Copying 4.3 GB music files, including devotional music files, and smart playlists from iPod Nano 4th Gen to iPod Touch 2nd Gen

This post follows up on my previous post, Revival of my old iPod Touch 2nd Gen device; Useful pocket scripture, including Hindu scripture, ebook reader, https://ravisiyer.blogspot.com/2017/09/revival-of-my-old-ipod-touch-2nd-gen.html, dated 30th Sept. 2017.

I have an iPod Nano 4th generation which has a lot of devotional music - Hindu, Muslim, Christian, and Multi-faith mostly of popular type but a few Indian classical type (Carnatic and Hindustani) as well as pop songs in Hindi, English and some Telugu too. Very importantly, it also has some songs sung by Bhagavan Sri Sathya Sai Baba himself - I heard some of those songs today (and yesterday). In Bhagavan's physical form absence, hearing him sing these songs is a very moving experience for me!

This music set runs into 958 songs taking up around 4.3 GB, with my iPod Nano being an 8 GB device. I had invested a lot of time a few years before Bhagavan Mahasamadhi (April 2011) in tagging the songs and then creating smart playlists in iTunes to create lists of songs on Rama, Krishna, Shiva, Devi, English Christian etc. categories. Prior to Mahasamadhi I thoroughly enjoyed and had devotional bliss kind of experiences listening to these devotional songs. But I must also say here that I also enjoyed (and still enjoy) listening to non-devotional pop songs too (both Hindi and English, as well as some Telugu songs). After Mahasamadhi, I went through some really weird times and was not really listening to the iPod Nano songs much. Now I hope to get back to listening to these songs on the iPod Nano connected to a Logitech iPod speaker on a more regular basis.

As now my iPod Touch 2nd Gen. which is also an 8 GB device, has been revived, I thought of copying my iPod Nano 4th Gen. music set onto my iPod Touch. Earlier (before Mahasamadhi) I was using my iPod Touch primarily as an ebook scripture reader and so had not kept music files on it (though I had tried music out on the iPod Touch as well).

One big issue that I faced was that iTunes, which I recently installed on my recently upgraded desktop computer, did not have this music set in its Library. I would have to load (import) that set into iTunes. But my disk backup of audio had some more music and other audio files. What was on the iPod Nano was a selection of this music on disk backup. I needed to get the music set from my iPod Nano onto my newly installed iTunes library. But iTunes did not permit direct copying of music files from iPodNano to iTunes library! It allowed only for music to be imported into its library from computer disk or by buying from its Music store.

I should also mention that I did not seriously explore the option of importing old iTunes installation library export files on my backup devices. These export files would have been made prior to Mahasamadhi (April 2011). In the over six years that have passed, my computer hard disks have got re-organized somewhat. Further I now primarily use a 60 GB Solid State Disk for my desktop computer and try to keep my stuff largely on the Internet, and have retired/disconnected other old (electro-mechanical) hard disks as they seem to give some problems. For more disk space needs I prefer to use my USB external (backup) drives - a Seagate GoFlex 2 TB drive and a Western Digital Passport 1 TB drive. ... So the 6 year or older iTunes export files would not have the correct directory mapping to the music files now on my desktop computer. That would have, in all probability, needed some XML export file patching, which I did not want to get into.

Browsing the net for ways to transfer music files from iPod Nano to iTunes library, and tinkering around with third party programs provided me the solution. Essentially I copied iPod Nano music files from its hidden folders to computer disk using Windows copy. The file names were anonymous. Tinkering around with a third party software putting these files on the iPod Touch and then exporting it back to disk, got me a single directory with proper file names (file names were typically the song titles).

I was then able to import these music files into iTunes library. And iTunes picked up most of the tag information like Artist, Album and Genre from the files.

But there were two outstanding issues. One was that iTunes did not pick up the Rating (tag) from the files. The other was that smart playlists from the iPodNano had to be copied/transferred into the iTunes library.

I solved the Rating problem by using a third party program which synchronized ratings from Windows Media Player (WMP) to iTunes. First I had to import the music set into WMP - that was quite straightforward. But then there was a stumble as some Ratings were picked up as 4.75 stars, whereas my smart playlists expected the ratings to be 4 or 5 stars, and my iPod Nano music set had 4 or 5 stars as its rating values. All such ratings (4.75 stars) had to be changed to 5 stars which I did manually in WMP, but it was quite easy to do and did not take much time. The manual operation also gave me some idea of the files whose ratings I was changing (at rapid speed by simply mouse-clicking on the 5th star for the bunch of 4.75 entries). Once the Ratings were fixed in WMP, the ratings synchronization/copy from WMP to iTunes using the 3rd party program was straightforward. So I got the iTunes Library music files with same ratings as on the iPodNano.

The smart playlists (around 34 in number) copying was more tricky to resolve. Copying (drag-and-drop) from iPodNano to iTunes (or to iPod Touch) failed. I had to save each smart playlist from the iPod Nano, using iTunes Save Playlist command, as XML format file. Text file format does not export the smart playlist rules. XML format file exports both rules and individual song entries that match the rules. Next step was to import this XML playlist file into iTunes (Library). Once the smart playlist was in iTunes (Library), I could copy it (using drag-and-drop) from iTunes (Library) to iPod Touch. It was a laborious process to do this for all the around 35 smart playlists but was a safer method as compared to any XML export file patching/hacking work.

Eventually my iPod Touch 2nd Gen had the same set of music including smart playlists as my ipod Nano 4th Gen. In the process, my iTunes library too has imported this set of music including the smart playlists.

Given below is a detailed log of the process. Readers not interested in such details may please skip reading the rest of this post.

Detailed Log

My ipod Nano is 4th Generation as its Model number is A1285, see https://support.apple.com/en-in/HT204217.
User Guide of ipod Nano is available here: https://manuals.info.apple.com/MANUALS/0/MA629/en_US/iPod_nano_4th_gen_UserGuide.pdf
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The ipod Nano was loaded with a lot of music (whereas the ipod Touch had no music on it), and some photos. Made a copy of the entire ipod Nano file system including hidden folders into 2 TB Seagate GoFlex external USB drive, in a folder named, "ipod-Nano-Full-Backup-Sept-2017".

There seems to be some manual though complicated way of extracting the music files from the anonymous names with which iPod stores it.

Could not get a free app so far that is able to copy all the music from the ipod as originally named mp3 files into the PC. Hope to do some more searching for it. Eventually I would like to make a copy of all this music on my ipod Touch too. Both my Nano and Touch are 8 GB devices. The hidden music folders & files size on the ipod Nano, is reported as 4.34 GB in Windows File explorer.
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Using Syncios free version to import music from ipod Nano full data backup's ipod_Control/Music sub-folders as given below, into ipod Touch. I read this article: http://www.syncios.com/how-to-backup-ipod-music-to-computer.html which gave the impression that I could backup ipod (Nano/Touch) music, using Syncios free version (see section: "Solution 2: Syncios iPod to PC transfer | File Size: 62.9 MB"), to computer. But after installation, I found that the free version does not allow that! However, it seemed to allow adding/importing music files/folders into ipod Touch device for free. So I tried to pick up the music from the ipod Data backup. While the file name that is added is the anonymous one, the other information shown on Syncios like Name (of the song), Artist, Album, Time and Size seem to be proper ones (as would be shown in iTunes for the original music collection).

Copied all the sub-folders F00 to F13 (14 sub-folders) of Music folder. Syncios application shows message at the bottom of its window, "Total:958 audio/video file(s), Total duration: 74:21:34", Total size: 4.33 GB". Looking at the video folder of ipod Touch in Syncios application shows "No video, "... So this 4.33 GB is what was copied in this process captured in above log.
[As the above process was going on, it struck me that I probably could have tried adding the entire ipod_Control/Music folder instead of its subfolders individually. Maybe next time I need to do this process I could try that first.]
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Thought about copying the photos (in .ithmb format) after conversion using some free tool somewhere from ipod Nano full data backup directory, into ipod Touch. But then I thought that it would be better to locate original pics (of higher resolution) from GoFlex backup data and load it into ipod Touch. I could also load some videos. So I could do a new selection of pics and videos, and consider the Nano pics as suggestions.
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I was disappointed to see that when I plugged out the ipod Touch and checked out its music, it showed no music data/files! I plugged it back in and saw whether Syncios sees the music data/files. It did. Saw an Export option. Decided to try that out. It did a great job! Now all the music is in one directory, "ipod-Nano-Music-Full-Backup-Sept-2017" on the Seagate GoFlex external 2 TB drive, WITH song title as the filename! All the other data like artist, album, genre (which I used as a multiple tag mechanism to act as input for smart playlists in iTunes) and even rating (shown in properties dialog and which was another input for smart playlists) seem to have been copied.

I had wanted one such flat directory of the selected 4.3 odd GB music files which were on the iPod. The full music on the external drive is too big to copy either to the user data part (30 to 40 GB totally) of solid state 60 GB system drive OR to copy to the 8 GB ipod Nano and Touch.

I have still to get this music onto the ipod Touch in a manner which is recognized by ipod Touch device. But I think I have got closer to that goal now.

iTunes application shows the music on the ipod Touch! Hmm. Why is ipod Touch not seeing it? Let me try restart of the ipod Touch.

Even without restart when I unplugged the ipod Touch again (from USB port), it listed the songs this time around! But attempting to play the song resulted in failure, with the play screen with song closing and coming back to song list! So addition of music from Syncios on ipod Touch is not working properly! Hmm.

I then tried deleting one song from device through iTunes (after reconnecting device to comp) and then added that file alone from GoFlex backup (with filename being song title name as created by Syncios Export). Once that got added I then dragged and dropped it from iTunes library to Music folder of ipod Touch device (on iTunes application). Then (without disconnecting from USB port) I searched for that song on the ipod Touch (it gave a message of updating music or something like that when I "unlocked" it), and played it. This time it played properly! Then I tried another song. That failed to play!

So one clear solution is to delete all music files from device and then import the entire 4.34 GB of music files into iTunes library from "ipod-Nano-Music-Full-Backup-Sept-2017" on the Seagate GoFlex external 2 TB drive. And then copy all these music files (4.34 GB total size) from iTunes library into iPod Touch.

After some hiccups, managed to do the process. [The copying broke towards the end, with Syncios (or some other ipod/iTouch app popping up and the ipod Touch getting disconnected in the process. The Huawei dongle Jio Internet connection also broke! I decided to uninstall all non iTunes apps related to iPod/iTouch device to ensure no interference. Reconnecting ipod Touch after that and attempting to copy all files from library to device automatically skipped the files that were already on the device. So it copied only those files that had not got copied earlier.] Now ipod Touch has 958 songs taking up 4.34 GB of space (which matches number of audio files and size of folder "ipod-Nano-Music-Full-Backup-Sept-2017"). Checked out a few songs at random on the ipod Touch and they are playing fine.

Surprisingly, free space on 60 GB SSD computer drive is 25.9 GB. So the music files being loaded into iTunes library did not duplicate the data! That's good. If I recall correctly, this is an improvement from what iTunes did 6 or so years ago which was when I used it for such stuff earlier (before Mahasamadhi of Bhagavan in April 2011). Then I think it duplicated the data in its (iTunes) folders on the computer (not Internet/cloud).
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Getting song ratings imported from computer disk music collection into iTunes

iTunes import did not pick up ratings from music files on Windows hard disk backup.

From this link, Synchronize music ratings between iTunes and Windows Explorer, https://superuser.com/questions/325402/synchronize-music-ratings-between-itunes-and-windows-explorer, I got the suggestion of using Music Bridge to solve the problem.

I downloaded the program and ran it. It provided a simple interface to do synchronizing of ratings alone (and other options) from WMP (Windows Media Player) to iTunes (or the other way).

Importing music files info. into WMP from GoFlex backup directory having all mp3 files in one directory (with ratings info. in the files) did not take long. Neither did it take up too much space. So WMP does not seem to make any copies of the mp3 files.

One hiccup was that WMP showed some files as 4.75 stars! That tripped up the first ratings sync from WMP to iTunes.

Manually fixed upgrading 4.75 star music files in WMP to 5 stars. It did not take too long but now I am more familiar with the WMP interface and I think that select of all 4.75 files from a rating wise sorted list and then edit rating would have done the trick. The edit command with mouse right-click should be done on the rating column.

Some music files were less that 4 stars (5 or 6 files) on WMP! Checked their rating on ipod Nano and changed it appropriately. Perhaps I mixed up ratings of one or two files from 4 star to 5 star or vice-versa while doing the manual Rating change work.

Then did a sync of rating back from WMP to iTunes. This time it did the job. Now on iTunes the smart playlist for 4 Star rating has 506 songs, and the smart playlist for 5 Star rating has 452 songs, accounting for the total 958 songs.

Plan to check with iPod Nano loaded into iTunes to see which two files ratings are different as I think the iPod Nano has 504 4 star songs and 454 5 star songs or something like that.

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Got the two wrong rating entries and corrected them.

Now 4Star songs are 504, and 5Star songs are 454 in iTunes Library as well as ipod Nano.
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Now copying (overwriting perhaps) songs from iTunes Library to iPodTouch, updates the ratings (4 star or 5 star) on iPodTouch! Have copied/updated all songs starting with A. Plan to do update in steps, starting alphabet wise.

Finished the copying. Then copied two smart playlists (newly created to help in this process) for 4 star rating and 5 star rating respectively, from All Playlists (which I think applies to iTunes Library), to iPodTouch. Now the iPodTouch 4StarRatingPL shows 504 songs and the 5StarRatingPL shows 454 songs. That's as expected.
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30th Sept. 2017, Exporting smart playlists into hard disk; importing smart playlists into iPods (including devices other than original device which exported the smart playlist).

The following extract by a "Mark Miller" on https://apple.stackexchange.com/questions/3537/exporting-itunes-smart-playlist-definitions gave me the pointer to the solution.

After rebuilding my SmartLists for the seemingly 100th time, I had to find a better way. I came up with a solution, but it takes some pre-planning - you have to export your lists as XML before you lose them. I then remove all song references from the XML file so the file only contains the SmartList parameters. Then when I need to restore the list (like after an update/upgrade), I simply import the XML file. Here are the instructions to save copies of your lists:

* Right-click on your SmartList and choose Export, then be sure to select XML as Save As Filetype.
* Open the .XML file with a text editor and search for <key>Playlists</key>. Set the cursor at the beginning of that line, then use your slide-bar to scroll all the way to the top. Select all lines from where you started up to the line that has <key>Tracks</key> , then delete those lines.
* Look for the line with <key>Playlist Items</key> . Skip the next line ( </dict> ), then click at the beginning of the next line. Scroll to the bottom of the file, then select all lines down to the third line from the bottom ( </array> ). Remove those lines.

Doing this reduces the XML file size (2k to 3k depending on the complexity of your list), and stores only the parameters of your SmartList, not the actual songs list. Importing these XML files will rebuild your song list, and this hasn't failed me yet. Remember to include these files with your backups so that you can recover these lists if your hard drive fails. Also remember to repeat the process if you ever change the parameters of your SmartList.

--- end extract from stackexchange.com ---

Ravi: The key learning for me from the above description was that exporting the smart playlist as XML file (instead of default text file), saved the rules in it. I tried the simple steps of exporting a smart playlist (BhagwanGr) from iPodNano to computer disk as XML file. Then I imported it into iTunes which resulted in the smart playlist being listed in All Playlists at the bottom of the left pane (which I think applies to the iTunes library). It showed up as a smart playlist and edit rules showed the rules! Next step was to simply copy the imported smart playlist from All Playlists into iPodTouch. That went through! Now I had the smart playlist on the iPodTouch with its edit rules showing the rules! Note that I did not do editing of the XML file as described in above extract of stackexchange.com article.

Another point is that I was able to connect both iPodNano and iPodTouch using two separate cable connections to two USB ports, and view both of them simultaneously in iTunes. Direct copy of smart playlist from iPodNano to All Playlists or to iPodTouch fails!!! But as described above, export of (particular) smart playlist from iPod device (Nano in my case) to computer AS XML FILE, followed by import of the XML exported file adds the smart playlist to All Playlists. From All Playlists one can copy the smart playlist onto other iPod devices (iPodTouch in my case).

Plan to repeat the procedure mentioned above for all the other smart playlists on ipodNano.

Finished the procedure. So now all the smart playlists from ipodNano are on ipodTouch (as well as on iTunes All Playlists).
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[I thank Mark Miller and stackexchange.com and have presumed that they will not have any objections to me sharing the above short extract from their website on this post which is freely viewable by all, and does not have any financial profit motive whatsoever.]

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