iOS 7 and iTunes 10

Dear Lazyweb:

Am I correct in assuming that if I upgrade my phone to iOS 7, it will demand that I upgrade my desktop to iTunes 11 in order to sync my music or do a local, non-iCloud backup?

I'm still running iTunes 10.7 on MacOS 10.8 because iTunes 11 deleted features I depend heavily upon. I suspect that my unwillingness to upgrade my primary machine to iTunes 11 means that I can't ever upgrade my phone again, but I'd like confirmation of that.

Update: Are you surprised that the answer is "yes"? I am not surprised.

Tags: , , , ,

49 Responses:

  1. Patrick says:

    Yes, if you ever want USB syncing ever again. That said, supposedly you can live a mostly happy life without syncing your iOS device back to your desktop. I dunno if the wireless sync breaks enough that iTunes 10.7 won't talk to iOS7, though.

    You could also probably get away with a 10.8 VM running iTunes 11.1 for iOS Device Purposes these days, I think? I seem to remember Apple getting less draconian about virtualization in the latest release, but I haven't tried. VMWare seems to think it's doable, anyway. VirtualBox hits are polluted by non-OSX hosts having to hackintosh the guests, but I'd guess you'd need to convert the ML installer appbundle into a bootable image and point VirtualBox at it on an OSX host.

    • jwz says:

      I don't do iCloud backups because I'm one of those tinfoil hat security hardasses who doesn't want Apple to have a copy of all of my passwords.

      The VM thing sounds like way too much work.

      • Patrick says:

        Ah, I don't think iCloud backups have passwords in them? You have to jump through extra special hoops to even get those in local backups - the "Encrypt iPhone backup" option is necessary to capture password details. Setting an iOS device up after restoring it is a weeks-long adventure of discovering the invalidated authentication tokens all over again. I suspect iCloud backup really only backs up the current installed application list, screen layouts, preferences, photos and account information without the passwords. Media will resync from the local iTunes and contacts and calendars come from the cloud and voila: Your iOS device freshly scrubbed and new! cough

        But none of that is actual proof that the transmitted data doesn't have some accidental leak. I can respect that.

        And yeah, OSX VMs are waaay too special snowflakey to bother with unless if you have a developery type need for multiple dev tool revisions, and even that is.. There's gotta be a better way.

    • Ry Jones says:

      iTunes 11 is also a requirement for wireless syncing with iOS 7, sadly.

      Your whole vm story is confused. You could use Parallels to install from your restore partition, then install iTunes 10.7 within and never update it, but my guess is the end of the story is keeping things as-is.

      I have not tested sharing a library between 10.7 and 11.1 (or whatever came out today), but I'm sure it requires fuckery.

      • Patrick says:

        Really? Damn shame about that.

        But I guess the confusing part was that VMWare knows how to convert the "Install OSX Mountain Lion" app into a bootable OSX Mountain Lion guest partition without any manual intervention. You just tell it to use the app as a bootable installer and it figures out how to get there. Half an hour later you have a bootable 10.8.0 guest running iTunes 10.old.

        But Fusion is a $70 product compared to a free VirtualBox host, and VirtualBox doesn't know the secret to make the app into a bootable image. And while you could _probably_ share ~/Music across host and guest, it would be continually janky. Probably way more trouble than it's worth aside from as a curiosity.

        • grェ says:

          So, because you mentioned virtualization as an approach/solution to this (and I'm fond of virtualization for various reasons).

          Virtualbox should not be used to host OS X. Honestly, if you care about things, it shouldn't be used to host anything. The workarounds to get OS X working within Virtualbox will take you more time than buying Parallels or VMWare Fusion; and if you're like most people who can afford a computer, you probably get paid by the hour or something roughly equivalent. Is your time really worth so little that wasting hours of your life just so you don't spend $40-$70 (depending on coupons/discounts/etc.) in software could by you?

          Well, if so, then there's a better virtualization project that needs your help: bhyve! It's the most nascent of all virtualization systems, isn't even 'out' in an official form (though it runs on recent versions of FreeBSD and is part of the 10/Current branch if you want to grab a snapshot to use with it). That said, if, like me, you are into said project; you may be thinking "hey! I'll just nest that in a Virtualbox VM on my OS X host!" but then you would also be sad, because you'll realize that Virtualbox doesn't properly pass the VTd/VMX instructions required for bhyve (it is after all, very minimalistic, and really only useful on very modern amd64 and Ex64T hardware; you may even be thinking 'wtf is this bollocks? I bet they just want me to buy new hardware!' and you may be right, but then, most software is written this way these days).

          You may want then want to say "grumble, fine! No Virtualbox! But I'm still sick of VMWare, those guys get so much of my money already! Give me Parallels!" But then you'll realize that Parallels also doesn't support VTd/VMX for guests properly. ;_; You will eventually give up, shell out $40-$70 for VMWare fusion; all esoteric nested virtualization problems will go away, and you can focus on the bugs in the software that you're actually trying to get working, instead of the system in which you're trying to get said software running in.

          So yeah, as someone who spent the time; sometimes implementations matter. VirtualBox is not one I would give any time or money to. Parallels, I sadly gave both towards. VMWare Fusion I've given both towards.

          bhyve well, that's just tons of time.

          But if you want free (as in GPL) virtualization, use kvm, or qemu, or whatever else already.

          But good luck nesting OS X in those, good luck.

  2. cowmix says:

    Get the cheeeeapest Mac you can find that can run iTunes 11.

    Done and done.

    • phuzz says:

      Isn't 'cheap' a relative term when you're talking about Apple products?

      • cowmix says:

        I meant get some junker off of Craigslist.

        My home automation software required OSX and that's exactly what I did.

        • phuzz says:

          That's a much better idea. How does licensing work with OSX? Can you just install a newer version on any old hardware? I don't remember it ever asking for a key, so do they track installs in any way?

          • cowmix says:

            Worst case it is $30 but Apple is pretty lax about checking on that stuff.

          • Tim says:

            The only known copy protection mechanism in OS X is aimed at people who want to use OS X without paying for Apple hardware. A few important system binaries are encrypted. To decrypt them, the loader needs to be able to read a decryption key stored in hardware built into a real Mac's motherboard.

            None of this is hard to work around, which is why Hackintoshers are able to do their thing. The generally accepted theory is that it's a token system to give them DMCA leverage for suing commercial operations which try to sell Hackintoshes, and they seem to have an unofficial policy of not going after individuals. (Under the DMCA, circumventing a copy protection device is a no-no.)

            They don't track installs since there is no individualized license key. Also, as of the versions you buy from the Mac App Store (10.7 and 10.8, soon 10.9), buying it once grants a license to install and run it on up to 5 computers you own, just like other Mac App Store purchases.

            • grェ says:

              Yeah, with non-Beta Lion/ML, they definitely track installs via App Store. This is even true for systems installed via OS X Server's Netinstall functionality. The 'recovery mode' partition will even try to phone home and check for eligibility if there's a working network connection and bitch at you if there isn't (but it may still work; conditions seem fickle).

              I would guess running the windows version of iTunes under WINE (or the earlier vilified Virtualbox to host a windows or perhaps even ReactOS guest) may work if you wanted to run two versions of iTunes. Maybe? No idea. Sounds like a hassle.

  3. Line Noise says:

    Remember back in the day when Microsoft had an anti-trust suit filed against it because it tied a web browser into its operating system?

    Who in their right mind would think that tying a music player into their operating system is a good idea? Oh, right, Apple.

    • antabakayt says:

      Fun thing: If you are running MacOS, you may have to update your Safari browser after you updated iTunes. Happened to my wife. She has since changed her mind about Apple being awesome. Next computer will be a standard PC again. Which is fine by me, because I absolutely loathed doing customer support on her PowerBook (I don't use MacOS myself and told her upfront I wouldn't be able to help her, but did she listen?).

      There is just no anti-trust suit against Apple about this because they still have a comparatively minimal market share in the PC-OS area, so nobody cares enough.

      • antabakayt says:

        Addendum: Btw, that iTunes version back then (needed to activate your iPod2) worked fine with WinXP (from 2002) but would not work with any MacOS before 2005 (and you needed a specific Safari browser version). That's even worse deep integration than what MS ever did.

        • Tim says:

          It's a consequence of (a) splitting out the actual HTML/JS code into a systemwide shared library called WebKit, and (b) proceeding to WebKit in a lot more apps than just the browser because it's so damn useful.

          iTunes uses it because of the iTunes Store. Ever browsed through it? You're really looking at a WebKit view which is showing you HTML served up by an Apple server. Same goes for standard OS X help, it's all HTML.

          You're fighting a really old battle that turns out to have been a bit misguided. Everybody does this now because it actually makes a lot of sense to have a standard HTML rendering library available to any app that wants it.

          • antabakayt says:

            Yep, that explanation makes a lot of sense and is still completely infuriating, since iTunes on Windows works fine without a similar Browser integration. Even Microsoft never integrated their stuff that deeply (they just claimed they did, but actually it was quite easy - as demonstrated - to remove IE).

            • cthulhu says:

              Read Tim's response again - it's not a browser integration; it's that both iTunes and Safari use HTML/JS, which is handled by a separate WebKit library. My unverified suspicion is that since iTunes on Windows can't rely on this system WebKit library, iTunes on Windows is more-or-less self-contained.

              • antabakayt says:

                Yes, I got that and thanks for repeating my point.
                iTunes on Windows: Self-contained, no deep integration with shared OS resources supplied by other application.
                iTunes on MacOS: Deep integration with shared OS resources supplied by other application, forcing you to upgrade two applications.

                • grェ says:

                  I have observed this sort of thing seems to vary by version.

                  There were periods where OS X required reboots after updating Safari, again due to tightly coupled webkit integration. Then they managed to realize that was stupid and did away with it at some point it seems. I imagine the coupling between iTunes and Safari may be similar. I would not count on it being strongly coupled; it seems to be Apple's general design trend to reduce the number of things that require reboots after updates, not increase them.

                  If you're still harping on Apple for such slights compared to their commercial competitors in 2013; I pity you. And if you think that Windows Update is even remotely as sane, I think you've probably never been paid to have to manage deployments for hundreds or thousands of windows systems. ;_;

                  If you're dorking out with some linux distribution, wake me up with apt/rpm/portage/etc. don't exhibit similar issues, but you don't mind because you feel it gives you geek creds for fixing things when they break. I think your wife was probably sane; and if she hasn't been asking you for tech support until that (and if that, why?) then she probably doesn't need your misguided perspectives on tech anyway. ;)

    • Back in 1995 I bought a PC from a small family store in Perth, Australia. The list price included Windows 95. I was going to install Linux anyway, so I asked how much less it would be without Windows. Their answer, “It doesn't make a difference.”

      Turns out back in the 80s, Microsoft went to every PC OEM and said, "You can pay us $50 per DOS license, or you can pay us $10 for every PC you sell no matter what OS you put on it." As a result every PC you bought came with DOS (and then Windows 3, and then Win95) whether you wanted it to or not. And even if you said you didn't want it, you'd paid for it. The incentive for OEMs to even _suggest_ there might be alternatives to Microsoft was zero.

      I mention this only because I get annoyed when people propagate the idea that bundling a browser with a majority-share OS was the sole sufficient condition of their antitrust violation. Fucking Netscape with a zero-cost, bundled browser was only possible because Microsoft had already fucked the rest of the industry just as hard.

  4. chris says:

    You think you've got problems. I sync my phone with a G4 powerbook that doesn't believe in itunes past 10.6.3.

  5. Mike Shaver says:

    iCloud backups have the keychain, but they're (the only part that is) encrypted with a device-side key (the 0x835 on-chip one). I don't think it's known if Apple "escrows" those keys somehow for LEA, or if they can then map from device to key based on information in the iCloud data.

    There's a good CanSecWest presentation on this stuff somewhere, from an Elcomsoft guy.

  6. There was a time when apple was good, but they've gone more evil basically since iphone. It's gone to their heads a bit...hold back features to push future sales etc.

    when I got my '4' I had to upgrade my entire MacOS, then still upgrade itunes...for the privilege...

    And i agree totally that they've been making itunes worse and worse. It reminds me of the Small-Midsize truck. At first it was a pure, clean answer to a basic need. By today it just doesn't exist.

    Maybe the grass is greener elsewhere...maybe the best upgrade is a new OS. Do you have much interest in android, etc?

  7. tl;dr some iTunes 11 pet peeves have been fixed. Mostly usable now. Mostly.

    I put off installing iTunes 11 for almost a year because it just looked horrible back when it was first released. Font changed, no album artwork in songs view, no iTunes DJ. I even restored my Mac from backup to get iTunes 10 back.

    It dawned on me I was going to have to bite the bullet and upgrade iTunes after I finished the iOS 7 upgrade yesterday. Ugh. Default font still horrible, but easy enough to change it back to LucidaGrande, and they fixed album artwork in songs view. So two major things I hated about iTunes 11 are no longer issues.

    "Up Next" still not iTunes DJ but you can have it play smart playlists either by dragging the playlist to the window bar, or clicking the shuffle icon in the track listing area. So, it's kinda/sorta similar? Miss being able to see what's, er, up next in the main track listing area instead of that small popup window mind you.

  8. Kevin Binswanger says:

    Not just iTunes 11, but 11.1. At the time iOS 7 dropped, this version of iTunes was not available for my system (64bit Windows). So iTunes reported, "We can't sync without version 11.1, go here to install it", and the install link only had 11.0.x.

  9. owen says:

    If you cough up the $25 a year for iTunes match (which iTunes 10 supports) you get over the air automatic sync - plus you can stream music from your collection over wifi/LTE without having to have it synced to the iPhone. I think this is the most undersold/underrated feature of iTunes, and it's a lot cheaper than the suggested "buy a the crappiest machine you can find just to install iTunes 11 on". Worth it. (And if you try it and don't like it, bug apple support for your money back)

    • jwz says:

      Fuck that. My music exists in files. I wish to merely transfer those files between two devices in my physical possession.

      Next person who suggests "pay even more money for some halfassed workaround that doesn't actually solve the problem as stated" gets banned.

      • Owen says:

        As far as i know match actually puts your files in the cloud where your phone can get them. So it is in effect putting files on device in a way that may work. But. It seems that it uses a mix of [REDACTED], which breaks your no-msft-software rule. So. I find your reasoning flawed, but the agree with your not accepting this solution. I hereby withdraw my suggestion.

        • jwz says:

          You seem to think that "the cloud" and "files on devices in my physical possession" have something to do with each other. Fascinating.

          BTW, "the cloud" is what we used to call "the Internet". Why do you think it needed to be renamed?

          • Owen says:

            Noted and understood. Re:"cloud", Not me that did the renaming in this instance, I don't like the term. Blame Amazon and Microsoft.

          • Adolf Osborne says:

            Every time someone mentions "the cloud" as a solution to [insert problem], picture that someone as one individual in a sea of strange, little green three-eyed men and think of this:

    • Owen W. says:

      This is the worst possible idea. "Apple is screwing me over, why don't I just hand over even more control of my data to them." You're a disgrace to the name.

      • Owen says:

        Heh. Problem: syncing iTunes 10.7 and ios7. Gave a solution. Realized not acceptable afterwards and withdrew suggestion.

        And re: our name, I blame the parents.

  10. sherm says:

    I get your OS X vs Linux reasoning on the desktop but does it really apply to smartphones at this point? I still prefer and use an iPhone, but I'm apparently more desensitized to Apple's "Oh, you used that feature? Fuck you, you'll buy it anyway" product management than you are (plus I don't run DNA Pizza).

    Every Android-based phone I'm aware of lets you mount the thing to your Mac as a USB storage device and drag your music files over in Finder (or, heaven forbid put it on an SD card), no sync bullshit.

    • jwz says:

      The reason I'm not using Android is because I find Android's UI to be a laughable piece of shit. Basically, Android feels to me like what happens when Linux developers try to make a phone. Which, in fact, it is.

      • I have no dog in this fight and I really hope you don't take this to mean that I'm proselytizing. I switched from the 64gb Iphone to the Google version of the Galaxy s4 recently. Stock Androids polish is on par with IOS. Earlier versions were terrible but they have iterated quickly and having a focus on UI coherence and polish in recent versions has really changed the experience. That said both HTC sense and Samsung's touchwiz are both absolutely terrible and it makes me cringe that they are most peoples introduction to the OS.

        I only say this to bring it to your attention if you haven't played with latest stock android on the s4 or a similar gen device. If you have and you still hate it more power to you.I know from reading your previous rants/posts/lazywebs you don't want something you have to dick with, you want something that just WORKS and is pleasing to use. I know I'm not objective no one is, but I really do believe they have met that standard.

        • Owen W. says:

          The fact that you have to tell someone to buy from only a special subset of android phones is a sign that something is wrong. But you're correct, Android is great and superior in some ways to iOS. I think a lot of Apple users imagine it's MacOS vs Windows all over again, but the analogy doesn't hold.

        • nooj says:

          Like the Bible, I'm sure he has no idea new android smartphones exist, and has no other avenue to find out about them than by solicitation from random dudes.

    • Josh says:

      You certainly can't just mount a stock Galaxy S III on a Mac as a USB storage device; you have to either use Samsung's Kies app to transfer media or install another app (or root your phone, etc. etc.) to enable it.

  11. pvg says:

    You're screwed, as you suspect - I just tried something reasonably similar. I updated the phone tethered on my laptop after upgrading to iTunes 11.1. iTunes 11.0.whatnot on my desktop will not talk to an iOS7 upgraded phone to sync at all, tethered or wireless. Seems a given 10.7 and iOS7 won't either.
    The various third party apps for moving files to and from the phone still seem to work though, so if it's mostly about moving media files, you can probably still upgrade the phone itself and end up with a new workflow that's just a lot more annoying instead of outright impossible.

  12. Ben says:

    Holy fuck do I regret the day when I accidentally clicked the button in Software Update that forevermore messed up iTunes. The UI of iTunes is so bad that I'm considering buying an android device as my next phone.

  13. Now that iOS 7.0.2 is on its way out, I'm finally considering upgrading to iOS 7, and have stayed on iTunes 10.7 for many of the same reasons jwz has cited ...

    I'm starting to think that the only real solution (for me, anyhow) is to create a thin WinXP VM, install iTunes 11.1 on it, and use that to upgrade, and use iTunes 10.7 in OSX for everything else. :-/

    I suspect the iTunes product manager sucked the iOS 7 product manager's dick a whole hell of a lot in exchange for making iTunes 11 a hard requirement to upgrade to iOS 7, because there's no way in hell I would upgrade to that garbage otherwise.

    • jwz says:

      If you just want to upgrade once, you can do that directly from the phone. The problem comes when you want to regularly sync your phone to your computer, e.g., your music or doing local backups, instead of routing everything through iCloud. You can only do that through the new iTunes.

      Sadly, there was no fellatio involved here, because the real reason is just so much stupider. The only way that MacOS has for communicating with iOS devices is via iTunes. The OS behaves as if the USB drivers are fully contained within iTunes. This means that Xcode also has a hard requirement on a particular version of iTunes, because the way Xcode communicates with your phone is by asking iTunes to do it. And since you can't run Xcode against an iOS that came out later than that version of Xcode, the cascading dependencies kinda-sorta-almost make sense, given that Apple has historically given zero shits about back-porting things to continue to work with the previous release.

      • I could have done an OTA upgrade, if I were a normal Apple user. But, alas, I'm not.

        I stayed on iOS 6.1, in case I wanted to jailbreak the device (I haven't, yet). The sad reality is the OTA upgrade won't go straight from 6.1 to 7.0 or 7.0.2. The device wants to upgrade to 6.1.4, and since Apple has finally disabled the signature server's support of iOS 6, when I try to upgrade to the iOS 6.1.4 that's already downloaded to my phone against my desires, it gets the "Unable to Verify Update" at the verification step. Funny enough, the error message it gives is:

        "iOS 6.1.4 failed verification because you are no longer connected to the Internet."

        I should call AOL and get them to send me a new Internet. Are they still giving out 1,000 free hours of Internet? Because, despite my LTE connection and my Wi-Fi, Apple's localized string for "you're fucked" wants me to believe I'm "no longer connected to the Internet."

        So, yeah, at this point I have to grab the iOS 7.0.2 IPSW and load it using iTunes 11.1. That is, after I bend over and grab my ankles ...

        • Update: By some strange stroke of coincidence, just this morning I woke up to my iPhone 5 telling me that iOS 7.0.2 was available and that I could OTA upgrade to it. This is the first iOS 7 update that it has presented me with: previously it was only offering me iOS 6.1.4.

          Still, I only back up my iOS devices to my local iTunes and don't trust cloud backup (I like having my data; there are useful tools that allow me to extract data from previous backup files, which has been actually useful). So, I guess it's time to install iTunes in a WinXP VM and see how that goes ... :-/