I have the same problem with 5.05 (we also use a Mac). We use Comcast cable internet connection, which limits attachments being sent to 10 MG, and anything larger than that I would get an error when trying to send it. I tried several different settings and setting the split to various sizes (including none) and also lowered the quality (which ultimately was inaudible at times). I had no where near the size of file as yours, so this is a problem with anything over 10MGs for us. I ended up limiting the dictation to under 3-4 minutes. This is not the solution, as I work in a law office, and documents can be very long. We just purchased a microphone, which has increased the quality 100%, so I will attempt to lower the quality of the file, hopefully increasing the time that can be dictated and sent, but this still will be limiting. Maybe NCH can suggest some "custom" compression settings? Otherwise, really happy with the software and recently purchased microphone through nch.