From Convertino v. U.S. Dep’t of Justice, 2009 U.S. Dist. LEXIS 115050 (D.D.C. Dec. 10, 2009):

A party may waive either privilege by disclosing confidential information to a third-party, however, no waiver exists if "(1) the disclosure is inadvertent;" and "(2) the holder of the privilege or protection took reasonable steps to prevent disclosure." Fed. R. Evid. 502(b). In this case, the disclosure was inadvertent. Mr. Tukel had no intentions of allowing the DOJ, his employer, to read the e-mails he was sending to his personal attorney through his work e-mail account. *** Mr. Tukel also took steps to delete the e-mails as they were coming into his account--failing to realize that his employer had the e-mails. *** Additionally, since discovering that the DOJ still had access to his e-mails in April 2009, Mr. Tukel has taken reasonable steps to prevent disclosure to more parties by filing a motion and memorandum of law to intervene. ***

Mr. Tukel reasonably expected his e-mails with his personal attorney to remain confidential. *** Case law in this jurisdiction is not directly on point but New York gives the Court some direction. "[T]he question of privilege comes down to whether the intent to communicate in confidence was objectively reasonable." In re Asia Global Crossing, Ltd., 322 B.R. 247, 258 (S.D.N.Y. 2005). In order for documents sent through e-mail to be protected by the attorney-client privilege there must be a subjective expectation of confidentiality that is found to be objectively reasonable. See id. at 257 (outlining four factors to determine reasonableness; "(1) does the corporation maintain a policy banning personal or other objectionable use, (2) does the company monitor the use of the employee's computer or e-mail, (3) do third parties have a right of access to the computer or e-mails, and (4) did the corporation notify the employee, or was the employee aware, of the use and monitoring policies?"). Each case should be given an individualized look to see if the party requesting the protection of the privilege was reasonable in its actions. See Curto v. Med. World Commc'ns, Inc., No. 03-CV-6327, 2006 WL 1318387, *6 (E.D.N.Y. May 15, 2006); see also O'Connor v. Ortega, 480 U.S. 709, 718 (1987) ("Given the great variety of work environments, . . . the question whether an employee has a reasonable expectation of privacy must be addressed on a case-by-case basis.").

On the facts of this case, Mr. Tukel's expectation of privacy was reasonable. The DOJ maintains a policy that does not ban personal use of the company e-mail. Although the DOJ does have access to personal e-mails sent through this account, Mr. Tukel was unaware that they would be regularly accessing and saving e-mails sent from his account. *** Because his expectations were reasonable, Mr. Tukel's private e-mails will remain protected by the attorney-client privilege.