I am running a Windows 11 installation on Parallels 17 on my Mac with OS 12.4.

On this Windows I run iTunes and an installation of Outlook. I sync my phone via the USB cable. This is the only way I know how to use an Outlook calendar and sync it with an iPhone.

I tried to restore my iPhone from the backup in this iTunes instance using the USB cable. Everything seems to work OK at first: iTunes calculates the time it takes and the phone shows "Restore in Progress". Then the phone reboots - and iTunes shows an error message saying that the restore failed. The phone starts up to the same state prior to restore.

I am assuming this is because with the phone reboot the virtual machine loses its connection to the device. Is there any way I can still restore my phone from the backup-ed version?

Can I transfer the backup under Windows to an iTunes instance on Mac and use it to restore the phone under Mac OS?

  • 1
    Outlook calendars, any many other things, can be synced via CompanionLink. Normally VM's offer the ability to reconnect USB devices on the fly, but I've never used Parallels - have you tried accessing the VM using RDP, as usually the RDP connection GUI will allow reconnecting USB devices. General FYI: iTunes has limited functionality for backups - have you considered iMazing? It's one of the best iPhone backup and data management programs I've come across, and it's worth the license fee for the functionality it offers
    – JW0914
    Feb 9 at 14:28
  • 1
    Parallels has an option to connect to a specific location, Mac or VM. Devices menu > USB & Bluetooth.
    – Tetsujin
    Feb 9 at 17:30
  • I am aware that I can pass USB deviced through to the VM. The problem I am describing is not a generic USB connectivity issue. As described the restore workd fine intially. My problem occurs when the iPhone resets and thereby loses the connection to the VM. ------ My work-around now was to copy the desired iPhone backup under Windows, shift it over to the backup location of iTunes under Mac and restore the phone under Mac OS. And yes - iphone backups are the same for Win and MacOS.
    – Pat
    Feb 12 at 12:31
  • Why that happens has been thoroughly explained in comments below your other question: superuser.com/questions/1829220/… . This is just a lack of understanding how virtualization works. Feb 12 at 12:33


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