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OSX Makes Me Feel Really Stupid .:.

Here at the Brewstead we strive to be platform-agnostic. We have two aging Windows desktops, three machines running Ubuntu, an iMac, a G4 laptop, and a FreeBSD server in the closet running the mail and doing network backups. Most of our stuff works, most of the time, which is about as good as it gets.


Every time I have to do something on a Macintosh that does not involve running a canned program, I feel like I've had a stroke, or one of my arms has fallen off, or I've experienced sudden, disastrous macular degeneration. Without warning to my long-suffering family, I turn into a cranky, swearing, chair-throwing moron.

Case in point: the time I wanted to grab my stepdaughter's 900-song iTunes library and move it from her iMac (which was running Tiger) over to her brand-new Compaq off-to-college-in-the-fall laptop.

That time, I wrote it down. Return with me now to days of yore, when everything happened in the present tense....


As with previous adventures in OSX--see "In Which I Fail Miserably In My Attempt to Share a Windows Printer with OSX" and "In Which I Fail Miserably In My Attempt to Copy Files from OSX to Anything On the Network"--I am feeling very cranky and stupid right now.

Here's the deal. Most of Allie's songs are imports from her CD collection and can't be reinstalled from iTunes. I'm looking for a quick easy way to export these songs so she doesn't have to suck 'em all down again from the original disks.

First, I try burning them to DVD. Ah, what a comedy of errors. I can't figure out how to get the DVD to show up anywhere on the system, for starters. Turns out I need to go into system preferences and re-rig the default behavior when the blank DVD is inserted, and then "name" the DVD, and then go through a completely random set of actions ("Finder," "Disk Utility") before anything appears on my desktop suggesting that a blank DVD is actually in the drive. This takes a mind-numbing amount of time to figure out, maybe a half-hour or more, mostly because I lack the vocabulary to phrase the question in such a way that makes sense to the help program or the Internet.

Then I start dragging things in from iTunes, which is problematic: try to drag too many files (over about 60) and Allie's poor little iMac will randomly hang. Several abortive attempts later (this takes at least another hour) I have all the files dragged over to the DVD.

Sweet, I think, clicking into the DVD to check files ... and ... arrgh. No. Only about 400 of the 900 files are there. I can't tell which are missing, because the file names are not the same as the song titles, which are all I could see in iTunes.

Next thought: "Okay, screw it, let's just burn that sucker and go to bed." Um. Hmmm. How exactly do you burn a DVD with MacOS? Shouldn't there be, um, something? A button? There's nothing, just that blank-faced icon, mocking me with its simplicity. ("It's so simple," whispers the icon. "But you can't figure it out, so you're a moron.")

Off to Help I go again, feeling stupider and stupider, and Help is singularly unhelpful. Off to the Web, which is opaque: apparently this is something that everybody knows how to do: they just say "burn the DVD."

And then, finally, I find it. To burn a DVD on MacOSX, you drag files to the DVD, and then drag the freaking DVD into the freaking trash. (Why, God, why????)

So I do this ... and the drive starts humming to itself in a promising major key ... and it's now 1am, and I'm sick, so I go to bed.

In the morning, I get up, and there's nothing on the screen. No success message, no error, the disk hasn't popped out, and there's nothing to indicate a DVD was written. So I pop the thing out, look at it, and there are writing-tracks on the DVD. I plug this into Allie's new laptop, and nawp, there's nothing on it, as far as Windows is concerned.

Neeeeeat. What a giant waste of time. (I cannot wait to take a sledgehammer to this thing; I've got the Geto Boys' "Still" cued up on my $40 non-iPod MP3 player, which by the way works like this: I plug it into a USB port, drag files onto it, and I'm done.)

Before heading off to work I try installing a drag-and-drop SSH client called Fugu. This kinda-sorta works; I can log onto any of several handy Unix accounts and create directories just fine, but when I try copying a file, it hangs about 90% through. Doesn't matter which file; the same thing happens with music and with text. Sigh.


Days later: no useful help from any quarter. Made another attempt to burn the DVD, which failed again. Wound up going to Fry's, investing $50 in a 2-gig thumb drive, and moving all that music over in three trips across the good old sneaker network.

And then I had to figure out what to do with Allie's spanking-new iPod, which needed to be reformatted before it would talk to her PC, even though it was stuffed with songs from her dad's collection. To make a long story slightly less long, it turned out that a Mac-formatted iPod won't talk to a PC, but a PC-formatted iPod will talk to a Mac.

Funny thing: I also sense the same attitude in people, which seems more than just a tad ironic.

Comments from before Disqus:

Terry Riegel .:. 2010-04-07 12:35:12
For me I usually just copy the complete iTunes folder from one machine to the other.
Jeff E Mandel MD MS .:. 2008-01-01 11:26:43
Sorry it is so confusing for you. Since Ryan has an iPod now, and suggests that you will try to sync it to his Ubuntu desktop, here are some suggestions:

1) sudo apt-get install netatalk
If you want it to do fancy things like support more secure authentication, read the FAQs. Having a network mountable volume makes it much easier to deal with all things Mac.
2) sudo apt-get install mt-daapd
This gives you an iTunes server on your network, which permits iTunes from either platform to see the music you copied to the network share. Not a complete solution, as you can't sync libraries, but ou at least have access.
3) If you intend to manage the iPod from Ubuntu, you should be done; if you want to manage it from iTunes Windows via WINE or Crossover, this will be more painful, but doable. From a Mac client, it is possible to import a library with 3rd party tools, but if you have a Mac and no particular need to sync multiple libraries, it is easier to just leave all the music on the Mac.
4) If you have other devices such as the Squeezebox on the network, it is possible to install the squeezeserver on Ubuntu, but there are some issues with Perl that require careful reading of the HOWTOs and editing of apt.sources to get the proper libraries installed.
5) It is possible to mount an iPod as a USB device and copy files to it, but this assumes you know which of the 10,000 files named SONG.MP3 is the one you want. All iTunes is doing is organizing your files hierarchically and putting the metadata in an XML file; you can always ssh to the box and scp the file if that's what you want to do.
6) Allie's old iMac is USB 1.1; new iPods are USB 2, and tend not to pair well.

Good luck.

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