Requesting Definitive Answers on How to Import an iTunes Playlist into Windows PMS

Plex Media Server Desktops & Laptops
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My scenario:

Plex Media Server for Windows 1.13.5.5332-21ab172de
iTunes 12.8.0.150
Windows 10, v1803 with all the latest Windows updates

My iTunes library is NOT located in the default location. I have a separate drive for all media (movies, music, TV shows, etc.) and so my iTunes Library is located on E:\iTunes

In iTunes I have several playlists, all created by me (there are no Smart playlists).
Playlists are NOT located in any folders. In other words, in iTunes, under “Music Playlists”, all my playlists appear directly here and there are no playlist folders present.
ALL music in iTunes is DRM free. There is not a single track with DRM.

In iTunes I have enabled the option Edit > Preferences > Advanced > Share iTunes Library XML with other applications.

In Plex I have configured the following settings:

Settings > Server > Plugins
“Enable iTunes channel” is selected
“iTunes library XML path” is set to
e:\iTunes\iTunes Library.xml < As noted below, I have tried to specify this both enclosed in quotes and without quotes.

After setting the above, PMS was stopped and restarted.

When I created my music library in Plex, I pointed it to my iTunes Library which is located on e:\iTunes. There was an option to import playlists from iTunes which I selected.

After creating my music library in Plex, all my music is present but I see no playlists.

Question #1: I have seen various discussions saying that the iTunes library XML path should be enclosed in quotes and some saying that it should not. Which is correct?

Question #2: If I make any changes, for example, I add or remove quotes to the iTunes library XML path, how can I get Plex to look for playlists again? When I edit the settings for my music library there is no option to import playlists. It appears that this option appears only at the time of the initial library creation. Is it as simple as selecting “Scan Library Files” for my music library or do I need to completely recreate my music library in Plex and wait for many hours for it to complete? As another possibility, would “Refresh All Metadata” work or is this even necessary?

Question #3: Are there any other settings I have not listed for either PMS or iTunes that I need to check?

Question #4: Let’s assume that we get this working somehow. If I create any new playlists in iTunes at a later time, how do I get Plex to recognize or see the newly created playlists, or should this process be automatic?

Any answers would certainly be appreciated. This is my last hurdle to a perfect Plex configuration but I’ve been spending many hours trying to figure out this one issue.

1 Like
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My iTunes library is NOT located in the default location.

That’s fine as long as iTunes itself is installed in the default program folder.

1 - “iTunes library XML path” is set to. You need the path to the file, not the file itself. No quotes needed.

2 - I need to double check but once you have the library setup, when viewing your library from Web (where you can see all the artist), there is the … menu to the top right, click it, there should be an option there to import from iTunes again. Note that importing is a 1 time thing, it does not sync back to iTunes. If you make changes to iTunes, you need to import again. If you make changes in Plex, these cannot be sent to iTunes.

3

Thanks for the response, it is very much appreciated.

The only kink at this point is that I cannot find an option anywhere to import from iTunes again.

I’m using the web client (tried within Server as well), and am in the view where I can see all my music artists. I am looking at all the menu options in the upper right of the screen. Maybe I’m overlooking it somehow, but nowhere do I see any option to attempt an import of the iTunes playlists again.

4

MovieFan.Plex,

Your suggestions have partially helped me but also brought up new questions.

First, an update on the status…

Your response to my initial question revealed that I had incorrectly specified the path to the iTunes XML file by including the file name in the path. I corrected this. I then had updated this thread by responding that I still could not find any option to try and re-import the playlists. After waiting for a response for over a day to see if anyone could tell me where to find the import playlist option, I finally decided to bite the bullet and simply delete and recreate my entire music library. The good news is that this worked! I now have my playlists.

However, oddly enough, when I go back into settings and look at the “iTunes library XML path”, Plex has updated the path and added the filename to the path.

I also noticed that at the very end of importing back in my entire music library, iTunes was automatically launched on my computer. I had read in a previous post that it will only open iTunes if it cannot find the XML file properly.

As a test I Finally, I changed the path to the XML file back to the path without the file name and restarted Plex. This causes the field with the path to completely disappear from the GUI after restarting Plex.

So then, I have 3 remaining questions:

  1. Where can I find the option to re-import my playlists? I still have not been able to locate this. If I create new playlists in iTunes I’d like to be able to re-import these without having to re-import the entire music library :slight_smile:

  2. Will the fact that Plex added the filename to the path cause me any problems in future re-imports of playlists? If I knew how to re-import playlists again I guess I could answer this one for myself after testing it, but since I can’t find that option I thought that I would ask.

  3. As noted, I changed the path back to just the path without the filename and restarted Plex. Now, the option for a path to the iTunes XML is completely gone. No such field even exists any longer. How can I get it back?

5

For the benefit of those who might be following this thread, I just want to summarize what I learned to this point which has allowed me to successfully import iTunes playlists into Plex Server for Windows.

To import your iTunes playlists, do the following BEFORE you import all of your music into Plex:

First, iTunes needs to be installed to the default location but your iTunes library can be located elsewhere if you wish.

You need to enable iTunes creation of an XML file that can be used by third party applications. To do this, open iTunes and select the following:

Edit > Preferences > Advanced

Check the box called “Share iTunes Library XML with other applications”.

You can now close iTunes.

Now, in Plex Server for Windows, do the following:

Go to Settings > Server > Plugins

Check the box for “Enable iTunes channel”.

In the field “iTunes library XML path” specify the full path to the iTunes library XML. Do NOT enclose the path in quotes and do NOT specify the file name itself in the path.

Note: The XML file should reside in the root of the iTunes directory. For example, in my case, my iTunes Library is located in E:\iTunes. There I see the file “iTunes Library.xml”. So I would specify “E:\iTunes” (without the quotes!) as the path.

A restart of Plex Server is required at this point so stop the server and restart it now.

At this point, you can import your music library. Create a new Music library in Plex Server. As you are creating the library, you will have 4 sections on the “Add Library” screen. On the “Advanced” tab, make sure that you select the checkbox called “Import from iTunes”.

If you have a large library, it may take a long time to import all your music. The playlists will be imported all the way at the end of the process.

Still to be Determined

The above process is a one-shot deal. If you ever modify a playlist in iTunes or create new playlists there, I have no idea how you would get Plex to import the playlists again. From all that I can see, it appears that you would have to re-import your entire music library all over again as I simply cannot find an option anywhere to re-import just the playlists. Since I’m not getting any further responses on this thread, I am going to create another thread just to ask if there is a way to re-import playlists after the music library has already been created in Plex. If I get a response that I can verify as working, I’ll update this thread.

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Sorry for not providing an update. I’m still looking into this. There is suppose to be an option to re-import playlists from iTunes.

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No worries :-).

Thanks for letting me know that you are looking into it. It’s the one, tiny item I have left to having the perfect media server for me.

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Look in Plex Web to the right of the “Playlist” category do you see the “…” menu. Try that.

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To the right of the “Playlists” category I see no “…” menu. There is a “…” menu to the right of Music, Movies, etc. but nothing at all to the right of Playlists.

This true for both Plex Web and Plex Server.

10

Just wondering if there are any updates to this. Can you at least confirm that you also do not see a “…” menu to the right of “playlists”? It would be nice to know if it’s just me seeing this.

Thanks!

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I have two Plex servers set up identically. One shows the menu to the right of the “Playlist”. For the other, you have to open the playlist and there is an asterisk in the upper right hand corner… clicking reveals the “import from itunes” selection. I have no idea why they are different… both are Win 10 PCs on same local network.

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Yeah, those are the 2 locations where the “import” option should be. I’m trying to verify which is correct. I believe it’s based on the version of Plex Web.

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Wow, that’s crazy. I have neither of those.

Clearly I must have setup everything correctly initially because it did the import when I created my music library. Only thing that I can think that might be different from the average user is that my iTunes music library itself is not in the default location and my Plex Data directory is also not in the standard location.

It’s certainly puzzling.

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Neither of those should matter. Can you verify what version of PMS and Plex Web you are using?

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Both are showing a version of 1.13.5.5332.

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Sorry, player is actually 2.19.0.902

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That’s not right. There was no Plex Web 2.19.0. I don’t think you are looking in the right place.

What browser are you using? Have you tried another browser to see if that is the issue.

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Yeah, the versioning is confusing. When you download it, it says that the version is 2.19.0.902 on the download page. In Plex Media Player > General it says 3.69.0.

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In answer to your other question, I have now tried Chrome, Edge, IE, all with the same results.

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Can you get me your PMS logs? PMS does a check to see if the itunes feature is working, if it doesn’t find it, then Web won’t show the import option.

Ah. That’s PMP. It has 2 versions, 1 for the desktop (web) version and one for the TV version.