Digital voices aren't going to sound like real voices for a long time. The technology isn't there and Jen is going to have a hard time going through every phoneme. For example, there are several different /p/ sounds in english. Some have air with them and some don't. Then the computer needs to be told where those sounds go and when. To be honest. It's a lot of work, so only some key phrases will be in Jen Taylor's voice. Cortana is also being released as a beta, so that is another thing to be aware of.