Q: Unable to drag songs from iTunes Library to my connected iPad.

Hi robert06,

Welcome to the Support Communities!

The articles below may be able to help you with this issue.

Click on the link below to see more details and screenshots. 

I've quoted some helpful highlights for you:

TURN OFF ITUNES MATCH ON COMPUTER

iTunes Store: Subscribing to iTunes Match

iTunes Match will automatically renew your subscription at the end of your 1 year subscription by default. To turn off Auto-Renew:

1. Open the latest version of iTunes.
2. Choose Store > Sign In.
3. Enter your Apple ID and password, and click Sign In.
4. Choose Store > View My Account. You may be asked to re-enter your Apple ID password.
5. In the "iTunes in the Cloud" section, click Turn Off Auto-Renew to the right of iTunes Match.

TURN OFF ITUNES MATCH ON IOS DEVICE

iTunes: How to add a computer or iOS device to iTunes Match

When enabling iTunes Match on your iOS device, the music library on your iOS device will be deleted and then replaced with your music in iCloud.   If you no longer wish to do this, turn iTunes Match OFF on your iPad.

 

1. On your iOS device, go to Settings > Music.
2. Tap the iTunes Match switch to OFF.

SETUP MANUAL SYNCING ON COMPUTER

Managing content manually on iPhone, iPad, and iPod

You can also manually manage music and videos on your device. Manually managing your device allows you to choose just the songs and videos that you want to have with you. This is especially useful if your iTunes library contains more items than can fit on your device. To add items to your device, simply choose a song, video, or playlist from your iTunes library, then drag it to the iPhone, iPad, or iPod icon (under Devices) on the left-hand side of the iTunes window.

Configure iPhone, iPad, or iPod for manual management

To manually manage the content, follow these instructions:

1. Connect the device to your computer.
2. Open iTunes.
3. Select your iPhone, iPad, or iPod. If your device is not visible in the upper right corner of the screen, choose Library first.
4. Click the Summary tab and select "Manually manage music and videos".
5. Click Apply.
   

Manually add or remove content on your iPhone, iPad, or iPod

After following the steps above, you can add individual songs, videos, and playlists from iTunes to your device. To add content to your device:

1. Select your device.
2. Click "On this Device".
3. Then choose "Add to" in the upper right corner.
   While viewing the media in your iTunes Library, if you drag a song, video, TV show, or Movie a sidebar will show up on the right. You can drag content onto the device.  You can also create and modify playlists directly on the device.

Notes:

• You must first import audio CDs into iTunes before you can add them to your device. Get assistance if you're having difficulty syncing songs to your device.
• Even when manually managing music, some content may be available from only one library at time. This includes all content on iPhone and video content on iPod and iPad.
• Even when you have enabled manual management, you can still sync some content automatically. Select any content tab, such as Video, to enable automatic syncing for that type of content.

I hope this information helps ....

Have a great day!

- Judy

Hi Robert06,

I'm happy you are back on track!

Have a super day!

- Judy