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theorist9

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May 28, 2015
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I'm using a 7th Gen iPod Nano to listen to Audible audiobooks and music. Since I'm regularly getting new audiobooks, I frequently need to change what's on my Nano--deleting old books and adding new ones. There's also a lot of music on there, but I rarely change that.


Here's the process:
1) Download new audiobooks from audible.com onto my 2014 15" MBP running MacOS 10.13.6 (High Sierra).
2) When they're finished downloading, I double-click on them, which loads them into iTunes (12.8.3.1).
3) I go into iTunes, click on the Nano icon, and go into audiobooks, uncheck the ones I want to remove, check the ones I want to add, and then hit Apply to resync the Nano with what I'd designated, in iTunes, as the Nano's updated content.

This used to work without issue. However, starting a few month ago, I occasionally ran into a problem where it thought the iTunes library on the Mac was different from the one on the Nano, and thus gives me the message shown below.

And since then it's gotten worse--I now need to go through this process nearly every time I want to add a new book. What's puzzing is that none of the relevant software has changed. The only possibly relevant change I can think of is that I recently updated the contact email for my iCloud account.

This is a real inconvenience, because the only way to add new content is to hit Sync and Replace. That allows me to add new audiobooks, but only after deleting the existing content of my Nano. I then have to re-copy all the music, which takes several minutes.

1710384519940.png
 
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Slix

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Mar 24, 2010
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I'm using a 7th Gen iPod Nano to listen to Audible audiobooks and music. Since I'm regularly getting new audiobooks, I frequently need to change what's on my Nano--deleting old books and adding new ones. There's also a lot of music on there, but I rarely change that.


Here's the process:
1) Download new audiobooks from audible.com onto my 2014 15" MBP running MacOS 10.13.6 (High Sierra).
2) When they're finished downloading, I double-click on them, which loads them into iTunes (12.8.3.1).
3) I go into iTunes, click on the Nano icon, and go into audiobooks, uncheck the ones I want to remove, check the ones I want to add, and then hit Apply to resync the Nano with what I'd designated, in iTunes, as the Nano's updated content.

This used to work without issue. However, starting a few month ago, I occasionally ran into a problem where it thought the iTunes library on the Mac was different from the one on the Nano, and thus gives me the message shown below.

And since then it's gotten worse--I now need to go through this process nearly every time I want to add a new book. What's puzzing is that none of the relevant software has changed. The only possibly relevant change I can think of is that I recently updated the contact email for my iCloud account.

This is a real inconvenience, because the only way to add new content is to hit Sync and Replace. That allows me to add new audiobooks, but only after deleting the existing content of my Nano. I then have to re-copy all the music, which takes several minutes.

View attachment 2358886
Have you tried:
- Restarting the Mac, and iPod?
- Restoring the iPod and syncing it from scratch again?

I've not seen this happen before, so I'm just throwing ideas out there, but hopefully you find a solution.
 

theorist9

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Original poster
May 28, 2015
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Have you tried:
- Restarting the Mac, and iPod?
- Restoring the iPod and syncing it from scratch again?

I've not seen this happen before, so I'm just throwing ideas out there, but hopefully you find a solution.
Have restarted both several times since this began. But I can't recall how recently I restored the iPod. I'll give that a shot.
 

Slix

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Mar 24, 2010
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How does one do that?
There is an option in the main sync screen for the iPod that says "Manually manage music, movies, and TV shows".

I never manually manage any of my iPods because it feels like a waste of time to select everything each time and I think play counts don't sync if you do that, so I don't know if that is the issue here.
 
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Slix

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Mar 24, 2010
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I've only ever manually managed my music on both my iPhone and Nano Gen 7. I'm a control freak and don't trust SYNCH as it changes items I want to keep and adds items I don't want.
I've never had this issue. Playlists don't change unless you want them to, with the exception of Smart Playlists, which I want to do that automatically. What are you trying to sync that causes this?
 

theorist9

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May 28, 2015
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I've never had this issue. Playlists don't change unless you want them to, with the exception of Smart Playlists, which I want to do that automatically. What are you trying to sync that causes this?

Sorry, I'm confused—doesn't this already address your question? Or are you asking something different?
Since I'm regularly getting new audiobooks, I frequently need to change what's on my Nano--deleting old books and adding new ones. There's also a lot of music on there, but I rarely change that.


Here's the process:
1) Download new audiobooks from audible.com onto my 2014 15" MBP running MacOS 10.13.6 (High Sierra).
2) When they're finished downloading, I double-click on them, which loads them into iTunes (12.8.3.1).
3) I go into iTunes, click on the Nano icon, and go into audiobooks, uncheck the ones I want to remove, check the ones I want to add, and then hit Apply to resync the Nano with what I'd designated, in iTunes, as the Nano's updated content.
 

Slix

macrumors 68000
Mar 24, 2010
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2,413
Sorry, I'm confused—doesn't this already address your question? Or are you asking something different?
I was asking what @Soondae is trying to sync that causes it to delete/add random things they don't want.

@theorist9 Did you end up figuring out why your iPod kept trying to Sync and Replace instead of a regular sync?
 

theorist9

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May 28, 2015
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I was asking what @Soondae is trying to sync that causes it to delete/add random things they don't want.
Ah, got it.

@theorist9 Did you end up figuring out why your iPod kept trying to Sync and Replace instead of a regular sync?
No, didn't figure out why.

The most obvious explanation is gamma rays from poorly shielded experiments at the university across the street causing bit flips. That would also explain why my skin is turning green.

But I did try your Restore suggestion, and didn't have the issue on the last Sync, so that may be the winner! I just need to do a few more Syncs to be sure the fix wil stick. I'll report back in a month or so, by which time I'll probably have done a few more Syncs.
 
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theorist9

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May 28, 2015
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@Slix , @philden , @Soondae

I found what was causing the sync issue!

If I eject the iPod from within iTunes, there is no issue the next time I connect my iPod.

But if I eject the iPod from within Finder, then the next time I connect I get the sync issue!

 
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