I have just experienced this problem when trying to sync files to my iPhone. I was really puzzled, as I regularly sync files to my iPhone and have never had this problem before. I tried to sync these files over and over again and kept getting the same message. I verified that these files played fine in MM.

When I checked out my iPhone for any clues, I discovered that I had used up all of my storage space. So the reason why MM could not sync the files is that there was no space on my iPhone to do so. After clearing up space on my iPhone, the problem disappeared.

As long as iTunes doesn't open when you connect your device and isn't managing syncing of audio/video you're good to go with sync in MediaMonkey.

Thanks. I have uninstalled what I assume was the Windows store verison and installed the Apple version.

I am reading the instructions for setting it up and these steps do not correspond to anything I am seeing in either iTunes or MM:

Select your device in iTunes and then select the Summary tab of your device
Disable 'Open iTunes when this device is connected'
Enable 'Manually manage music and videos'


There is no Summary tab for my device within the device listing in iTunes and the two commands explained in these instructions are not options in the Summary tab of the device within MM.

So I am unsure how to proceed.

Are you sure it is the desktop version of iTunes and not the Windows Store version: https://www.mediamonkey.com/wiki/index. ... Pod.2FiPad

Hey. Yes, this time MM is asking me to install itunes to sync to the phone. iTunes is already installed on this computer.

Still happens after updating MediaMonkey? Are you sure the files you're trying to sync are playable (that they're on a thumbdrive shouldn't matter, but could mean the files are in the Library disconnected from the drive)? Does the error message state anything more specific about the problem that occurred?

Have you tried copying some files to the local hdd and sync those files?

Anyone else got any advice? I only have 2 days staying with my folks and this is for my mom's iphone.

I'll update MM thanks. Yes, they play fine in MM. I forgot to mention that the files are on a thumbdrive that is plugged into my computer, but since the drive is seen by Windows as just another drive, I don't think that should matter?

Current version is MediaMonkey 4.1.23

Do the files that fail to sync play in MediaMonkey?

Running Media Monkey 4.1.14.1813

Getting "there was a problem synchronizing the following items:" on all files in various playlists I created in Media Monkey thst I am trying to sync to an iPhone 5 running the latest Mac OS. I have installed iTunes to the laptop and MM is recognizing the iphone.

Could anyone assist?