Although the literature for the iPod Classic 160 GB (last generation) talks about 40,000 songs being added, it's not clear to me that's actually possible. I have a large classical collection set up under Stan Brown's Taming Itunes for Classical Music method, and with all the large cheap classical boxes coming out, my collection has gotten pretty enormous. My iPod Classic 160GB isn't anywhere near full---probably 2/3 full since I have everything at 128kbps, but when I get close to 30,000 "songs" (actually movements in my case but the distinction shouldn't matter), it starts crapping out. It locks up more and more, and recently I had to reformat the drive to get it to work at all. The same thing happens with my secondary iPod Classic, so it's probably not a mechanical or HDD problem. Using Google, I found this forum, which suggests that there's a hard limit of 2^15 songs (a bit over 30,000)--or at least there was, since it's from a few years ago : http://www.rapidrepair.com/phpbb/viewtopic.php?f=2&t=2508&start=20 They're talking about modded rather than stock iPods, but it also sounds like a limitation of the iPod software itself. Can anyone verify this? Is anyone successfully using more than 30,000 songs on a 160GB Classic? I know Kirk also has a massive classical collection too, so I'd like to know what limits he's pushing, but anyone else's input is certainly welcome. Along the same lines, is there an upper limit to playlists and smart playlists? I saw something that suggested the cap was somewhere near 20,000 but I can't remember where I saw that. One of my not-recently-played playlists is in that neighborhood, so that could also be causing my problems. I am going to do some experimentation as I rebuild this iPod, and maybe will add 15,000 or so song limits to my smart playlists just to be safe, but if someone has already run into this issue and found a workaround, I'd appreciate knowing so I don't have to reinvent this wheel.