Oregon State Bar Bulletin — JULY 2009
Managing Your Practice
Sender, Beware:
E-mail Traps and Troubles
By Leonard D. DuBoff and Christy O. King

E-mail communications are extraordinarily efficient for lawyers — whether they are corresponding across town, across the country or around the world — but unfortunately they open the door to many pitfalls.

Although the American Bar Association has stated that sending unencrypted e-mail is not a per seviolation of an attorney’s duty to protect client confidences,1 e-mail users must be careful to avoid the ethical, legal and practical problems that can arise from using electronic correspondence.

It is quite common, for example, for attorneys to “carbon” (or “cc”) clients on e-mails to opposing counsel. If your e-mail cc’s the client, then when opposing counsel uses “reply to all,” that response will be transmitted to your client as well and may very well violate Oregon RPC 4.2, which prohibits direct communication with a represented party in most situations. To avoid this kind of problem, attorneys should blind copy (or “bcc”) their clients.

Clients should also be reminded not to reply to all when responding to an attorney’s communication because that reply may go not only to the lawyer for whom it is intended, but may also wind up being transmitted to opposing counsel and, perhaps, that attorney’s client as well.

Such a mistake can be devastating when the e-mail contains strategy, negotiating points or the like. This type of error can also waive the attorney-client privilege. In the event such an unfortunate happenstance does occur, the lawyer should immediately alert the party who inadvertently received the communication and request that it be deleted unread. By taking this action, it is likely that the attorney-client privilege would not be waived.

Oregon RPC 4.4(b) provides that:

A lawyer who receives a document relating to the representation of the lawyer’s client and knows or reasonably should know that the document was inadvertently sent shall promptly notify the sender.

This rule does not prohibit the receiver from claiming the right to retain the document, and an Oregon Ethics Opinion2 provides that whether the privilege has been waived by the inadvertent disclosure is a matter of law. A recent federal rule provides that inadvertent disclosure in a federal proceeding does not waiven the privilege if reasonable steps were taken to prevent disclosures and to rectify the error.3

With respect to an Oregon state court matter, Oregon Evidence Code 104(i) provides that: “Preliminary questions concerning the qualifications of a person to be a witness, the existence of a privilege or the admissibility of evidence shall be determined by the court.” A court determining whether a waiver has occurred should consider whether the disclosure was inadvertent, whether efforts were promptly made to remedy the error and whether preserving the privilege would be unfair to the opponent.4

Lawyers should also ensure that an e-mail sent to opposing counsel does not contain the stream of communications between the attorney and client that led to that communication. By providing the opposing counsel with the correspondence between you and your client, you may be once again compromising the attorney-client privilege. It is, therefore, appropriate for attorneys to have the intended communication to opposing counsel sent as a fresh e-mail rather than as part of the e-mail stream that led to it.

It is also important to carefully review e-mails before they are sent. In many e-mail programs, spellcheck does not catch misspellings in the subject lines of e-mails. Also, it corrects only spelling errors; that is, it does not determine whether the word is properly used (for instance, you is often typed for your). Thus, you may find that words in your e-mail are all correctly spelled, but they may not be used in the proper context or even make sense.

E-mail users are frequently careless with the subject line of their communication, which typically refers to the first communication. It is rare for recipients who respond to that communication to revise the subject line to reflect the response, which may be addressing other issues. As the stream of e-mails continue, the original subject line may become less and less relevant to the ultimate communication’s content, so it is a good idea to revise the subject accordingly.

Most lawyers have some form of standard disclaimer at the end of their e-mails. Frequently, this is automatically inserted by the attorney’s e-mail program. When e-mails are exchanged within the lawyer’s office so that a colleague or member of the firm’s support staff can assist in refining the communication, the program may automatically add an additional disclaimer. When this communication is then ultimately sent out, it may have two or more disclaimers stacked up at its end. This will alert an astute recipient to the fact that this communication has been wordsmithed by several people. To avoid this problem, you should delete any disclaimers that have accumulated at the end of the e-mail language.

When a lawyer receives an acrimonious e-mail or one from someone with whom there is a strained relationship, it is quite common to prepare a vitriolic response, which may ultimately prove embarrassing. It is for this reason that prudent attorneys will delay sending a response until they have either had time to cool off or can obtain input from colleagues who are more removed from the situation. Remember, your communications to opposing counsel may very well wind up as exhibits to pleadings, and you should ask yourself whether the communication you are about to send is something you would like to have read by the judge in your case, some other influential third party or even your own client.

While it is important to pay attention to the content of your e-mail and make sure that it effectively communicates just what you want to communicate, you should also pay attention to whom the communication is directed. When, for example, an attorney represents a business entity and the communication deals with subjects that should be restricted to certain individuals in that organization, care should be taken not to send the e-mail to a general e-mail box. Thus, in communicating with the CEO of a company regarding a possible business sale, you should not have that communication go to a secretary or general information box without first obtaining permission from the intended recipient. Nor should you send e-mails to an individual client at his/her work address without the express consent of the client, since many companies have policies providing that e-mail in their systems is not private and can be read by supervisors and others in the company. Similarly, an attorney who sends an e-mail to a family’s e-mail address when it is intended for just one of the family members could be waiving the attorney-client privilege in that communication, and if it involves a family dispute, there could be other serious consequences as well.

Autofill, the feature of some e-mail programs that automatically places a full e-mail address in the “To” or “cc” position once a few letters of that address/name are typed in, could also be problematic. If the attorney is not careful to confirm that the e-mail is actually directed to the right person, then the communication could easily go astray. For instance, you may have read about the lawyer for Eli Lilly & Co. who was trying to e-mail co-counsel Bradford Berenson with confidential information on settlement talks with the government but, instead, sent the communication to the New York Times reporter Alex Berenson.5

Metadata is another area of concern. Such information, which is invisible but retrievable, is often found in word processing documents and may include details such as editing time, comments, authors and even the edits themselves. The ABA has issued an ethics opinion stating that the receiving attorney is not prohibited from looking at metadata.6 Before sending an e-mail attachment, be sure to either convert the document to PDF or to use a metadata scrubbing program.

Law firms should have e-mail policies in firm handbooks covering a host of issues. These would include, among other things, the fact that the firm’s computer system belongs to it and e-mails received on it belong to the firm. Policies should also prohibit the use of profanity and other offensive, embarrassing or derogatory language, as well as all forms of harassment and discrimination. Other issues to cover include a prohibition on sending e-mails with viruses, worms or the like, or with content that infringes intellectual property or other rights.

Finally, attorneys should remember that merely deleting an e-mail does not expunge it from the system; rather, it remains on the hard drive until a special electronic scrubbing program is used to cleanse the hard drive or until the e-mail is overwritten by other data. Thus, you should be judicious when deciding whether to communicate via e-mail or through another less permanent form of communication.

Use of e-mail has become virtually universal within the legal community. This communication boom has, to some extent, leveled the playing field between large and small firms, though there is a host of items that should be considered when using this form of communication. We have tried to list many of the most common ones based on our experience and that of other members of the firm, but virtually every day we are provided with additional learning opportunities. Lawyers should be diligent when using their e-mail systems. It cannot be overemphasized how important it is to carefully read the final version of a communication before hitting send.


1. ABA Formal Op. 99-413 (1999).

2. OSB Formal Ethics Op. No. 2005-150.

3. Federal Rules of Evidence § 502.

4. Goldsborough v. Eagle Crest Partners, LTD., 314 Or. 336 (1992).

5. “Did Lawyer’s E-Mail Goof Land $1B Settlement on NYT’s Front Page?” at www.abajournal.com/news/lawyers_e_mail_goof_lands_on_nyts_fgront_page, 2/6/08; and “Lilly’s $1 Billion E-Mailstrom” at www.portfolio.com/news-markets/top-5/2008/02/05/Eli-Lilly-E-Mail-to-New-York-Times?, 2/5/08.

6. ABA Formal Op. 06-442 (2006).

Leonard DuBoff is author of more than 20 books on business and intellectual property law. He was a law professor for almost a quarter of a century, teaching at the Stanford and Lewis & Clark law schools. He is the managing principal of The DuBoff Law Group, which focuses on complex business and intellectual property. Christy King is a member of the DuBoff Law Group and editor-in-chief of the firm’s newsletter Critical Issues, and coauthor with DuBoff of the Deskbook of Art Law, Art Law in a Nutshell, The Law (In Plain English) for Restaurants and The Law (In Plain English) for Doctors, Dentists, and Other Health Care Professionals. Her practice areas include intellectual property, business and corporate law. For more information and to obtain a copy of the firm’s newsletter, see www.dubofflaw.com.

© 2009 Leonard D. DuBoff and Christy O. King

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