Even though webmail is insecure, the legal system usually treats communications via email as confidential for the purposes of attorney-client privilege.  What happens when good old Gmail caches emails between you and your attorney on your work computer, and your employer subsequently uses it against you in court?  No privilege for you!

A New Jersey Court recently wrestled with the issue.  Basically, the employer had a clear policy that company computers and communications were not private and the employee used Yahoo Mail to contact her attorney during work hours.  The employee quit, the company imaged her hard drive, the employee sued, and the company used the cached emails on her work hard drive against her in court.  The key language from the case:

The Court finds that when an employee has knowledge of the employer’s electronic communication policy which adequately warns that any and all internet use and communication conducted on the employer’s computer is not private to the employee and warns that E-mail and voice mail messages, internet use and communication and computer files are considered part of the company’s business and client records, such communications are not protected by such attorney client privilege and are then not to be considered private or personal to any individual employee.

Of course, this isn’t the law everywhere;  many places this issue is still relatively untested.  Still, word to the wise: watch out what you do on your employer’s computer.

The case is here, and some more in depth analysis can be found at Proskauer’s New Media Law Blog here.