iTunes Windows/Mac interoperability issue

Howdy from Fort Worth TX,

I have an iTunes interoperability issue that I’ll outline as follows:

For awhile I’ve been trying to implement a basic music server system. I have a Dell Inspiron (Windows Vista SP1), to which I’ve added an extra internal HDD (NTFS, 320GB, which I call G:), where my audio is stored, mostly in Apple Lossless (ALAC). I also have a iBook G4 which runs 10.4.11, which AFAIK is the latest pre-Intel and pre-Leopards Tiger OS.

I’m using iTunes client software mainly because of its ubiquity; I haven’t as of yet played with any hi-res files, which would require other software clients anyway. My goal in all this is to eliminate the CD player from my stereos, building them around the music server and an Internet connection, and having LP playback in the main system. At that point, I would only use the silver disc for archiving.

The SMB client in the iBook’s MacOS works like a charm. From the iBook, I can login to G: either from Finder or from within iTunes itself. I can also rip from or burn to either of my computers’ optical drives, and get a respectable ~10-20x speed across the network on my iBook. I’ve even done simultaneous rips, simultaneous burns, and burned on one and ripped from the other. So my network works.

Now for the problem. From either system, sometimes I can’t find some of the files. Sometimes it’s entire albums; sometimes it’s certain songs within an album. This is denoted using an exclamation point icon next to the index number of the file on the iTunes desktop. If I click on the file, it gives me a dialog box to locate it. Then I have to drill down to find the files. I have to do this for each file, one at a time. Alternately, I can drill down G: (from WinEx or Finder) and do a drag-and-drop of the offending file or folder to the iTunes desktop. This creates duplicate aliases, which I must then remove manually.

When I’m on the Dell and I try to sync the files with it, then my Mac can’t find them, and vice versa. But by analyzing the metadata (Artist, Album, Name), I think I’ve isolated the bug to the Windows version of iTunes.

I don’t know much about iTunes, but apparently it consists of the GUI, a Library file which holds and organizes the metadata, an XML file which populates the GUI with the metadata, and, of course, a media player. As well, it includes an ebusiness client that’s the whole reason for its existence, but I won’t get into that.

Contemporary versions of Windows can accommodate foldernames and filenames of 256 bytes, certain characters excepted. But iTunes for Windows, for some reason, truncates these names to 40 bytes. This can be a real problem, especially in the classical repertoire, where wordy descriptions (say, artist credits or symphonic movements) are often the norm. Also, the Gracenote CDDB used by iTunes may have names with characters that the Windows version doesn’t allow in its syntax. The MacOS with its UNIX-derived kernel is more permissive.

Whether one uses Windows or a Mac, the metadata is parsed, string-literally, into the iTunes library. Either version creates an alias on the desktop, which allows it to find and process the file. On a Mac, the alias and the target names match; on Windows, due to the field size limitations and input masking, they don’t. That seems to be the reason I have to resync back and forth. One would probably never have this issue with just Windows boxes or just Macs.

So, if I haven’t bored y’all with the above, what I’m looking for is a workaround that would allow more interoperability. Winamp may be an option for the Dell, as AFAIK it now supports Apple Lossless. Also I understand that the payware version can support hi-res (>44.1/16) files. RealPlayer can be run across both platforms, but I don’t know if it supports ALAC. But I’d rather stay with iTunes on both machines at least for now, and I don’t know whether or not implementing either non-iTunes client on the Windows machine would solve the naming or location issues.

Also, looking for a workaround to the much-maligned CDDB issue parsing classical metadata, but I’ll save that for another post.

Thanks, John
Hmm, I feel your pain. I personally hate iTunes because of it's bizarre file-management methods. I use a Windows machine to rip CD's and put it on my Linux server (and some of these files have very long names), and programmatically create MP3 equivalents of the FLAC files on my Linux Server that my Mac accesses via iTunes. (The original FLAC files are used by the Squeezebox Server on Linux.) Talk about multi-platform!

The exclamation marks come up frequently for me. I've never figured out exactly why, but I have read about a workaround: Hold the SHIFT and OPTION keys when you're opening iTunes, and choose your regular iTunes library.

How would things work for you if you used the Mac as the server for the PC? Does iTunes still truncate the filenames stored on a remote machine? That's bizarre behavior to truncate files after 40 characters -- my Mac version of iTunes doesn't seem to do that.

Whew John . . . I think you're stumbling onto a good handful of issues that can make file-based music organization really frustrating. My knowledge on the subject is pretty limited, so I'm just sharing some musings here . . .

First, on filenames -- I ran a business for several years that used both Macs and PCs sharing files located on a Sun UNIX-based server, and found that the only way to have consistent intercompatibilty was to make sure that the filenames were ALWAYS in a format that was natively compatible with all of the OSs. So you may need to use a utility to re-copy your entire library and re-create filenames (from the tag info) into an abbreviated format, while leaving the tags alone for organization.

Second, I've also had weird network-sharing issues that are related to antivirus software on both Windows client machines as well as a Windows 2003 server, and since your server is a Windows machine you might see if temporality turning off any anti-virus apps helps the issue.

Third, you might consider the manner by which the shares are set up and named -- from what I understand the Windows friendly-name system (NetBios?) doesn't have consistent support in other environments, so you might try setting up a fixed IP table and mapping any network drives with the IP address.

And then there's the whole fact that there exists no system using standardized tags that really works for a classical collection . . . The only thing I've found that's really better is the Kaleidescape system, and it's multiple-platform synchronization with Kaleidescape Conductor. Truly clean, good metadata support done automatically, as well as excellent cross-album composer sorting, in addition to notes and performance details from All Music Guide. And outstanding sound quality (especially with outboard DACs) but no high-res support, and none planned in the near future.
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I'm not sure what you are trying to do. Are you just wanting to be able to play the files from either machine? If so why not maintain the database on one machine and have the other machine share it via the iTunes share function?

BTW iTunes can handle Hirez files.

I was/am under the impression that a outboard hard drive has to be formatted for a Mac.
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Windows latest format = NFTS
Windows old format = FAT32

Windows can read/write/format both but can't read/write/format any mac formats

Mac can read but not write or format NFTS, can read/write/format FAT32 so this is the one to choose when sharing between mac and PC if the drive is connected directly via USB or Firewire

As Shadorne says, either can use a network drive.
Howdy again; thanks for all the responses.

Per Shadorne's post, I've been using the Mac as reference for some time now. I've figured that was the best way to go, since I can move the iBook from one stereo to the other. The Dell is in my home office, and only drives powered speakers, so no big deal if I can't access my whole library from there.

Before I added a second HDD to the Dell, I had a LaCie 250GB piggybacked onto the Dell using Firewire. The LaCie was formatted to FAT32. But it trashed after only 2 years of use, so I bought the other HDD and put it into the Dell. That HDD is a WD. And yes, I had to rerip my library; that was painful to say the least. At present I have only 100GB or so done. Anyway, I can only format the WD to NTFS (AFAIK you need an aftermarket plugin to get FAT32). In any event, I had the same compatibility issues with the LaCie, so it's not a FAT32 vs. NTFS issue.

Kirkus seems to suggest some plug-in which may rename files to some lowest-common-denominator syntax, but I don't know of any. Also, Herman suggested sharing the libraries. I tried enabling Home Sharing on one machine, then the other, then both, but in no case could I see the other library from either desktop. Apparently, Home Sharing uses some very basic protocol that may be something like Windows' NetBEUI, but can't communicate across platforms. So I turned Home Sharing off, then turned NetBEUI off on the Dell and AppleTalk off on the Mac, enabling only TCP/IP on either. Same problem.

Then, I turned off DHCP at the router and setup static IP's for the Dell and the Mac (192.168.x.x). Same problem. So I think I can conclude that it's not a networking issue.

Again, I think the bug is within the Windows version of iTunes, so even if I upgrade to a NAS, I don't think that'll fix it either, since the NAS will have to be either NTFS or FAT32, not Mac, and AFAIK it appears to be iTunes for Windows, not Windows itself, that seems to be doing this file renaming. I think I'll do NAS in the near future though, even though I'll need to get another router or switch (right now, I'm moving my iBook between two stereos and my kitchen and using using the Dell in my home office; that makes four points, which is the number of ports my router has). And, NAS will give me the advantages of RAID.

Over the next few days, I'll try to locate or rip a difficult file (like a classical movement with a long name and special characters) from the PC (to duplicate the issue) and post the file's FQPN and nomenclature (as seen from either platform) to the group so everyone can see the issue. In the meantime, thanks to all of you for your help and comments.

All the best, John

The LaCie was formatted to FAT32. But it trashed after only 2 years of use

Not really all that bad. The basic rule is you have multiple backups and expect any drive can fail at any time.

It can indeed share across platforms. I share your pain but it seems you have so many issues that your situation may be unique and so complicated to the point you may be on your own. When you post a 12 paragraph problem it would be amazing to get your issue resolved in one thread.

Good luck!

John... I'm using a Seagate Black Armor NAS drive for my music file storage (about 40,000 tracks). It works well on the wireless network and several PC's, I don't use MAC's but my iPhone will access it. However it should work with any computer. I believe the OS of the drive is UNIX, since they give you software to run on both PC's and MAC's so they see it on the network.
Thanks for y'all's interest and patience with my windy problem description. Talked to my Apple tech re this; he concurs that the root cause lies within iTunes for Windows. Also talked to two Geniuses, one of whom had actually encountered a similar issue. Ditto.

Also, all three agreed that the Home Sharing within iTunes works best with WinXP or newer, and Intel Macs. My Mac is a G4.

All in all, though, this project has failed to banish the CD player from my stereo. CD's coax out is still better than computer's USB out through the same DAC. Right now, with USB audio in its infancy, I just can't see throwing big bucks at a USB DAC if IMHO it's probably going to be a paperweight two years from now.

In the meantime, I'll save my nickels and dimes for my last CD player. How many times have you heard that?

Thanks again and all the best, John
Thanks again for all your posts. Just two more ?'s for the forum, one slightly off-topic.
First, in the "As We See It" article in August 2010 Stereophile, John Marks alludes to iTunes having 24/96 capability. I only see 24/48 (from Audio MIDI Setup) on my installation. Is this an aftermarket plugin, or perhaps only available on G5 (Intel) Macs? Or, perhaps 24/96 requires more RAM than the 1GB I have to handle the denser datastream. OS is 10.4.11; iTunes 9.2 (61).
Second, and slightly off-topic, any word of a dock for the iPad that has Ethernet connectivity? Since 802.11x sits on Ethernet--and is native to the iPod touch kernel, upon which the iPad is based--that should be a fairly easy thing to do. Such a dock should also have some way to get at the digital data to feed a DAC, such as a coax or USB-A out. Really, if I had a factory in China in my back pocket, this would be an easy build. A little weight on the bottom of the dock to balance the iPad, the requisite connectivity on the back of the dock, and voila--a poor man's Sooloos for the rest of us!!
Correction to my last post--Audio MIDI Setup lets me choose only between 16/44.1 (Red Book) and 16/48, not 24/48. Connected DAC (via USB) is a Musical Fidelity V-DAC, which, according to specs, upsamples to 24/192, so it's not a DAC issue. I selected 16/48; most of my stuff is RedBook in Apple Lossless, which AFAIK the iTunes client downsamples to 16/44.1. I'll check with my Apple tech to see if it's a memory issue. Thanks again, John
The mac is pretty smart and should display all rates the attached device is capable of processing. Just because the dac upsamples to 24/192 does not mean it will accept 24/192 data.

The manual for the DAC doesn't anything about it though. MF should be able to tell you.

I would set A-M to 16/44.1 and let the DAC upsample but try it both ways to see if one sounds better. If you select 16/48 then it gets resampled twice, once by iTunes to 16/48 and then again by the DAC to 24/192.

One of the nice things about Audio MIDI Setup is that you can set sampling rates on the fly. I tried 16/44.1 (the default), then 16/48. To my surprise, 16/48 is better, and the difference is NOT subtle.
That's not exactly correct.

iTunes locks onto whatever AM is set to when it launches and outputs that until you relaunch it with AM set to something else.

If you launch iTunes when AM is set to 16/44.1 then iTunes will output everything at 16/44.1 and your DAC resamples to 24/192.. if a file is not not native 16/44.1 iTunes resamples it to that.

If you change AM to 16/48 without relaunching iTunes then iTunes still outputs 16/44.1 and AM resamples it to 16/48 and your DAC resamples it to 24/192. That should sound worse but if it sounds good to you then it is good.