Hello. Recently I've faced the problem after the upgrade of iPhone from iOS9 to iOS10, that one of my older macbooks pro was thrown out of sync by Apple. It's because you have to use iTunes 12.5+ to connect your upgraded iPhone, or it will give you the "false response from iPhone" message and nothing will work. But on some Macs you can't upgrade iTunes higher that 12.2, so as on one of my mbps with Mac OS Lion 10.7.5. So here is my tested and workable Solution#1 to overcome this problem (iTunes+iPhoto). Tested on MacBook Pro 2.1 (2006) with 3gb RAM (actually 4, but it uses only 3 due to EFI32), primary SSD, and secondary HDD (installed via optibay instead of CD-Drive). I beleive that this solution will work on some less performant configurations. 1. Download and install Virtual Box appropriate build (4.3.40 for me): https://www.virtualbox.org/wiki/Download_Old_Builds_4_3 2. Download and install Virtual Box Extension Pack from the same page. 3. Find or create yourself OS X Mavericks ISO (Solution is tested with Mavericks, but I think newer OS version could be ok too). 4. Create Virtual Machine with minimal settings (sound could be turned off) using this OS X Mavericks ISO. (Attention: choose USB2.0 in virtual machines settings, or you won't be able to connect iPhone to it). 5. Install, configure and update OS X Mavericks with all the latest updates, including iTunes 12.5+. 6. Install iPhoto 9 and upgrade it to 9.4.3 on host (your Mac) and guest (your Virtual Machine). https://support.apple.com/kb/dl1650?locale=en_US 7. Choose where to store the iPhoto media library on host (your Mac) and set up this folder sharing. 8. Connect this folder on guest (Virtual Machine) and add it to startu-up items so it will be available every time you start your VM. To do so folllow these steps: - Choose Apple menu - System Preferences, then click Users & Groups. - Select the user, then click Login Items. - Add shared folder or drag'n'drop it to the list. - Check the "hide" box. 9. Now set up where to store the iPhoto media library on guest (Virtual Machine) and choose the previously created media library on host (your Mac) via shared folder. From now on, you can plug in your iOS10 iPhone to USB, choose "devices" menu in Virtial Box for your Virtual Machine, select your iPhone and it will connect to your VM. You can now open iPhoto on your VM, import the photos, and then use them as the same media library on your host (Mac). A bit more hard to sync iTunes due to its different versions, but it's possible. 10. From iTunes on your host (Mac) choose where to store the media library (or leave as it is). 11. Share this folder as before. 12. On guest (VM) in iTunes choose this folder to store its media library too. 13. Share the Music folder on your host (Mac) where iTunes stores its metadata (it's not movable as long as I know). 14. Create application in Automator on guest (VM): - Go to Music folder on guest (VM) and move all the folders and files inside it to trash - Connect to shared Music folder on host (Mac) and copy the iTunes folder from there to the Music folder on guest (VM). - Empty the trash (possible via applescript, google for this code) Optional: you can also enhance automator script by mounting and unmounting drives and saving passwords for shared folder access login and password into your keys. Be sure that the user account and password you try to login with from guest on host are added to the access to this folder on host with read/write option. (If your application copies not only the iTunes folder but all from Music folder, try to check "Ignore previous" when getting specified item step is taken before copy in Automator). 15. From now on, you can use iTunes on your host (Mac), like downloading music. And when you want to sync it with iPhone, just run the Automator App script on guest and all your media will be available in iTunes on guest. From there you can connect to your iPhone (devices-choose iPhone from the list in the VM menu) and sync it. There is a little problem with backups in this solution. As well as I know you can't move the location of your device backups in iTunes, so you will have to make the size of your VM virtual hard drive appropriate to handle the system (20gb) plus the size of your iPhone. In that case always remember to backup your device backup file from the iTunes on guest (VM) before deleting it. The backup files stores at ~/Library/Application Support/MobileSync/Backup/. P.S. I will attach the reference of an Automator file and try to update the post if there will be some enhancments made for this solution. P.P.S. This will work of course until Apple will change the metadata structure of newer iTunes so much, that it won't be possible to just import the metadata folder form iTunes 12.2 and make it work. In that case we could try to find another way to sync metadata, without duplicating actual files for two libraries. Thanks and good luck.