My wife is the one who did all our CDs, but I'm pretty sure that there is an option for it to go onto the internet and download all the CD and song info, because when we play them on either our Roku, or on my wife's little audio gadget, or even on our Sirius receiver, the CD name, performer name, and song name are all displayed. I wasn't sure if the Azbox would do the same, but I just tried it, and when it plays a song, it shows CD artist title and genre I think the track was left blank, but since it had the title, I think that replaces track.
I think if that program can't access the internet, then it just leaves the song info blank. But again, I'm not real positive, because my wife did all the CD--> MP3 conversions.
Perhaps on your CD the songs overlap tracks somehow, because I've never noticed it cutting off the end of songs, but I'll ask my wife if she's noticed that.
I can't remember if we're using the free version of that program or if we paid to upgrade it, but it's worked perfectly for what we do. Really makes accessing many hundreds of CDs easy. We have them all on one hard drive, and move them to thumbdrives or those little memory cards, or just play them over the network. I'm not sure if the Azbox can detect one of those UP&P servers or whatever they call them, but we have a shareware server on the computer which has some extra features with respect to displaying and playing songs, if you don't want to just play one CD at a time.