How to jump the big iPhone hurdle—syncing to iTunes

My 160 gig iPod Classic just wasn’t pulling my music weight anymore. I was stuck in a cycle of needing to delete music every time I wanted to add more songs because I was totally maxed out. Meanwhile, my iPhone 5 battery was dying a quick death, and the screen was too small for my dying eyes.

I was finally ready to make the leap to an all-in-one pocket device. The 256 gig iPhone 7 Plus Red hit the market around my birthday, with some proceeds going to HIV/AIDs research. The investment seemed totally worth my husband’s hard earned money.

The transition wasn’t swift. I didn’t want to just dump my tired old playlists onto my shiny new phone. So I spent four obsessive months reorganizing – deleting songs, adding songs, updating playlists, creating fresh artwork for albums and playlist covers, re-ripping from CD any MP3 files in my iTunes with superior AAC versions (and it was about a 50/50 split in my pod of nearly 20,000 songs).

Finally, it was time to make the connection and transfer my whopping library to my phone.

It was a disaster. And I soon learned it is for pretty much everyone who uses Apple products these days and dares not sign up for one of their streaming cloud services but chooses to sync their own music from their computer to their phone.

About 1/4 of my songs transferred before iTunes crashed, attempting for hours to continue, seemingly erasing everything it had already succeeded in transferring several times and starting over, spinning in circle at times, locking up completely with no progress at others. When I finally gave up and forced an ejection, My phone was a mess of songs, some with art, some without, some grayed out and unplayable.

And so began my agonizing Internet research through a half decade of message boards and help pages to try to fix the problem. Yes, this has been an issue Apple hasn’t addressed or corrected for at least that long. Very often, the advice was one of the following: subscribe to Apple Music; subscribe to iTunes Match; buy this completely different program that syncs your music to your phone with no issues at all!

Suck my dumpy dick, Apple…and you other companies with your faux troubleshooting pages that are really just long-assed ads for your own music software. I’ll figure this shit out myself.

After several more excruciating nights of trial and error using various suggestions I’d found online, well, I lost all my playlists from iTunes.

Suck my dumpy dick hard, Apple.

That’s right. Although the sync goes from computer to phone, somehow, my phone at one point wiped away all the playlists on my iTunes when I connected it. And guess what? The tried and true technique for reimporting the file from the iTunes program folder on your computer that holds the information with your playlists on it DID NOT WORK. Which means that file was somehow wiped clean. Which means I had to then take the time to rebuild every playlist before continuing with troubleshooting how the fuck I was going to make my phone my pocket jukebox.

When I was done picking up the pieces of my life, it was back to getting the music onto my phone. Here were the specs of my PC and device when I first began syncing them:

PC with Windows 7 running iTunes 12.6.2.2

iPhone 7 Plus Red with IOS 10.3.3

Hopefully, if you’re in the same boat I was in, the steps I lay out below will help you, too. Just note that I have only music in my iTunes and I have only AAC files I’ve ripped from my own CDs or dropped into iTunes after a download. I’ve never purchased a file from iTunes, so I have no concerns about my phone refusing to sync due to licensing and sharing issues that force you to subscribe to Apple Music in order to listen to your own purchased music.

Rather than the insane solution offered on many sites of completely wiping your phone clean and starting all over again because your first try at syncing didn’t work, I simply wiped all the MUSIC off my phone – the random tracks and grayed out tracks that were already on there from my previous attempts at syncing. To do so, I went to Settings > General > Storage & iCloud Usage > Manage Storage (under STORAGE, not the iCloud storage section below that) > Music. There you will see “All Songs.” Swipe that sucker left, hit delete and it’s all gone. Kind of…

I was still stuck with all those grayed out – or “ghosted” – songs. Unplayable, but didn’t delete. You can trash them individually by clicking on them in the Music app on your phone, but if like me you have loads of them, it would cause carpal tunnel. So…I connected my phone to my iTunes. But first, I did some things I’d learned during my research.

For starters, I set my iTunes NOT to auto sync. In iTunes, go to Edit > Preferences.

Choose the Devices tab, then click the box that says “Prevent iPods, iPhones, and iPads from syncing automatically” and hit OK.

Next, I set my PHONE to Airplane Mode. Various sites insist that this is important for ensuring phones sync with iTunes. While I applied several troubleshooting solutions at once, I kind of buy it, because Airplane Mode prevents your phone from receiving calls or texts, and I wouldn’t be surprised if those types of interruptions are what were interfering with the transmission of my sync efforts the first time and causing the continual retries.

After that, I connected the lightning cable to my iPhone 7 Plus Red (gotta add the Red) then plugged the USB into my computer. The phone shows up in iTunes but does nothing. Yay! That’s exactly what I wanted.

Up on top of iTunes on the left, you’ll see a little phone icon.

If you click on it, you’ll get a left sidebar menu for your iPhone just like you do for your iTunes music. The main screen will switch to the “Summary” screen.

Down at the bottom, under Options, check “Sync only checked songs and videos” AND “Manually manage music and videos.” If you don’t check this second one, you won’t be able to delete those pesky gray ghosted songs. Hit Apply at the bottom.

Now hit the back arrow at the top of iTunes. In the left menu, under Devices, click on your phone (whatever name you’ve given it should be there) and it will have a default list of menus (Music, Movies, TV Shows, Books, etc.).

Click on Music and all your grayed out songs will show up. Select them all (Ctrl A on PC) then right click your mouse, and you will see a choice to Delete from Library just as you do when you delete songs from iTunes. Wahoo!

Do the deed. The computer will go through the syncing process of deleting all the tracks from your phone so your Music app will be completely free of any song or artists.

When none appear under Music on iTunes (I ejected the phone and totally checked under the app to make sure they weren’t showing once the phone was running independently of the computer), arrow back again until you can click on the phone icon again to return to the Summary window. While in the Summary window, click on Music in the menu to the left below Summary. At the top of the new window that appears, check the “Sync Music” box. Under that, check the circle that says “Selected playlists, artists, authors, and genres.” This turns off the “Entire music library” button above it. I also unchecked anything below that since I’m strictly about the music.

A list of your playlists will appear below that window on the left, and to the right a list of artists. You can select just artists if you want, or just playlists (it will transfer only songs that appear in those playlists, so if you want all the songs by a particular artist even if they’re not in your selected playlists, you must select the artist as well).

Once you’ve checked all your choices, hit apply at the bottom, and the progress bar will begin going through the various steps of syncing those artists and playlists to your iPhone.

Now here are the problems I faced when I first tried this method and how I ironed out the wrinkles:

  • Most important, if you add playlists bit by bit like I did, know that when you go back to the “Sync Music” screen to add more playlists, although your instinct might be to uncheck the already checked playlists since you already did them, DO NOT UNCHECK THEM. I learned the hard way that unchecking them tells iTunes to DELETE them from your iPhone. Motherfucker. In other words, once you’ve added playlists to your iPhone, even if you haven’t updated them since the last time you synced, they must forever stay checked on this page because iTunes is not just syncing what you check off, it’s taking this as a checklist of everything you want on your iPhone. Think of it this way: when you automatically sync upon connecting iTunes, it just scans for new music and adds it where needed while leaving everything else alone, and if you’ve removed anything since the last update, it takes that off your device. This is the same idea.
  • If when you return to the “Sync Music” page the box needs to be checked again next time you want to update, you will get a warning about it wiping out everything on your device and replacing it with everything in this library. Don’t worry. As long as you see that the “Selected playlists, artists, albums, and genres” button is checked, when you confirm, you will get the usual playlist and song check boxes and be able to choose what to update on your iPhone.
  • Artwork issues. The first time I synced my playlists manually, I added four short ones. I watched as the songs were transferred very quickly. And then…I watched as I got the same old spinning and freezing for over 3 hours while iTunes tried to add the artwork. Actually, I didn’t watch. I went to bed, woke up 3-1/2 hours later and found it in the same state, went back to bed, and woke up 4 hours later to find that at some point, it had succeeded! Now, I don’t know what went wrong and why it took so long, but my next time with one single short playlist took only minutes, including artwork. But here are some things I noticed about my first attempt. When I checked to make sure everything had transferred to my iPhone, I did discover that one song in one playlist did not have the new artwork I had made. Apparently I missed updating that song, and it still had the old artwork—artwork that was sized per specs for my iPod classic. The image was twice the size of the current specs for iPhones and also rectangular shaped, while current iTunes calls for square shapes (I’m using images that are 300 x 300). Perhaps that was the problem. Another issue, and it was only one, involved playlist cover art. For most of my playlists, I created different art for the cover of the playlist than the album art for the songs in it, and all the songs within the playlist use the same album art photo. However, for one particular playlist, I used the same artwork for cover and album art, but I also had a few songs in the playlist that had different album artwork. When this playlist transferred over to my phone, the image did not set as the cover art. Instead, I got that 4-quadrant solution iTunes applies using album art from songs in the playlist when no cover art is assigned, as in this example in iTunes, on my phone!On a hunch (Jinkees! I said “hunch”), I designed different cover art for the playlist, and when I next synced my phone, the cover art was properly placed on its own. So either using the same art for playlist cover and an album within the playlist confuses the system, or using different album art on songs within the playlist does. I’m not sure.
  • Still on artwork, a general rule I noticed…every time I would sync my phone with iTunes, after it was done and I ejected my phone, the cover art for each playlist had been removed from iTunes. WTF?

    Can you guess what the solution was when I researched this issue? Sync your phone with no music checked, then sync it again with the music synced. Now, I don’t know if that would work to resolve the problem since I didn’t try it. Why? Because do you realize what that “solution” actually does? It removes everything from your phone (when you sync with nothing checked) and then puts it all back on again (when you sync again with everything checked). REALLY? Do we really want to go back down that path of starting all over again now that I’ve managed to get 20,000 songs on my phone? My personal solution was to just remember to re-add the cover art to each playlist after every sync so that the next time I sync my phone it wouldn’t be removed from that as well. Grrr…argh. The good news is, after the next itunes software update, this issue went away, but if it were to return, I wouldn’t be surprised…

  • Another issue I’ve had is one–JUST one–playlist that occasionally DUPLICATES in both my itunes and on my phone when I sync. My 90s music playlist ends up appearing a second time with the addition of a number 1 at the end of the title every 3rd or 4th time I sync, so I have to MANUALLY delete the duplicated playlist from both my phone and itunes. I finally got sick of doing this, so as a test, I created a new folder, dragged all my 90s songs into it, and gave it a new 90s playlist name, then deleted the old 90s playlist and did a sync of my phone. So far, I have yet to suffer a duplication of the new, renamed playlist!

Once I got past those stumbling blocks, manual sync worked like a charm and I now prefer it to auto sync. Initially, I only transferred a few playlists at a time rather than attempt to transfer all 20,000 songs at once, and even selected single playlists to sync if they were particularly long (anything over 2000 songs). Hell, I even transferred my 80s playlist in small chunks (it includes over 10,000 of the 20,000 songs in my iTunes).

So there you go. I did it. I took a bite out of the big Apple, and now I have the all-in-one iPhonePod I was hoping for. But I’m not going to lie, while there are some perks, there are some functionality issues I sure miss from the old iPod, like the big one…the device staying exactly where you were in a playlist and on a song the last time you listened. With the Music app on the phone, if you pause your music and shut that app off completely so as to preserve battery, kiss that pause position goodbye! Better remember the last song you were playing so you can go hunt for it in your playlist to pick up where you left off the next time you listen to music. Let me tell you, that’s just loads of fun trying to do in an 80s playlist of over 10,000 songs that are uniquely sequenced, not simply alphabetical by song title or artist.

Is there a fix for this? Well, the solution for me is to NOT quit out of my Music app. At night, I power my phone down completely, so I just leave the app open when I do, and when I turn it back on, it’s still paused on my last song.

The other “solution” I found online is that you can change the options on every single song in your iTunes and every song you add going forward to enable “Remember playback position.” I’ll tell you how to do it, but wait until you hear the drawback before you apply it.

To enable “Remember playback position,” right click on a song, or select all songs then right click, and go down to “Get info.” In the window that appears, select the “Options” tab. Under playback you’ll see the “Remember playback position” checkbox. Click it to enable it. If you have selected all your songs, it will take a bit of time to apply to all the songs.

Does it work on remembering where you left off on your song on the phone? I’m not sure, because I never bothered to sync with the feature enabled. Here’s why. In iTunes, the feature causes the program to remember the place you left off on a song even if you leave that song and start playing another song. In other words, it isn’t just a bookmark for the last song you were listening to, it’s a bookmark that remembers where you left off playing every song for which it is enabled. So you may click on a song expecting to listen to it from the start, not realizing that the last time you listened to it you stopped somewhere in the middle of the song. Well…iTunes realizes it and starts it from that spot. Argh!

That’s it, Apple. Keep sucking, because I’m about to blow…

If you have any questions about what I covered, suggestions to help me out with some of the problem spots I still have (like that damn disappearing artwork issue),  or if you have any tips that I missed, let me know and I’ll incorporate the information into this post. Thanks!

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