Even the most technology-challenged among us would have to admit that the ease with which we can communicate by e-mail is an improvement over the forms of correspondence that have preceded it. For most of us, there is no going back to the days before e-mail. This is no less true for communications between attorneys and clients than it is for other types of communications.

Two recent cases have shown that along with the speed and efficiency of e-mails between attorney and client can come legal headaches if great care is not taken to be sure that e-mails are sent to and seen by only the intended recipient.

Familiar e-mail tools–“cc,” to copy a message to one or more additional recipients; “bcc,” to blind copy a message without revealing any of the recipients’ e-mail addresses but the one in the “to” field; the “reply all” feature, to reply not only to the sender but to every recipient whom the sender “cc’d” or “bcc’d”; and the “auto-complete” function, a function that suggests or finishes an e-mail address when the sender begins to type it–all have the potential for causing problems.

Reply to All

In one case, defense counsel in a civil matter sent an e-mail to opposing counsel, with a “cc” to his own co-counsel and a “bcc” to his client, one of the defendants. The client responded, using the “reply all” function, thereby unwittingly transmitting his response simultaneously to opposing counsel as well as his own. The content of the response left no room for doubt that the client had intended his communication for his own counsel only. A mere 28 minutes later, the client’s counsel noticed what had happened and sent an e-mail to opposing counsel, demanding deletion of the e-mail. Opposing counsel declined.

When plaintiff’s counsel used the confidential e-mail as an exhibit in opposing the defendants’ partial summary judgment motion, the defense counsel moved to strike the e-mail. It did not help the defendants’ argument that the same attorney and client had made the same error on one previous occasion, some six months earlier. But it was unclear whether the defendant or his counsel had become aware of that prior incident at any time before receiving the opposition to the summary judgment motion.

In the end, the court granted the defendants’ motion to make the mistaken e-mail off-limits for any purpose in connection with the case. With the win, however, came an admonition from the court for the defendants and their lawyer: A client who wants to preserve the attorney-client privilege must be careful when using a means of communication having known and obvious risks of inadvertent disclosure, and the attorney should advise the client to that effect. A third such mistake, said the court, would not be met with such indulgence.

Beware of “Auto Complete”

E-mail mix-ups can be a double-edged sword, in that aggressively trying to gain an advantage upon receiving a privileged communication by mistake can backfire. That’s what happened, in a big way, in another case.

A group of engineers hired a law firm to protect them against interference from a former employer after they began their own business. The law firm accidentally sent a confidential e-mail to the engineers’ ex-employer. The mistake happened because an “auto-complete” function used by the law firm filled in an old e-mail address for one of the engineers.

When the misaddressed e-mail landed in the legal department for the former employer, some of its contents made their way into a counterclaim filed against the engineers by the former employer. That’s when the attorney for the engineers sought and was granted a far-reaching protective order from the court.

The former employer’s outside law firm was disqualified from the case, as was one of its in-house lawyers, and its general counsel was walled off from day-to-day management of the case because he had read the misdirected e-mail. The court required that the counterclaim be refiled with no references to the material from the e-mail. To top off the debacle for the former employer, it was required to pay thousands of dollars to the engineers, representing their attorney’s fees and costs expended in bringing the motion for a protective order.

The object lessons from these cases are clear: First, take care to avoid misdirecting e-mailed messages containing attorney-client communications; second, be equally careful not to treat such an e-mail that may fall into your lap by mistake as an opportunity to try to tip the scales of justice in your favor.