How do I put a folder of songs in its own playlist?

I battled with iTunes for a really long time because I am ahuge music lover and desperately wanted to be able to efficiently move some of my music collection over to my iPhone. Though I had some limited success, it was always a super pain in the butt and left me feeling like I had wasted a bunch of my day every time I went through the cumbersome task.
I realize some folks are able to navigate iTunes with Jaws, and maybe I just haven't put enough effort into it, but I have spent many hours trying many different suggestions, reading online tips, listening to Moslin's podcast about it and on and on, and yet iTunes remains a frustrating mess on windows.
I finally just gave up and purchased a spotify subscription, where I can find most of the music I want, though it is a less than ideal solution.
Why iTunes has to be so difficult with the most popular screenreader out there, I do not know, but I lay a good bit of the blame on Freedom Scientific. Given the popularity of iTunes, they should have long ago come up with a solution in the way of scripts to deal with this nightmare of accessibility.
I wish you much luck, and I know there are folks on the site here that are able to use iTunes, I just wish I knew the spell they are casting, cause it seems like magic to me.
, fare thee well, and please let us know if you get it figured out.

The one thing that helped me to get along with iTunes was to embrace it fully. I have many decades of computer experience, and it was tough to let go of manual file and folder management. I still struggle to call them folders, rather than sub directories. Anyways, a couple thoughts on your issues.

I know you have carefully curated your playlist folders. You could work with them intact, and still successfully use iTunes. However, what saved my sanity was to let go of worrying about them. I have an idea of how you might get iTunes set up as you wish, but it would be for a one time set up. It would not be a great way to continue to be able to maintain playlists through direct folder management.

Since you don't have the songs in iTunes at the moment, you could import each folder, one at a time, and once the folder is imported, select the songs from that folder and add them to their own playlist.

You can have iTunes sort its main listing by Date Imported. This would give you the list in chronological order and make it easy to figure out what was imported in each batch.

You can leave your folders intact, and set up iTunes in the Preference to not manage files and folders. It will import the files, but not change their location. However, if you make manual additions, subtractions, or movements of files, iTunes will not know what you did and the internal links to the files will be broken.

My suggestion is once everything is imported, let iTunes manage your files.

You can then add songs directly in iTunes, and also manage any changes to your desired playlists in iTunes.

Jessica, you can do this. I've seen your posts over time, and I know you are smart capable, and curious. I'll lay out what i can, but in the end you will need to do a little digging.

I cannot help you with keystrokes on your Mac. I think you said somewhere you were running iTunes in a virtual Windows machine. Given how much better the OSX version of iTunes is said to be, I'd switch to that if you haven't already.

Creating the new, empty playlists is straightforward menu stuff. I know you can make that happen.

Copying music files from external folders is as simple as selecting the files, using a copy command like Windows' CTRL-C, and then pasting them with CTRL-v. Rather than pasting into the iTunes program window, I suggest sniffing around and finding an iTunes generated folder called, "Automatically Add to iTunes." It's an easier way to go once you find that folder. I have a shortcut to it on my desktop.

Sorting the iTunes listing by different fields has always been tricky for me. I have had success using the JAWS virtual cursor to find the column headings. I have to admit I have asked for sighted assistance when I just didn't want to fight with it. I have no idea how much access you have to the column headers on your Mac. I would hope more than I do..
Once you have a playlist folder imported into iTunes, by copying it from your source folder, and then pasting it in the Automatically Added to iTunes, the tracks will show up in the main iTunes library.

The first folder will be easy to put in a playlist. Just select all files, and use the menu option to add files to your selected playlist.

When you import your next playlist, and if you sort by Date Added, you will have the new files on top of your library list. Well, assuming you have it from newest to oldest. They could be at the bottom if you have it oldest to newest.

Then In Windows, I would select the first file, and do a CTRL SHIFT HOME to select all the items for the next playlist and then add them to their iTunes playlist. using the Utilities or Context key, or even the File menu.
Repeat as necessary to import each of your folders.

I have no experience with OS X and its version of Voice Over. I expect my action steps would work for you, but I can't help you with the specific keystrokes needed to work that out.

Perhaps someone can help "translate" for us.

Hi Jessica,

I, too, had struggled with this issue for years, as I manually managed music on my hard drive; only getting my iPhone made me surrender control to iTunes. I have solved the problem of putting music in folders into iTunes playlists. This assumes that the songs are not already in iTunes. I would also recommend you make sure your files have appropriate meta data tags, as you will end up with a big mess in your library if they don't. (There are scripts to fix this, but from your posts it doesn't seem like you're ready for those.) Anyway, here goes:

1. Locate the folder with the music files you want to group in Finder. Do not open this folder.

2. Issue the "Mark item for drag and drop command". I think it's VO comma, but I've since reassigned all my drag and drop commands because I knew I wouldn't remember those combinations. Let me know if you would be interested in doing this. If VoiceOver tells you that the item is not drag-able, listen to it and interact with the list view table.

3. Open iTunes, and select the Playlists radio button. Interact with the table of playlists and make sure you are at the top.

4. Issue the "drop Item on VoiceOver cursor" command, VO period. Please note that if you are on a specific playlist or issue a "drop item before/after vO Cursor" command, iTunes will add the songs to the currently selected playlist. So if you want to make a brand-new playlist, make sure you are at the top of the tree. You will now hear a series of swooshing sounds as voiceOver tries to drag your folder. If you get a "failed to insert" message, try again or make sure both windows are visible on the screen by bringing your Finder to the front.

5. iTunes will now put you in a very helpful edit field with the name of the folder already inserted. Click OK or type another name.

6. You can now continue adding songs to this playlist. If you are done with it, click the Done button.

I hope this helps. It took me a while to solve this problem, but I'm very glad I did and very glad that Drag n drop helped me accomplish this.

You seem to not know all the VoiceOver keystrokes; Apple has tried to help. Issue a VO H, H command (that's two h's quickly) and you will be placed in the Commands help menu. Then start typing what you think you want VoiceOver to do; the list will narrow as you type. This is how I looked up the obscure defaults for Drag n Drop. Just thought I'd let you know.

Chelsea

I struggled for a long time with iTunes. Eventually got everything set up almost as desired yet it is tedious. When my audio collection got too big for the internal drive I had to move it all to another drive. iTunes needed to be tediously relinked to the new drive. Screw that time wasting chore. I discovered KODI. KODI is well designed and free open source media manager with an Android and iOS app to remotely control your media playback. Genious solution. Don't waste your time anymore with iTunes. Eventually an iTunes update will screw everything up or eliminate previous functions. KODI will let you keep all your music in folders and subfolders and should you decide to move things around it won't go bonkers.