It’s a pain in the butt to get any of it working. Go figure. You knew (should have known) that you were getting yourself into this kind of thing when you installed 64-bit XP in the first place.

THE BOTTOM LINE: You can install iTunes 8.2 and have it sync with an iPhone (or iPod) in your 64-bit version of XP. If you have a previous version of iTunes installed you may want to uninstall everything involved with iTunes before installing a new version, but there are reports that you may not need to. You will not be able to use that PC to install updates to the iPhone OS; you will have to use another computer that iTunes fully supports.

Most of my information comes from this wonderful page. One problem with it: the new iTunes came out today (version 7.7) including the new iPhone app store and the download link on that site is for an older one. Further problems: with this setup method the Apple Update doesn’t update your iTunes automatically. Here’s the link I’m downloading right now: iTunes 7.7.0.43 (July 10, 2008)

The only way I managed to get the link was by using the User Agent Switcher extension for Firefox to spoof Apple’s website into thinking I was running Vista x64. You can get the latest copy of 64-bit iTunes by installing the extension, then adding a new user agent in the options. In the description field put “Firefox 3.0 (Vista 64)“, for the platform field put “Win64“, and finally for the User Agent field:

Mozilla/5.0 (Windows; U; Windows NT 6.0; Win64; x64; en-US; rv:1.9) Gecko/2008052906 Firefox/3.0

Save that, go to Tools > User Agent Switcher and pick your new one. Then go to the iTunes download page and it should serve up the 64 bit version for you. (I think the iTunes download ignores whether your browser reports a 64 bit operating system and just gives you the option of a 64 bit download if it detects Vista.)

Once downloaded, use WinRAR or 7-zip to open that setup file and extract the Quicktime installer if you don’t have a recent version. Either way, you will also need to extract the Mobile Device Support installer and the iTunes installer to a separate folder.

I already had the previous 64 bit version of iTunes installed and I uninstalled it before proceeding. I don’t know if this is necessary, however. I do know that it is necessary to reinstall the Apple Mobile Device Support, and it’s probably a good idea to uninstall any older version of that as well.

Download and install Microsoft Orca from here or use either of those two previously mentioned archive managers to extract the same file from this CAB file. Go ahead and install the Mobile Device Support (assuming Quicktime is already in place), and while that’s working open the iTunes installer with Orca. Look down the column on the left for “Launch Condition” and then select it. On the right change “VersionNT64>=600″ to “VersionNT64>=501″, click save, then exit. As soon as the Mobile Device Support is done installing, fire away at the iTunes installer. Don’t be worried if it tries to install to “Program Files (x86)”, just let it go on its way or pick your favorite folder instead. If you find yourself running in to an error 2229, then I’ve found these instructions should help you. I never had that error message, so I don’t know if it will work or not:

2229 has been worked around at PlanetAMD64 by user “arth” over at the forum:

“I got an error when trying to install, error code 2229. To solve the problem I dropped the LauchnConditions table and in InstallExecuteSequence and InstallUISequence tables deleted the LaunchConditions action. After that save the MSI file and close ORCA”

When you first plug your iPhone in, XP will detect it as a digital camera, but you have to tell it otherwise. Right click on My Computer to bring up the properties. Go to the hardware tab, and bring up the device manager. Open the section for imaging devices, right click on the iPhone entry and choose to reinstall the driver. Click through the wizard choosing to go the advanced route and manually choose the driver to install. Tell it ‘Don’t Search…’, and eventually you will be able to pick a new driver: “Apple Mobile Device USB Driver” instead of the generic imaging device driver. iTunes will recognize the phone after windows finishes setting up the new driver.

With this setup so far, I’ve heard reports that CD burning might not work (I wouldn’t know, I don’t burn CDs with iTunes). To fix it, download and install these 64-bit burning drivers; then (I’m assuming your root drive is C:\) create this folder structure: C:\Windows\Sysnative\drivers Copy the file C:\Windows\system32\GEARAspiWDM.sys over to that new drivers folder you created, and from what I hear, that should clear up any problems you might have in burning CDs.

From there almost everything is good to go except for one gapeing problem and one minor problem. The driver for my iPhone doesn’t work when it goes into recovery mode as part of the firmware upgrade process, so I had to do the upgrade to 2.0 firmware on a 32-bit Windows. Once I did make it through the upgrade process it worked just fine back in 64-bit land. Any insight into that recovery (iBoot) driver would be much appreciated. The minor problem: I completely didn’t notice that when Windows accesses the iPhone as an imaging device it can’t get any of your pictures from it; it’s always empty. (Thanks, paxos)