Unfortunately no. This is bar far the worst thing about iTunes. - Chris Nixon

Of course there is. Download iTLU (iTunes Library Updater). There is a gui as well as a command line interface, you can write a batch and then set when you want it to run with Task Scheduler. - Joel Tanner

To the best of my knowledge, Thomas, there isn't a 'watch' folder type feature built in. You might check out http://dougscripts.com/itunes/ for some possible work arounds, though. If there's a script for it, that site will have it. - Bob M. Montgomery from twhirl

Also, as a side note, you can sync itunes and wmp/mce with music bridge, which can also be run w/a gui and from the command line. I manage all of my music with iTunes, and then have a batch that copies/updates it across the network to my VMC, which then updates it in iTunes, and then syncs the meta with wmp/mce... nightly. - Joel Tanner

Joel, great tip! Thanks. - Bob M. Montgomery from twhirl

Using iTunes to rip CDs is what I do.... works great if you have it auto-rip on insert, and then auto-eject when complete. But... there are many times when I'll be on another computer and rip something, and then it needs importing. Also, for those who download music... iTLU can help automate the process, as I mentioned. - Joel Tanner

Have you tried Media Monkey? - Alastair Montgomery

Media Monkey only monitors folders if you go for the Gold $39.95 version though. - Joel Tanner

thanks guys, it sounds like this is indeed a limitation of iTunes. WMP can monitor folders which I really liked but lately has stopped being useable so I've had to switch to iTunes. Will check out iTunes Library Updater (thanks Joel). Still haven't tried Media Monkey yet Alastair, need to do that at some point. - Thomas Hawk

iTunes isn't really a music manager, it's just a front end to a store. It's design princilpes aren't focussed on helping you, they are focussed on selling you stuff. - Rich

Adrian the problem with ripping the CDs in iTunes is that I want to later move the music and put it in a hierarchical music file folder structure I've made alphabetically on an external drobo. I'm going to start trying to rip with iTunes (since WMP won't pull up meta data from the web when I try to rip a disc with it) but I'll need to move the music after I rip it. - Thomas Hawk

Thomas, what sort of directory structure are you using? And how many tracks are you currently managing? - Joel Tanner

Another one on my list to try is SongBird, don't know if it monitors folders though. - Alastair Montgomery

My library is over 50,000 tracks, and nearing 300 Gb.... and as Oliver suggested, I let iTunes manage he directory structure and file naming -- although it took me awhile to trust iTunes to do this. - Joel Tanner

The Zune player does it -- WMP should be able to do it - Shey

That puts my 22Gb library to shame :S - Alastair Montgomery

I have an addiction to music, and building my library.... - Joel Tanner

after A LOT of trial and error, and testing, I've come to the conclusion that iTunes does a farrrrr better job of managing files based on meta than WMP does. This is also why I use Music Bridge to sync meta from iTunes to WMP/MCE so it's much cleaner and more organized when I pull up music in Media Center - Joel Tanner

The problem is as a Windows app, itunes sucks. Try the Zune software, it isnt tied to a zune player, manages music really well, monitors folders and does a good job ripping CD's. - Soulhuntre from twhirl

Soulhuntre, why do you think iTunes sucks on Windows? it's nearly identical on OS X. - Joel Tanner

helpful thread. I use a Mac.. but still interesting. why isn't winamp a standard anymore? - NoahDavidSimon

re: winamp .... ever since AOL took it over it went downhill and lost marketshare (does it even have any now?), and then of course iTunes removed most people's need for it. - Joel Tanner

I still have version 3 on my laptop at home, just for its small footprint. - Alastair Montgomery

Check out what definitive Paul Thurott has to say on this music/server subject. He rips his entire collection to both MS & Apple. Also look at WHS (Windows Home Server). Still in infancy, and typical MS project "You buy it, you fix it.", but the HP version has excellent iTune server synch. WHS slowly becomes a "must" for photographers, along with superb Mozy. - Douglas Hopkins

Adrian, I've never noticed playback quality issues on iTunes on my end. What sort of comparison have you done between the two, and any reason you think there is a difference? - Joel Tanner

Joel, I'm managing about 120,000 mp3s at present. It's a very large library and although WMP in Vista is much better in terms of not making me wait 6 minutes to hear a song, lately the WMP library is constantly corrupting. It won't recognize discs anymore, won't write ratings of songs to files, only includes 2,000 of my 11,000 5 star songs in an auto 5 star playlist, etc. - Thomas Hawk

the only solution when I have these WMP problems is too nuke the "corrupted" library and reimport it which can take days. Even then very quickly the same problems crop up. iTunes took a long, long time (like 5 days) to import my library but now seems to handle it much better than WMP did. - Thomas Hawk

Winamp was only crap when AOL first took it over. It's as good now or better than it ever was. If youv'e not tried it since it sucked (briefly), you should try it again. - abacab

Thomas, holy crap. I knew you had more than I (from a discussion a long time ago), but my gawd that's insane. I have noticed that Vistas WMP is much better on memory/processor, but it's still put to to shame by iTunes with my collection. I'd be VERY curious to know how your collection fares with iTunes. Also, what are the specs of the machine you're managing your music on? - Joel Tanner

Adrian, did you have custom equalizer settings in Winamp? - Joel Tanner

Many people I know agree that Winamp is the better player, but it lacks in managing your music library. - Amit Morson

Why the switch? - Sean Alexander

Thanks for suggesting iTLU. - Remo

No problem. iTLU has been a life saver for me. The apps got a lot of great features for not only adding new tracks, but also cleaning up your itunes DB. - Joel Tanner from IM

Adrian: re: musikCube... I was (and am, still) a long-time user. Great library management, great player, and really great audio. Not really a ripper, but a great app for the price otherwise. Super-large libraries can bog mC down, but that happens with any audio library tool/player/util. I'd love to see mC make a real comeback. - abacab