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Any ideas?
Since I travel for work and have two workstations at home a several laptops, my goal was to build a dedicated "iTunes" VM and always sync all devices to that, since you can only sync an Apple device with 1 copy of Itunes at a time without over-writing the entire device.
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Microsoft Windows Vista Ultimate Edition Service Pack 2 (Build 6002)
VMware, Inc. VMware Virtual Platform
iTunes 9.2.0.61
QuickTime 7.6.6
FairPlay 1.8.20
Apple Application Support 1.3
iPod Updater Library 9.2d4
CD Driver 2.2.0.1
CD Driver DLL 2.1.1.1
Apple Mobile Device 3.1.0.62
Apple Mobile Device Driver 1.49.0.0
Bonjour 2.0.2.0 (214.3)
iTunes Serial Number 57DF82DXXXXXXXX
Current user is an administrator.
The current local date and time is 2010-07-07 17:14:00.
iTunes is not running in safe mode.
WebKit accelerated compositing is enabled.
HDCP is not supported.
Video Display Information
VMware, Inc., VMware SVGA II
**** External Plug-ins Information ****
No external plug-ins installed.
**** Device Connectivity Tests ****
iPodService 9.2.0.61 is currently running.
iTunesHelper 9.2.0.61 is currently running.
Apple Mobile Device service 3.1.0.0 is currently running.
Universal Serial Bus Controllers:
Standard Enhanced PCI to USB Host Controller. Device is working properly.
Intel(R) 82371AB/EB PCI to USB Universal Host Controller. Device is working properly.
No FireWire (IEEE 1394) Host Controller found.
Connected Device Information:
iPhone 3GS, iPhone 3GS running firmware version 3.1.2
Serial Number: 889XXXXXXXX
Most Recent Devices Not Currently Connected:
iPad running firmware version 3.2
Serial Number: VXXXXXXXXXXX
**** Device Sync Tests ****
Sync tests completed successfully.
One thing you could try (since you've reinstalled the OS) is to download a previous version of iTunes. 9.1, 9.0.
http://oldapps.com/itunes.php






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1) I have multiple Apple devices - ALL of them (even the iPad when it first came out of the box) had this problem - NONE of them will backup or sync in a VMware Workstation Guest.
2) When I launch iTunes on the HOST computer (not in a VMware Workstation Guest) all of the devices - jailbroken and otherwise, can backup and sync perfectly everytime.
Since the only difference between working and not working is VMware versus no VMware, I do not believe it is specific to a particular iPhone.

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If the only reason for doing this is so you can sync music from multiple computers, you can do this by using manual mode. If you just want to sync music from one computer and the calendar from another computer, you can do this also. On the itunes where you just want to sync the calendar, it will ask you something about replacing the music or something, just click cancel and it will sync just the calendar or whatever.






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Apple Hardware
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All of Apple's hardware is produced solely by Apple Inc., who determines internal systems, designs, and prices. Apple buys certain components wholesale from third-party manufacturers. The current Mac product family uses Intel x86-64 processors. All Mac models ship with at least 1 GB RAM as standard. Current Mac computers use ATI Radeon or nVidia GeForce graphics cards and include a dual-function DVD and CD burner, called the SuperDrive. Current Apple hardware includes the iPad, iPhone, iMac, Mac Pro, Macbook, iPod and Apple TV. Discontinued hardware includes the Apple I, Apple II, and the Apple III, the Lisa, the Newton, the Quadra, Performa, Centris, Macintosh II and LC series, the Power Macintosh, iBooks and the MacBook.