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I'm attempting to copy song from iTunes to my iPhone. All versions of software are current. Trying to drag-and-drop from iTunes into my iPhone. This was simple at some point in Apple history. Now, nothing happens. The "traveling" icon (drag/drop) tells me there is 1 file being transfered, but no transfer ever takes place. An hour chatting with Apple Support with all their versions of "are you sure it's plugged in" from their troubleshooting clones got me nowhere.

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    Welcome to Ask Different :) How about adding the song to your iTunes library and syncing to your connected iPhone? – Nimesh Neema Mar 29 at 13:11
  • Can you add some more details (including screenshots) to explain how you are trying to get a track onto your phone? – nohillside Mar 29 at 14:16
  • The correct procedure for adding a song to your iPhone from a Mac or PC is to add the song to iTunes and then sync your phone. Unless you have changed some options (like sync only checked songs, and others) all songs in iTunes will be automatically copied to your Mac. So you don't drag and drop from iTunes to your iPhone. You drag and drop from your Mac or PC into iTunes and then sync your phone. – Steve Chambers Mar 29 at 19:26
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I had the same problem, trying to use drag-and-drop (as I'd always done) to add a media file (audiobook) to the iPhone.

When dragged to the iPhone, the item appeared in a small gray box with a red/white number such as "58." No idea what the number meant. In any case, I now know that the small gray box with the number is a visual cue that the dragged item will not be transferred to the phone.

After setting preferences to manual synch, this worked for me on a PC:

  1. Connect the device to iTunes.
  2. Select the device at the top of the screen (not in the sidebar). The iTunes Library view is replaced with your iphone view for "Settings" and "On My Device."
  3. In Settings>Summary, scroll to Options and check-in (or out) Sync your synching method.
  4. In Settings>Audibooks, check-in "Selected audiobooks." No need to actually select books from the list.
  5. Switch back to regular iTunes Library (at the top of the screen, click the " < " (back arrow).
  6. From the Library, select the media type and show it in grid view.
  7. Select the grid item (tile?) for the media file you want to transfer.
  8. Drag the item to the iphone. If drag-and-drop is working, then the entire iPhone and expanded content will be enclosed in a blue box.

Notes

  • After completing all of the steps, on the iphone, I had to leave "Synch" (see step 4, above) checked in. If I unchecked it, then all selected types of media were deleted from the iphone.
  • My environment: iPhone 10; Windows 10; software for both is up-to-date.

Apple updates its applications' behaviors more frequently than I transfer files. Consequently, figuring out what's changed and writing the steps for yourself seems to never be sufficient.

Having said that, I hope this helps at least a few people in the short term.

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