Why doesn't my entire playlist Sync?

I have many playlists that this is happening with. I have a iPhone 6Plus. For example, one playlist on my iMac has 98 songs in it. I have that playlist set to sync with my iPhone. After the sync is done out of the 98 songs only 26 show up on the iPhone. Another example, a playlist that has 669 songs on iMac only syncs 395 of them. There doesn't appear to be a common thread. The songs that do sync are a combination of Purchased and ripped from CD, Not one or the other. If I turn on show all music on the iPhone they are all there with the balance having a cloud for download next to them. I even tried doing a iPhone reset and started from scratch. No help there either. (side note. If you reset to factory you have to redo all your Apple Pay cards... a P.I.T.A.!) Anyone have ideas? Oh, and also, this is a 128gb iPhone, so it's not a space issue. There is 30+ GB of free space on phone. Phone and iMac are both updated with the newest software.

New information. Looking a little closer, it looks like all the songs that are not syncing are all Purchased tracks. But some Purchased tracks DO sync.

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Why doesn't my itunes library sync songs I've purchased with an old Apple id?

Hello all,
I've recently bought a replacement laptop, running Windows 7 & had my music library transferred from my old P.C successfully.
When I sync my ipod over 700 songs don't sync, but they're all available to play from the library.
At a glance it would appear the majority of these songs I've purchased from the itunes store at some point.
I'm advised that I will need to log in to the old itunes id to authorise this computer, but this is not possible as the email address has been deleted.
I contacted the bank from which the account was used to purchase these songs & the only debit card details they had on file were not the correct card.
So, where do I go from here? This is my music that I purchased legitimately from the itunes store & I want it all on my ipod which again, was legitimately purchased from Apple.
Any advice will be greatly appreciated!
HWM2

You should have just switched the email address on your apple id to your new one, instead of creating an entirely new apple id.
But, go to appleid.apple.com and try to reset your password using the security questions method, instead.
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I have the same issue with my iPhone 5 (iOS 7.0.4) on a Windows7 PC updated with the very latest iTunes. My other iPode (nano - old and new) sync just fine. Only my phone is affected.
I have one album I purchased from iTunes that won't sync via a plain playlist that I made just for that album. (The song files transferred to my phone as part of the "purchased" category. But I can't sync a playlist made on my computer containing those same songs.)
Another plain playlist I made for some spoken short story files in my library won't sync either.
There are no error message that appear while syncing; nothing stating that songs didn't transfer.
Also, if I try to make a new playlist on my phone and adding the "purchased" files to it, the album cover is wrong. The files will be available in the playlist that way, but with the incorrect artwork. (No idea what happens yet if I re-sync with this phone-make playlist.)

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Thank you Julian, I think your idea might end up in a solution.
Even though my phone (Nokia 6230) doesn't have the "Send all contacts" option, I tried to send an individual vCard for testing purposes: the address book accepted it with arms wide open (like that silly Creed song). Because I'm stubborn, I tried to sync my phone with my one-contact address book and ended up with two different people on my phone with exactly the same name and number (along with everybody else fortunately...).
I'm guessing if I do this for the WHOLE cell phone contact list, I'll have an address book on my mac by Christmas eve . I'll mark this question as answered when I'm done doing this and follow the rest of your advice.
This raises two important questions:
- What happened in the first place?
- Is Apple going to develop a more complete syncing software where weird things such as these do not happen?
Any thoughts on these issues? It really annoys me when I don't understand what's wrong with the equipment I use...
Thank you for your time and patience.
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Why doesn't using EAS to sync Drafts from server to client work anymore?

Hi All,
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It has always been possible, however, to download emails from the Drafts folder and to sync the Drafts folder like any other folder. Recently, however, I have been having problems performing this sync. These problems are occuring on Office-365. Other users
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=================
[EAS] Client Sends:
================
<Sync xmlns="AirSync:">
<Collections>
<Collection>
<SyncKey>0</SyncKey>
<CollectionId>4</CollectionId>
</Collection>
</Collections>
</Sync>
======================
[EAS] Received from Server
======================
<Sync>
<Collections>
<Collection>
<SyncKey>1335200247</SyncKey>
<CollectionId>4</CollectionId>
<Status>1</Status>
</Collection>
</Collections>
</Sync>
=================
[EAS] Client Sends:
=================
<GetItemEstimate xmlns="GetItemEstimate:">
<Collections>
<Collection>
<airsync:SyncKey>1335200247</airsync:SyncKey>
<CollectionId>4</CollectionId>
</Collection>
</Collections>
</GetItemEstimate>
======================
[EAS] Received from Server
======================
<GetItemEstimate>
<Response>
<Status>4</Status>
<Collection>
<CollectionId>4</CollectionId>
</Collection>
</Response>
</GetItemEstimate>
================
[EAS] Client Sends
================
<Sync xmlns="AirSync:">
<Collections>
<Collection>
<SyncKey>1335200247</SyncKey>
<CollectionId>4</CollectionId>
<DeletesAsMoves/>
<GetChanges/>
<WindowSize>64</WindowSize>
<Options>
<airsync:MIMESupport>2</airsync:MIMESupport>
</Options>
</Collection>
</Collections>
</Sync>
=====================================
This receives an empty reply indicating no changes
Here are the HTTP Headers:
=====================================
Headers: {
"Cache-Control" = private;
"Content-Encoding" = gzip;
"Content-Length" = 119;
"Content-Type" = "application/vnd.ms-sync.wbxml";
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Vary = "Accept-Encoding";
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Thanks!
-Rich

Hi Tom,
Thanks for following up on this and providing a definitive answer. It is much appreciated.
The decision they have made to block the Drafts folder syncing is mildly disappointing.
Unfortunately, the mechanism by which they are implementing this makes it a more serious issue.
Specifically, they should not be returning a Status of 4 in response to the GetItemEstimate for the Drafts folder. That Status of 4 effectively says, "Try Again". See section 2.2.3.162.6 of the MS-ASCMD document.
Instead, they should probably return a Status of 1 and an Estimate of 0. This would be the appropriate match with their empty collection in response to the Sync command.
Alternatively, they could return a Status of 2 indicating, "an incorrect folder was requested".
Or they could simply omit the folder from the FolderHierarchy response.
By returning a 4 and requesting that the client try again, they can cause the client to enter a continuous (and infinite) stream of GetItemEstimate requests. By following the documentation from 2.2.3.162.6, a client would get into this loop:
1) GetItemEstimate returns 'Invalid sync key'
2) FolderSync returns status OK
3) GetItemEstimate returns 'Invalid sync key'
4) FolderSync with syncKey 0 returns Status OK
5) goto 1
Thanks,
-Rich

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Notes
Before anyone mentions the lame suggestion of "Restoring", let me add that I have done that. Alot.
I'm pretty good with computers, so please get as nerdy as you want, just as long as you're only trying to help me.
This disscussion should only be about this particular problem, please refrain from posting you're problems to this (Make your own discussion).
If necessary, contact me via email if you need more information, or have other misc. questions or inqueries.
Basic Information
Product: iPod classic
Serial Number: ******0YMV
Model: MB147LL
Version: 1.1.2 PC
Capacity: 80GB
Diagnostics
Retracts: 14
RealLocs: 4928
Pending Sectors: 120
PowerOn Hours: 443
Start/Stops: 16585
Temp: Current - 31c
Temp: Min - 3c
Temp: Max - 67c
Additional Details
The iPod works fine after immediate restoration, however, after adding 500 or so songs it seems to quit responding and appears to terminate communications with computer while freezing iTunes. After fiddling around I usually grow tired and unplug it and iTunes quickly displays a message saying to restore the iPod, although it's unplugged... This happens everytime, so it's not a rare situation for me. I've tried repeatedly on two Windows computers and a brand new Mac.

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Why doesn't my entire playlist Sync?

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