How To Sync Your iPhone 3G Using Linux and Vmware

How To Sync Your iPhone 3G Using Linux and Vmware

Since I purchased my new iPhone 3G a few weeks ago, I’ve been happily syncing it with my MacBook Pro. As much as I love my Mac laptop, most of my day to day work is done primarily on my personal desktop running Ubuntu Linux. I thought now would be the ideal time to move all of my music-related activities entirely from OS X to Linux. So, I recently migrated all of my music there (35+GB!), and have been trying out a handful of open source solutions for managing my music collection (SongBird, Rhythmbox, Amarok, etc.). What I’ve quickly learned is that most of these applications work fairly well, however they don’t integrate with the Apple Store (love it or hate it, they’ve got great content) and you can’t sync yet with the iPhone 3G.
Since I’m already running VMware Workstation (XP SP2), I thought it would be a breeze to download the latest version of iTunes and sync away. That dream unfortunately did not come true! It took a little while but after I imported my music library from a shared folder, I decided to plugin the iPhone. I waited….. waited….. and nothing happened! I restarted iTunes and got a most obscure error message:

“iTunes could not connect to iPhone “” because an unknown error occurred. (0xE8000035)”

After an inordinate amount of Googling, It seems this has been a common problem affecting both VMware and VirtualBox users. There was a mixture of comments. Some users said things where working fine for them, others gave up with tears in their eyes. From what I could gather, here were the most common suggestions for solving the problem:

  1. Upgrade from Service Pack 2 to Service Pack 3
  2. Enable USB 2.0 in your VM preferences
  3. Try plugging the phone into a different USB Port
  4. Set ehci.present to TRUE in the .vmx file
  5. Try running the VM in VMWare Player instead of VMWare Workstation

I can safely say that *none* of these suggestions helped. The first, and most time consuming, thing I tried was upgrading to SP3. No luck! USB2.0 and EHCI where already enabled so that couldn’t be it either. Different USB ports didn’t help, and VMWare Player behaved exactly the same. As an absolute last resort, I decided to download the latest version of Workstation. My version 6.0.2 was from about 7 months ago, and I noticed that 6.0.5 was released at the end of Aug. The solution that worked for me?

Upgrade to the latest version of VMware!!

Why did this work? I browsed through the release notes, and saw mention of an iPhone-specific fix in version 6.0.3:

“With Workstation 6.0.2 the iPhone might be seen as a camera device by a Windows guest but iTunes did not list the device in its device list. In Workstation 6.0.3, the iPhone is usable and visible in iTunes for Windows guests.”

Problem solved and my iPhone is now happily syncing away with my virtual instance of Windows XP. I figured I would share this post and spread the word in case there are other hopeful, but stumped, iPhone 3G users out there.

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7 Responses

  1. andreas says:

    thanks 🙂 i’m waiting for my iphone.. but as a linux user, i think it’s better to be prepared *gg*
    best wishes from vienna,

  2. stef_fr_37 says:

    I’m using a Ubuntu hardy heron distrib, with a version 6.5.1 version of vmware workstation. Do you try this version to sync your iphone ? And do you try to make an update of your iphone firmware on your xp guest.
    Thank you for your answer, il want to buy an iphone, but i’m scared to not be ble to sync it or update it.
    Thank you

  3. ericblue76 says:

    Hi Stephanie,
    Believe it or not, I’m still a bit behind the times with my Ubuntu server. I’m still on 7.10 (Gutsy) and am only on running VmWare Workstation 6.0.5.
    In theory, you should be fine with Hardy and 6.5.1. Syncing works fantastic, however I did have an odd experience while upgrading the firmware. For whatever reason, during the upgrade the USB interface kept switching back and forth between host and guest. I actually needed to complete the upgrade on my Mac. I’m sure this problem is easily solved, however I haven’t spent the time to research.
    Good luck!

  4. stef_fr_37 says:

    Thank you for your answer,
    I believe you because it is sometimes annoying to update your distrib and reinstall vmware, and/or others apps not available on deposits… For this, I did not update to Ibex 😉 On the other hand the last vmware workstation is very cool, with its “unity” mode.
    I have another question, do you know if i can (i bought my iphone today !!!)
    sync my iphone with my guest xp on vmware and update the phone on another windows pc (a real one, not a virtual). To sum up is it possible to sync an iphone on two or more pc ?
    Thank you

  5. ericblue76 says:

    Yes, you can sync with the VM and upgrade firmware on another PC. However, (AFAIK) you can not sync Photos/Videos/Music with 2 different computers.

  6. Derek says:

    I’m using SLED10 (SuSE) and vmware workstaaation 6.5.x. I have no trouble syncing even though it’s painfully slow. However, EVERY attempt to update the firmware results in a bricked iphone. I then have to use my wife’s windoze laptop to unbrick it and do the update. Then back to my machine with vmware to resync.
    It seems to be an issue where the USB port is shutdown for a moment during the mode switch on the iphone, resulting in a disconnect with vmware. Of course, that then results in the inability to reestablish the connection between iTunes and the iphone in order to complete the update.
    If someone has come across a fix or workaround for this, please share!!!

  7. zafer says:

    i have xp (sp3) vmware(workstation 6.5.1) image running on my opensuse 11.1 notebook
    i have problem connecting to iphone with itunes.
    i had this error message.
    “itunes could not connect to the iphone ~~ because an error occured while reading from device”
    Could you help some body?

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