Moved the XML to it’s own folder that plex does not look at.
updated AGENT file path IN plex, and restarted the server.
Working on fixing the %20 for file location key ONLY in the XML file.
I figured out one way, when I get a free moment from work I will write here, at length, what I learned in the hopes of helping others.
You think so? I thought it might be helpful to some weary traveler who ends up in my shoes, and just can’t find ONE location to have a pathway that works for them. I know you guys don’t need the information, but I have to share, it was not easy to figure out, even the simplest thing, such as playlists cannot be in folders in your itunes library, otherwise, plex cannot see them when importing. Just a couple of pointers to help less initiated along.
Either way, I truly can’t thank you enough for helping me and providing pointers, couldn’t have done it without you. 
Then, even more thanks are in order.
I’m so surprised there haven’t been more. On our road to killing Itunes, I think more shall follow…
If anyone comes across this and doesn’t have the good fortune of connecting with trumpy81, feel free to reach out and I’ll see if I can do anything to help. 
If trump81 can point to the various instructions on how to do what dahmooser has covered, I would greatly appreciate it. Or, if dahmooser can post his findings on this exchange, that would be greatly appreciated. I am in the exact same situation he is in. I have been trying to get iTunes/importing of playlists accomplished for well over 8 months to no avail. I have tried everything.
Once simple question additionally, why do you need to remove the %20 for file location key ONLY? And do you remove both %20 in the file location for the XML when edit the file?
I would really appreciate the help and detailed instructions dahmooser! You’d be a lifesaver.
And trumpy81, can you confirm with 100% assurance that the playlist import has returned per your post?
Try installing version 1.23.5.4801 from Plex Downloads .
The Import from iTunes option has returned!
Thanks!
Thanks for clarifying that. So is this for every single song that this needs to be done? That’s quite the task with over 14,000 songs. Or is there something in the XML file that can be edited once? And if it’s for every song, is there a quick method that can run (script?) that can do it for me?
So you are confirming that the latest Plex Pass version has the iTunes import playlist option back?
Thanks.
What I can do is delete all the smart playlists and then paste the updated XML onto the NAS. I don’t use those really anyway. They’re more a starting off point for some playlists I create if you follow. So those can easily be deleted.
Can you explain why Plex can’t read the XML if it has these %20 within the XML for each song? I have 15,000 tracks so this will be a mountain of work. Seems like - if Plex had the import iTunes playlists feature - that it would work without the user having to modify that file on the back-end. I know how to edit and do the replacements but in looking at the file, you indicated to only do it on the file path? If I do “find and replace” (do replace All for example), it sees every single %20 so there must be an easier way?
I guess the larger question is why Plex has this feature without some indication to users to do this. I’ve gone into the forums and see this described, but certainly Plex wouldn’t expect users to do this would they? And if I do some updating on my itunes library and then update the XML, it sounds as though I would have to go into that XML each and every time I do something in iTunes and then update the XML all over again?
One more question, does it matter if I open Plex up via Synology or the web? My login credentials are the same.
I noticed when I was trying to update Plex via Synology login method, it saved an SPK file. Looks like I need to open that through Synology:
Open DSM Package Center > Manual Install (top right of window), click on browse and navigate to the .spk package in your downloads folder, select it, click on open and continue, following the prompts.
If I install the update while logged in via the web, will it download an .exe file? And does it matter which method updates Plex? I realize, per your comment in your post to someone on June 17 that you should keep Plex updated within Synology, but I’m just asking the question as a general rule for going forward?
Also, thanks for confirming that the import playlist option is now available again. 
And on the XML file, do you mean you also want me to remove the Localhost from each song, along with each %20?
file://localhost//volume1/music1/Al%20Green/Let’s%20Stay%20Together/Al%20Green%20-%20Let’s%20Stay%20Together.m4a
And while covered earlier, could save time if you could take the example above and paste how it should look. Use underscore _ to indicate a space?
I’d sure appreciate it.
Thanks.
Haven’t done anything until I hear back (hopefully) but as I’ve read more forum comments on playlists…
Trumpy81 said: You need to replace the spaces in the file path with %20, NOT remove them.
Me: On my XML file right now, each individual song has this %20 so I leave those alone. I have not removed those. I did delete the dozen or so Smart playlists I have as I don’t really use them anyway, so the updated XML does not contain them.
I’ve seen some conflicting things on how to modify the XML in further needs.
Let me use this song as an example:
Locationfile://localhost//volume1/music1/Queen/News%20of%20the%20World/Queen%20-%20We%20Are%20The%20Champions.m4a
Do I remove “localhost”? I see some saying I should, but others say I shouldn’t. So if the song file has the %20 (representing spaces), I don’t do anything, right? And if I don’t need to remove LocalHost then is there anything I need to do with each of the songs that resemble this same layout.
I’m using Synology and am still on version 6.
I’ll await your replies to this and my other posts late Friday. Thanks!
And I’m a bit confused on that post where you say
You do NOT replace ALL spaces in the .xml file with %20, only in the file path.
Is the song the “file path” - meaning the song example (Queen) that I just showed? And if so, it seems you’re saying I should remove them? So sorry, just confused and want to make sure I do things right.
So “localhost” stays, I don’t need to remove those from each song, right? And also leave the %20 in the Location line for each song, right?
When you say “you only need to work on the file and folder paths”, are you saying there’s something in the Music Folder that I need to do something to? My XML file shows only one line in the code for this:
Music Folderstring>file://localhost//volume1/Music1/
The “volume1/Music1” is the correct location for the songs on my NAS. So is there anything I need to do with the string above which is from my XML file?
(I did notice that “Music” is capitalized here on the line of code above but for each song in the XML the “music1” is lower-case. Does that matter? I’d read something that they need to be the same?)
And inside of Plex, for the iTunes plug-in for XML library path, I would put the location where the XML file is on my Synology - unrelated to the path inside the XML, correct? I read that you want to put the XML file in a folder that is NOT on the same location as the song folders (Artist/Album). So in my case, that would be;
volume1/home/itunesXML
(I created a folder in the Synology “home” folder called “iTunesXML” and the file is inside that folder. Or should I just paste the XML in the home folder without a separate folder for it if you follow?)
I don’t have to remove smart playlists as I already deleted the dozen or so I had. I only use smart playlists to create some various playlists, then create a folder manually inside of iTunes and drag the songs from the smart playlist to the new manually created playlist. So that shouldn’t be an issue.
Please let me know and I’ll get to work on this. Thank you so much!!!
One other question, I have a number of playlists that have various special characters in them. Some examples:
-pre-1984 1 rating
#1 songs on the charts (I-TOUCH)
1967-79 (4-5*)(Am/CR)
A 4-Rating
AAA-SUMMER !!! redone mixing bunch
AM Pop (63-71) 4 &5
Beatles-/*****
Do I need to change these so that no characters like parentheses, asterisks, ampersands, exclamation marks, dashes, slashes or # and so forth aren’t used for naming of the playlists, or will Plex be okay with those? I would have to do a LOT of work to modify those but if it gets to the desired outcome, I’ll do it.
Please let me know. THANKS!
One point of clarification for me - is the Music Folder path you put in your reply related to the where the “music” is on the NAS (and thus where each song is), or does it have to do with where the XML file is located that I put on the NAS (copied it and pasted it onto the “Home” folder per my input a short time ago)? I just want to make sure I am doing the right thing here.
The XML already shows the path for each song I think, right? E.g.
Locationstring>file://localhost//volume1/music1/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a File Folder Count4
So I just want to make sure I put in the right Music Folder link. As pasted earlier, on my XML file that shows as:
Music Folderfile://localhost//volume1/Music1/
In other words, do I keep it like this, or change to …"//volume1/home/…?
Thanks!
For those seeking more information, here is what worked for me, I hope it helps in some way. One thing I will add - you may get an error message when importing. Before attempting to import again, go see if your playlists are imported. Mine were, but, I had imported TWICE (thinking I made mistake) so I had to go and delete all of the duplicate playlists.
Ah, and another caveat. I learned that playlists cannot be in FOLDERS IN itunes. In other words, within the Itunes application, you should NOT nest/organize your playlists in folders as I did (1980s /U2 Favorites). Plex (currently doesn’t seem to recognize these in the Itunes XML file it generates that you will be altering.
I was unable to find this exact file version. I did download two updates on Friday after reading this forum and your post but neither were this exact version. The closest one I had was Version 1.23.6.4881.
I manually installed that update on my Synology for Plex and then also put a new location in for my XML file on the Synology which for me is:
/volume1/iTunesXML/iTunes Library.xml
This folder is outside of where the music files reside.
After updating that in Plex, I saved it. I then restarted my NAS. I opened Plex again but all I am seeing when I click the three dots next to playlist is “Pin”. There is no “import iTunes playlist” option.
I did not alter the XML file because the two areas already show:
Music Folderfile://localhost//volume1/Music1/
And each song already shows this:
file://localhost//volume1/music1/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a
If I am supposed to remove all these %20 for each song, then confirm please because I saw in the forum that I was supposed to leave those alone.
Perhaps my flow of things is what is not allowing the playlist import to not show. I realized that I had not imported the updated iTunes library of music (which matches this XML) yet as I was awaiting the updated input so I am not in the process of doing so. That will take quite a while, but that shouldn’t change the fact that I should be able to see the import iTunes playlists next to the Playlist on the left navigation pane should it?
I have two servers in Plex. One is my desktop (where I’ve imported some hi-res music files) and then the Synology DS720 Music library one, which is the main one. HOWEVER, that one was the original music library from iTunes which is mapped to my Y drive. I just am adding the final library which should point to the NAS proper, per my XML. So on the NAS, I have two music folders that are iTunes music ones. (I also have a few other music folders unrelated to iTunes).
In Plex, I was thinking, since my XML is pointing to /volume1/music1 folder on the NAS, should I rename my friendly server name to /volume1 instead of DS720? I noticed that that’s the friendly name I gave it. I’m not sure how all that works.
I’m trying everything I can to get my itunes playlists imported.
In summation:
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I am adding the music library now that points to /volume1/music1 (and XML song-by-song matches that (e.g.)
file://localhost//volume1/music1/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a -
I have put the XML path as the /volume1/iTunesXML/iTunes Library.xml.
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I did not alter the XML file as I was told not to remove the %20 in the name of each song file, so if this is wrong, please clarify. And the Music Library is pointed to the right location on the NAS.
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I updated the software to the closest version I could to what was indicated in this exchange that announced iTunes importing of playlists was back. If this has been removed again, can I get the exact version that had this?
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Again, I have two servers inside Plex. One is my desktop computer where I’ve added some hi-res music folders and my DS720 (friendly name). And on that I have a MUSIC/MUSIC folder that is mapped to my Y drive but is on the NAS. And I am importing the MUSIC1 folder which XML should match song-to-song.
Regardless, no matter, shouldn’t I be seeing the Import iTunes playlists when I click the three dots?
Please advise. I am very hopeful you can help me. Thanks!
I updated my Synology to a version of Plex - 1.23.6.4881 - which is not the version you recommended three days ago but they wouldn’t have removed the iTunes importing playlist option right away would they?
I did a system restore setting in Windows so perhaps I could roll it back (though I’m not sure that would roll it back on Synology).
I’m hoping that I don’t have to roll it back. Is there a more recent update that has it? I did see a newer version but wanted to stay as close as I could to the one you said the playlist import had returned on.
You did confirm that the import iTunes playlist was back so wouldn’t it be on the most recent version as well? What am I doing wrong where all I see is “Pin”?
I just wonder if this is an issue with the NAS, where it has to have some relation to Windows (mapped drive, or Plex using a desktop computer). I just can’t figure it out.
Also - I do have a library that is mapped to my Y drive, but the XML file for that library shows this:
file://localhost/Y:/MUSIC/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a
But that song in Plex has “volume1/Music/Music” so my Apple guru said the reason playlists don’t work is because XML has to match Plex file structure. He doesn’t know Plex much he says. This is why I created a whole new library where the song path file in itunes is actually “volume1\music1\Beatles - Hey Jude” for example so that this matches what would show in the file path inside Plex.
Again, regardless, I should still see the Playlist import option and it’s not there. You said it was or you wouldn’t have said that so I’m at a complete loss here.
Please advise. Thanks.
My sincere apologies if you feel you’re answering the same questions over and over.
Let me step back and hopefully ask a differently.
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The version you referenced had import iTunes playlists is not available that I can find. The version I installed is: 1.23.6.4881. So should that version have this option? If so, any thoughts as to why it’s not showing up for me? If not, how can I get the right version? And can Plex on Synology install an older version?
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I’ve pretty certain that I’ve done everything as you instructed. I deleted all smart playlists from iTunes so the updated XML contains none of them.
In my XML I have:
Music Folderfile://localhost//volume1/Music1/
For each song, I have left the %20 and did not update those at all.
Locationfile://localhost//volume1/music1/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a -
My XML file is on my Synology in a completely different folder than the music files. The XML path in Plex is: /volume1/iTunesXML/iTunes Library.xml
-
My song files in the XML match what is showing on Plex (sans the %20) for the song path such as: /volume1/Music1/Alicia Keys/Songs in A Minor/Alicia Keys - Fallin’.m4a
That song in my XML is: file://localhost//volume1/music1/Alicia%20Keys/Songs%20in%20A%20Minor/Alicia%20Keys%20-%20Fallin’.m4a
My iTunes library is version 10.7. I do not have the latest software installed because I frankly hate any newer version so I don’t have the checkbox that says something like “share XML with other devices” or whatever. But that shouldn’t matter.
If I have everything as you’ve instructed, and with what I’ve provided above, what could I possibly be doing wrong? I sincerely don’t mean to be redundant but I must be doing something wrong and I just can’t figure out what it is.
One thing I think I already covered was that I have two music libraries on Plex that are on my NAS. Could they be conflicting with each other? The earlier library has a different XML library folder and the music in the XML points to a mapped drive:
Music Folderfile://localhost//DS720/music/
And the individual songs are such as:
file://localhost/Y:/MUSIC/Beach%20Boys/Little%20Duece%20Coupe/Beach%20Boys%20-%20409.m4a
So could that be causing some issues within Plex?
I’m hoping to get this figured out and deeply appreciate your help.
Bubba,
Here is some more information for you, though I cannot answer most of your questions/they are beyond my level of knowledge as I was successful in importing my playlists.
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I had two plex servers running, one on a Drobo atttached to an Imac, then at the same time, the one on my synology. They both ran perfectly, and I did this import while the Drobo one was still connected (i’ve since turned that one off).
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I don’t think, after Trumpy81 et al. helped address my issues that they would then go and remove that functionality. I cannot be certain, but I find this highly unlikely.
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My success seems to have arisen from cloning all the data files that itunes creates, pointing plex to them and altering that ONE XML file in the cloned version to reflect the proper file path of the Synology. (note that I only cloned them because I wanted to keep the itunes files unaltered, it was not a necessity, only a way to go back if I messed something up).
I wish I could be of more help.
I’m not trying to waste everyone’s time. I’m simply trying really hard to figure this out. Could you look at this at least and let me know.
Are either of these paths incorrect? Should I only have one forward slash after localhost? I just noticed upon closer examination that in your example to follow, you only have one:
Locationfile://localhost/volume1
Music Folderfile://localhost/volume1
My XML shows:
Music Folderfile://localhost//volume1/Music1/
Locationfile://localhost//volume1/music1/
Could this be as simple as the one forward slash that’s in my path?
If so, I’ll change it out. And if so, would this be preventing Plex from showing the “import iTunes playlists” when you click the three little circles next to playlist on the left navigation?
I can’t imagine why Plex wouldn’t show this even if this were wrong, but I’ll give it a shot. I do have the updated version so if the forward slash doesn’t matter, then I’m at a loss as to why I’m not seeing the feature with the update I did in Plex. I wasn’t accusing Plex of removing the feature, but it is bewildering as to why it’s not on my version that I just updated.
Thanks.
