held in the case before it that the taint team approach employed by the AG’s office was permissible.

The inherent problem, however, and one that the limitations articulated by the SJC cannot address, is that these emails ended up in the hands of government to begin with. All Preventative Medicine Associates does is create a net to prevent privileged communications from reaching the prosecutor, but nets are not fortress walls, and ultimately they are only as reliable as the persons using them. Much better that an attorney need not have to rely on the integrity of a taint team protocol. It’s becoming a truism in our email age that a lawyer or client should never put in an email what can be said over the phone or in person. And even if that truism can’t entirely resist modern reality, lawyers will be well served by adopting more modest versions of it: resist the habit of using email for your most important and candid communications; and when email is necessary, instruct clients to conspicuously title their emails “Attorney-Client Privileged” and have them clearly and cleanly segregate their communications with you in separate, clearly titled folders, so that a “taint team” reviewing your clients’ inbox won’t have any defensible basis for tainting the attorney-client privilege.

This article first appeared on www.goulstonstorrs.com.