Email has become an essential means of communication. But it presents fertile ground for mistakes and missteps by lawyers and clients who might compromise attorney-client privilege by hitting the “Send” button before taking adequate precautions as to the recipients, as well as for unintended recipients who encounter such a mistake. Privilege issues stemming from email blunders and carelessness can create serious concerns for counsel and their clients, with courts often having to determine whether the disclosure of communication impairs privilege.

A collection of three cases from the past four years, discussed below, illustrates that email slip-ups are more common than one may think, and that even the briefest lapse in judgment or attention to detail can lead to highly problematic outcomes. The trio of cases is only a small sampling of the pitfalls that may affect even the most prudent attorney, and should suggest caution as to what accidents to avoid and what steps to take to prevent loss of privilege.

Mistaken Recipient

When sending an email, the recipient field presents a threshold hazard zone. In Simmions v. Pierless Fish Corp., 592 F. Supp. 3d 68 (E.D.N.Y. 2020), on the eve of mediation, defendants’ counsel mistakenly sent an email intended for her client to plaintiffs’ counsel, attaching specific litigation strategies and a detailed damages analysis. Defendants’ counsel’s client and plaintiffs’ counsel had the same first name.

The email contained material that would be protected by privilege, unless waived by voluntary disclosure. The court stated, “inadvertent disclosure of privileged material will be deemed a waiver when the disclosing party has failed to take adequate precautions to maintain the confidentiality of the privileged communication.” Id. at 73. (footnote omitted). The court outlined four factors - reasonableness of precautions taken, time to rectify the error, scope of discovery and extent of disclosure, and overarching issues of fairness - and held that the disclosure was excusable inadvertence, not a waiver of privilege. Further, the court found the disclosure understandably occurred because of “a common error that occurs frequently when using email; both the client and plaintiff’s counsel have the same first name and invariably, a simple click of the mouse on the wrong entry resulted in the email being sent to the wrong person.” Id. at 74.

Here, defendants’ counsel realized her email error within the hour and attempted to recall the email and contact her adversaries by email and phone requesting that they do not read, print, or forward the email and attachment. The court determined that “it does not appear that there was a clear disregard of the confidential nature of the documents on the part of defendants' counsel.” Id. The court reasoned that it will not find a waiver of privilege unless there is a showing of extreme carelessness, which it concluded was absent here, and ordered the destruction of the email and attachment and preclusion from use by plaintiffs.

The court’s reaction to certain acts of plaintiffs’ counsel is instructive as to potential problems to which the recipient of an unintended communication is exposed. The court considered whether the actions of plaintiffs’ counsel upon receipt of the inadvertent disclosure “justify the imposition of … disqualification from further representation in this case.” Id. at 73. Despite numerous attempts by defendants’ counsel to reach plaintiffs’ counsel after the disclosure, they did not respond and proceeded to not only read and discuss the email and attachment but also to upload the attachment to the firm’s document management system. The court noted that “the counsel knew - or should have known - that the dissemination of this email was likely to prejudice the defendants” and that there is a “high risk of trial taint because plaintiffs now possess defendants' litigation strategy.” Id. at 81. The court removed two of the attorneys involved from the case, directed other firm attorneys to submit affidavits attesting to their not having read or discussed the disclosures, and ordered that failure to produce such affidavits will result in the entire firm’s disqualification.

In another case involving an email mishap, Terpin v. Pinsky, No. 20 Civ. 3557, 2022 WL 3572928 (S.D.N.Y. Aug. 19, 2022), prospective litigation counsel for the defendant used a shortcut with initials in the recipient field intended to populate the email address of the firm’s controller that instead, erroneously, produced the address of plaintiff’s counsel. The email contained information regarding the payment method of a retainer.

Unlike Simmions, where the recipient attorney did not take protective measures after receiving the email despite opposing counsel’s prompt requests, plaintiff’s counsel in Terpin “prudently took steps to sequester the email, pledged not to use or disclose the information …, and promptly presented the issue to the court … for a determination of the claim, even in the absence of an assertion of privilege.” Id. at *2. The issue analyzed by the court in reaching its decision was whether the information in the email was privileged.

The court cited precedent, stating that "a long and unbroken line of cases in this Circuit have established that 'in the absence of special circumstances … fee arrangements do not fall within the attorney-client privilege because they are not the kinds of disclosures that would not have been made absent the privilege.'" Id. at *3. As the email contained no confidential information on litigation strategy or the nature or motive of proposed services, the court ruled that it was not privileged and denied an order for its destruction or preclusion of plaintiff’s counsel from using the email.

Voluntary or Inadvertent?

The final illustrative case explores how a client’s action, not an attorney’s conduct, may destroy the protections normally afforded to confidential attorney-client communications. In Semsysco GMBH v. GlobalFoundries Inc., No. 652719/2016, 2019 BL 100413 (Sup. Ct. N.Y. Cnty. Mar. 15, 2019), the CEO of one of the plaintiff corporations sent an email to one of the defendant corporations’ employees that had a lengthy email chain attached containing communications between the plaintiffs and their counsel. Plaintiffs’ counsel contended that the CEO only intended to forward the “top email” of the email chain, while the defendants argued that the CEO’s action was intentional and that the plaintiffs waived privilege.

The court stated: “The general rule that a disclosure of a privileged communication will operate as a waiver of the attorney-client privilege is subject to an exception where ‘it is shown that the client intended to maintain the confidentiality of the document, that reasonable steps were taken to prevent disclosure, that the party asserting the privilege acted promptly after discovering the disclosure to remedy the situation, and that the parties who received the documents will not suffer undue prejudice if a protective order against use of the document is issued.’” Id. at *2.

The CEO acknowledged that he deliberately sent the "top email" to the adversary’s employee to facilitate settlement discussions, but accidentally forwarded the privileged email chain containing litigation strategy and damages claims. Id. at *2-3. However, the court found the CEO’s statements to be “wholly conclusory” – the “top email” could not be understood without referring to the underlying emails. Id. at *3. The court observed that the plaintiffs failed to show that forwarding the email chain was inadvertent or that they acted promptly after discovering the disclosure, instead offering inconsistent statements about the timeframe in which the disclosure was discovered. Consequently, the court held the forwarded email chain to be a waiver of privilege, not an inadvertent disclosure.

Privilege is Precious

“If a client wishes to preserve the privilege, it must treat the confidentiality of attorney-client communications like jewels if not crown jewels," see Simmions. Emails containing privileged material must be handled with utmost care, by both the sender and the recipient.

Reprinted with permission from the January 26, 2023 edition of the New York Law Journal © 2023 ALM Media Properties, LLC. All rights reserved.