Take a look at the following thread, it sounds an awful lot like what you're experiencing.
From what I can gather, many people have sucess by in iTunes selecting the "music" underneath the iPhone entry (where you should see the greyed out songs) and then deleting the greyed out songs and trying to sync again.
Other sugguest right clicking the greyed out song and Create an AAC version and then syncing.
Some different options to try, take a look at the thread though, you aren't the only one having his issue.
No errors pop up, no.
I already read that entire discussion before I posted. I also read all 11 pages of this discussion:
The solution you mention is for people that have corrupt songs, which I have isolated is not my issue.
I've deleted the greyed out songs countless times, and resynced. It still cancels sync on the same "number" song as when it previously did, assuming I have changed no other options.
I have also converted, deleted, and unchecked songs where the sync would be canceled. Most often it will just "cancel sync" at the same "number," which is of course a different song, since the last song was removed, converted, or unchecked.
Corrupt songs are not my issue, because if I drag and drop the individual songs that have "canceled snyc," they transfer without an issue. Sometimes I can get 13 songs to transfer, before sync get cancelled and sometimes I can get a couple thousand, before it cancels. It does not seem to be an issue with particular songs. Not to mention, my iPod Classic has never "canceled sync" prematurely on me, and has no issue with syncing all 6000 of my songs.
I have had moderate success at manually syncing blocks of 500 songs at a time, but that has been far from fullproof, and quite a pain. This has allowed me to get about 2500 songs on my phone, but it's a gruelling process.
I have the same issue.
I have tracked the issue down to songs that were purchased on iTunes, on the phone.
All of those songs are in my Macbook Pro iTunes library. Once complete sync takes place, my iphone 5 still says some of those songs are not on the phone.
Thi has only happened since upgrading from 4S to 5.is
I wish I was able to isolate this to particular songs and just delete them, but that hasn't worked. I deleted or converted about 50 songs, and it would still hang up on, for instance, the 11th song to sync, which would be a different song that it hung up on before, but at the same numeric point in the syncing process.
Whenever I am able to isolate a song, I can just individually drag that song to my devices, and it doesn't "cancel sync." I can every drag and drop that isolated song with other songs, but if I do "too many" it will "cancel sync" prematurely.
Why can my iphones sync as perfectly as my ipod Classic, which syncs perfectly all the time? I guess I wasted money on my 64GB iPhone 5. I should have just gotten the 16GB and not put any songs on it.
I am having the same problem with my iPhone 4. It was fine until about a month or two ago. I usually just plug my phone in the wall to charge and never sync with my computer. But I did a couple months ago. Ever since then I have the greyed out songs and cannot play them on my phone. For a while they were grey on my computer too. I don't know what I have done but I have since gotten them all ok on my computer. Then tonight I changed to Shared music instead of My iPhone, And it played all the songs fine! Until I disconnected the phone from the computer and logged out of iTunes. Now NONE of my songs will play on my phone. They are no longer grey but nothing will play now at all. I am getting very frustrated!!!! I tried to call Apple to ask if there was a solution to this problem. I could not even get to talk to a live person unless I paid them $35 because my phone is soooo old at a wopping 2 years! I am not impressed at all!!!
I was pulling my hair out because it would start all fine then out of no where stop on me. Turns out I had to figure it out on my own... My problem was that my girlfriend gave me an album for my birthday with a digital download card with it. When I downloaded the album and put it on itunes it worked but it was the reason, I couldnt put it on my phone. Once the album was deleted then all my songs went on. Figures lol pay for music and run into trouble.
I just had the identical problem as you. I rang Apple support and found out that you need to reset the sync history. The link for doing so is here:
The link is Mac only not too sure where the one for windows or other OS are but if you look you'll find it. It is pretty straight forward all you have to do is select your OS and then copy and paste the code into utilities and press enter or return. It worked for me.
Even I faced the same problem
After 3-4 weeks of discussion with apple customer care and apple's engineering. I finally got the Solution for this issue by following this link.
The information in that link is worthless. I did everything in it. The problem persisted. I also tried resetting the phone to virgin condition and then restoring from iCloud. That did not fix the problem. I had to reset the phone to virgin condition and then set up as a new phone. Wasted a lot of time.