Skype is A-OK for attorney-client privilege, right? Actually -- and you know this was coming -- it turns out the answer is a little more complicated than that.
As electronic communication supplants the many ways in which we communicate with each other (and our clients), it has forced us lawyers to become competent in the many ways in which it has complicated the profession. This is especially the case when it comes to issues of compliance and privilege. Prudent attorneys probably should assume that someone is always listening.
Old timey Skype worked on P2P (peer-to-peer) technology, which essentially allowed your desktop to communicate more or less directly with the PC on the other end of the conversation. Non-technical types (that's most of us) generally assumed that these conversations were private -- or they were too bewildered to even care. Surprise, not so much.
Rise of Mobile and Cloud
After acquiring Skype, Microsoft decided that it was time to get with the times and use the cloud. The problem is that there are few sources out there that seem to have any information on whether or not this new cloud-based Skype will have encryption or not. So far, mum's the word from Microsoft. This could be either because the technology is highly sensitive and they don't want IP vultures to get in on the action, or it could be that potential user won't like the answer and they're hoping people will stop asking. Lawyers, unfortunately, are in the "need to know" pile of folks.
Here's the thing, however. Yes, Skype is user friendly and a pleasant shade of blue -- but there are other means of communication that are encrypted -- so why would lawyers choose anything else? If they have an iPhone, why not enjoy end-to-end encryption built in? Or you can use WhatsApp. Why not that?