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The Perils and Pitfalls of Emailing and How to Avoid Them

Jonathan Joseph Walsh and Benjamin Clinton Woodruff

The Perils and Pitfalls of Emailing and How to Avoid Them
Mlenny via Getty Images

When it comes to embarrassing emails, politicians are not the only group making headlines. Lawyers are also being called to task for sending regrettable emails. Margaret Hartmann, “O’Reilly’s Team Accidentally Forwarded Strategy Emails to Reporter,” N.Y. Mag. (Apr. 21, 2017). Whether it is sending confidential information to the wrong recipient or choosing the wrong words to describe a client matter in an email, lawyers are more susceptible than ever to making mistakes that are captured forever in electronic form.

Email: Dangers Lurking One “Send” Click Away

Email has become the primary form of correspondence for most lawyers. Yet, it is easy for lawyers to forget that their emails may be read not just by the intended recipients but also by third parties in a different context. Indeed, a lawyer’s emails often become central to malpractice actions and attorney disciplinary hearings. For this reason, lawyers should not assume that their communications with their client or even within their firm are protected from disclosure.

Best Practices

Below are some suggested best practices for sending emails:

  • Before composing an email, consider picking up the phone or walking down the hall. Often, an in-person conversation is more effective and efficient than using email.
  • Use professional language and avoid jokes. Readers may misinterpret attempts at humor when viewed in a different context, such as an investigation or legal proceeding.
  • Avoid the use of ALL CAPS, exclamation points, abbreviations, and emoticons. Again, these types of emails may be misinterpreted in different contexts.
  • Proofread carefully before pressing “Send.” Use the spell checker and fill in the “To” and “Cc” lines after drafting and proofreading the email.
  • Make sure that the email is addressed to the right recipient. The autofill feature sometimes adds the wrong “John Smith.” Make sure that you are not sending a message to the wrong recipient, especially if contains confidential information.
  • Be careful with “Reply All.” Often, emails that are meant for only one recipient are sent to all recipients, disclosing information that should not be shared with those parties.
  • Use “Bcc” carefully. A “Bcc” recipient can and sometimes will hit “Reply All,” letting everyone know that recipient was blind copied. For this reason, the New York Bar Association has published an ethics opinion counseling attorneys not to BCC clients on emails with opposing counsel. Ethics Opinion 1076, N.Y. State Bar Ass’n (Dec. 8, 2015).
  • When including an attachment, be sure to include the correct attachment. Sending confidential information in an attachment to the wrong recipient can have dire consequences. See, e.g., “9 ‘Reply All’ Email Disasters,” Week (Nov. 13, 2009) (discussing a case in which the U.S. attorney sent the wrong attachment, revealing the identity of 24 confidential sources).
  • When corresponding with clients by email, do what you can to keep privileged information inside the attorney-client relationship. For example, advise clients not to forward your emails or memos to third parties.