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

Plex Media Server Desktops & Laptops
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TeknoJunky,

I intend no offense, but you keep suggesting things that I have clearly already stated that I have done earlier in this thread. Perhaps a review of earlier posts in the thread would be helpful :-).

Again, I intend no offense. I know it’s a long thread so let me summarize:

In brief, yes, I get a successful initial import every time now. That part works. It is after the initial import that there is no option anywhere to perform an import again.

I can reproduce this EVERY SINGLE TIME, even with a 100% clean, new install of Windows, Plex, and iTunes and NOTHING ELSE installed on the system. I now have a Virtual Machine setup for testing that has a new install and the entire iTunes library consists of only about 5 albums allowing me to create a new library in Plex very rapidly.

I’ve even tried several recent versions of Plex, all with the same results.

Still, I do appreciate your trying to make suggestions. However, at this point, especially since I can so easily reproduce this at will every single time, I think I really need further attention from someone at Plex.

42

yes clearly I needed to read your later replies more carefully, to be honest I started replying from earlier in the thread when you initially asked about the import/reimport, I skimmed through not seeing a clear explanation or picture.

I do remember having difficulties getting it to work early on, myself. But that was a year or more ago now, and I have slept since then, sorry.

If it is an issue, it must be something specific to windows, because it is working for me on linux.

And I obviously don’t have itunes installed on my linux nas server, only the xml file which I copied there from wherever I had my itunes library previously, so the specific installation of itunes is not necessary, the only thing required is the xml file. (at least on a non-windows box)

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ATTENTION PLEX: I HAVE SOME ANSWERS FOR YOU

So the whole problem that we have been chasing here in this long thread appears to be caused by the new iTunes 12.9. I can’t tell you if other recent versions are affected, but I was able to download a much older version of iTunes (12.4.3.1) and install it. Other than the version of iTunes, I have done nothing different and Plex will then display the “…” menu to the right of “Playlists” with that version of iTunes installed.

Please note that I can easily reproduce this issue at will, over and over, in a matter of minutes so I am now 100% confident that the version of iTunes is what is causing problems for Plex.

As noted in my earlier posts today, I have a Virtual Machine with snapshots so I can roll back to repeat this test over and over. Since my entire iTunes Test Library is made up of only 4 albums re-doing tests is REALLY fast.

If you need me to test anything or provide any other info I can do so very quickly!

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Thanks. I will let the team know and see if they have any ideas.

45

I have one additional piece of information and am working to learning more now.

It seems that the issue may possibly be with a fresh installation of iTunes 12.9 only. I just now installed iTunes 12.7.4 and verified that Plex was working fine with it. I then upgraded to iTunes 12.9 and the ability to import playlists continues to work. However, if I start off with a new iTunes installation of 12.9 (not an upgrade), that’s when Plex is not working.

I’m just trying a few things now like uninstalling iTunes 12.7.4 then installing 12.9 to see what happens if I already have an iTunes library that was previously created by another version of iTunes. I’ll report here what I find.

46

Thanks. That is very useful info.

47

Okay, the issue is now getting even more convoluted.

I noticed that there was a new version of Plex server available today (1.13.8.5395) so I downloaded it.

I took my test setup and installed iTunes 12.9 and that new version of Plex Server. It is working fine.

I upgraded my “Real” plex server to the new version of Plex and it’s still not working.

Testing continues.

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MAJOR UPDATE WITH A SOLUTION

Okay, I now have this issue solved. Here is a complete summary

Apple has started to distribute iTunes for Windows through the Microsoft Store. If you install iTunes through the Store, this is when the ability to import from iTunes breaks.

To be clear, if you create a new music library and choose to import from iTunes, this will work. However, after that initial import, you will NOT have the “…” menu to the right of “Playlists” in Plex which means that you cannot re-import playlists again from iTunes.

The trick is to go up to the Apple web site and download iTunes from there. Note that Apple tries to redirect you to the Microsoft store for iTunes now. To obtain it directly from Apple, do the following:

  1. Go to www.itunes.com.
    2)Click on the “Download” link.
  2. Do NOT click on the “Get it from Microsoft” button. Instead, scroll down to where it says

Looking for other versions?
MacOS > Windows >

Click on that “Windows” link.

  1. Scroll back up again and click on the “Download now (64-bit)” or “Download now (32-bit)” button.

On my personal Plex Server where imports were not working I was able to resolve the issue by doing the following:

  1. In Plex, go to settings > Plugins, and disable the iTunes plugin.
  2. Restart Plex
  3. Uninstall iTunes (This was the version installed via the Microsoft Store).
  4. Reinstall iTunes using the procedure above.

Note: If you have your iTunes Library in a non-default location, you may not see your library when you open iTunes after the re-install. To correct this, close iTunes, then reopen iTunes by holding down the “shift” key while double-clicking the iTunes icon. A dialog box opens asking you to create a library, choose a library, or quit. Select " Choose library…" and point it to your existing library.

  1. In iTunes select the “Edit” menu at the top of the screen, select preferences, go to the Advanced tab, make sure that “Share iTunes Library XML with other applications” is selected.
  2. Go back into Plex and re-enable the iTunes plugin.
  3. Restart Plex.

You should now have a “…” menu to the right of “Playlists”. Selecting that menu will give you an option to import from iTunes.

49

That does kind of make sense. Windows Store apps don’t work exactly the same as their regular apps so the link between PMS and the Store App could be broken. I’ll let the team know your finding. Thanks again for your work.

Edit - Thinking more, it really does make sense. The Store Apps are not installed in the regular “Programs” folder so PMS won’t think iTunes is installed there. I’m surprised the initial import works. The check must be done differently during the initial import versus just checking to decide whether or not to show that import option.

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Part of what is so confusing is that the store app looks just like the regular desktop version. It doesn’t look like your typical Modern UI / Windows Store app.

I had another thread in which I was posting step by step instructions for setting up support for iTunes in Plex because some people had confusion over little details such as whether to specify the library file name in the path, etc.

I’ll update that post so it can serve as a kind of step-by-step to anyone searching the forum for info on setting up iTunes playlist support.

Also, I’ll note how you can identify whether you have the version from the store or the regular desktop version installed.

I also just want to thank you for sticking with me during this entire process and looking at logs and such. Let your Engineers know that if they need anything more I can provide it quickly and easily.

I still have my VM where I can in a matter of minutes install the desktop version, create a sample library, and grab logs. I can then in a matter of minutes reinstall an identical setup with the Microsoft Store version of iTunes and get logs if needed.

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SUMMARY: Complete Guide to Importing Playlists From iTunes to Plex Server for Windows

For those following this thread, here is a complete summary of how to setup Plex and iTunes to allow for the importing of playlists from iTunes to Plex.

Currently, as of September 22, 2018, the version of iTunes installed from the Microsoft Store is not working properly with Plex. You may be able to do an initial import of the playlists from iTunes, but the option to perform future imports will not appear within Plex. I’ll address this further below.

iTunes should be installed in the default location, but the music library does not need to be in the default location.

Initial Preparation

If iTunes is not already installed, install it. If iTunes is already installed, you need to make sure that you have the desktop version installed, NOT the version from the Microsoft Store.

If you already have iTunes installed, determine the version installed by any one of these methods:

  1. Open iTunes. Select Help > About iTunes. Look at the version number. You will see something similar to one of these (Your version may be different):12.9.0.167 < This is the Windows Desktop version
    or
    12090.167.37085.0 < This is a Windows Store version
  2. In Windows, click on Start > Settings > Apps > Apps & Features. Locate iTunes in the list of apps and click on it. Under “iTunes”, if you see the words “Advanced Options” then you have the Windows Store version.
  3. In Windows Search, type in “iTunes”, without the quotes. It should find the iTunes app and say either “Desktop app” or “Trusted Microsoft Store app”.
  4. Open the Windows Store app and search for iTunes. When you find the app, there will be a button that says either “get” or “launch”. If it says “launch” then this implies that you already have the Windows Store version installed.

If you have determined that you have the Windows store version, uninstall it.

If you need to install the desktop version, do the following:

  1. Go to www.itunes.com.
  2. Click on the “Download” link.
  3. Do NOT click on the “Get it from Microsoft” button. Instead, scroll down to where it saysLooking for other versions?
    MacOS > Windows >Click on that “Windows” link.
  4. Scroll back up again and click on the “Download now (64-bit)” or “Download now (32-bit)” button.
  5. Install iTunes from the file you just downloaded.

Note: If you have your iTunes Library in a non-default location, you may not see your library when you open iTunes after the re-install. To correct this, close iTunes, then reopen iTunes by holding down the “shift” key while double-clicking the iTunes icon. A dialog box opens asking you to create a library, choose a library, or quit. Select " Choose library…" and point it to your existing library. The library file is usually in the root of your iTunes directory and is called “iTune Library.itl” by default.

  1. In iTunes select the “Edit” menu at the top of the screen, select preferences, go to the Advanced tab, make sure that “Share iTunes Library XML with other applications” is selected.

Setting up Plex

Go into Plex > Settings > Plugins and enable the iTunes Plugin.

OPTIONAL: Plex should be able to find the location of the iTunes library automatically, but if you show the advanced settings on this page in Plex, you will see a field in which you can specify the path to the iTunes Library XML file. Type in the path to the XML file without quotes and without the filename. As an example, if you have iTunes installed on D:\iTunes then D:\iTunes is the path to specify. You should see a file called “iTunes Library.xml” in this directory.

Restart Plex for this setting to take effect.

Note: I’ve noticed that when I look at this field later, after setting up Plex, Plex may automatically add the filename to the path. That’s okay.

You should now have a “…” menu to the right of “Playlists” in Plex. Selecting that menu will give you an option to import from iTunes.

Note: For the import option to work you should already have your music Library created in Plex. If you have no libraries created, then trying to import playlists will result in an error.

When you first create the library in Plex, on the Advanced tab of the “Add Library” screen, make sure to select the “Import from iTunes” checkbox. If you already created the library without importing, simply click on the “…” to the right of “Playlists” and then select “Import from iTunes…”

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