Most experts today and some State Bar Associations conclude that if the client and lawyer take reasonable precautions to protect confidentiality the fact that eavesdropping occurs on the Internet will not cause a waiver. However, as is the case with all privilege waiver issues, the courts will consider surrounding circumstances in reaching their decisions. However, they likewise opinion that the purpose is also served if the holder of the privilege feels the consequences of their carelessness in a disclosure when they cannot clearly demonstrate that continued protection is warranted. For some lawyers, concern lies with the potential temptation the courts may have in comparing E-mail to communications such as those conducted through cordless telephones. Many courts have concluded that there is no reasonable expectation to privacy in such communications.
Various tools are in fact available.
One approach is to use the password capability in your word processing software. If you are using software to compress the file in the zip format, that software will allow you to password protect the compressed file. Once your documents are transmitted, you can reveal your password via the telephone to your client. Another useful tool is encryption. Encryption is the process by which a key is mathematically applied to a source file to create an encrypted or scrambled version of the message or document.