I've been spending the last days to find a way to have Garmin Express recognize my iTunes library and music and sync it to my Forerunner 965. I have an Intel Macbook Air running Catalina, so there is no formal "iTunes" anymore, but only the Music app. Using Garmin Express connecting the watch and clicking on "Music" the program ends up in an endless "loading" screen. No way to transfer any music. I've tried it on a friend's Windows/iTunes setup and it seemed to work, so there is clearly an issue with Mac and Garmin Express. Reading through various posts on different forums many users experience the same issue.
I've seen quite complicated workarounds and could come up with a possible solution, which I figured I share with you as it might be helful to some. I use a combination of a free mac software called iSyncer and Android File Transfer. It should work for older and newer macs (pre and post iTunes/Catalina). I've been using iSyncer for a long time to copy playlists from my library to SD cards to use in my car.
iSyncer allows you to copy your music/iTunes library playlist files into a different location, which is also the only drawback of my solution. You need to store the files somwhere.
For it to work correctly do this:
- Install iSyncer (no need for registration/payment - use the free version).
- Create a folder on any device in which iSyncer will safe the playlists/files. Ensure enough free space so your playlists fit.
- Open iSyncer and create a new profile. Your iTunes/Apple Music playlists should popup in the Music Playlist field. Select the one you'd like to transfer to the folder.
- As config use the Garmin folder structure: Playlist/Artist/Album/# - Song
- Add the new config so it appears below
- Save the profile
- In the main iSyncer window select profile and choose the dedicated folder as Destination folder.
- Hit the Sync button and wait until the desired files are all copied. You should now see the files with the desired folder structure in the destination folder.
- Install and start Android File Transfer
- Connect your Garmin watch
- There should be a "Music" folder visible
- Open the folder and drag&drop the files from the other folder
I have not experimented if other folder structures work or if you can add various playlists but I would guess so.
It's not perfect, but at least it keeps my music library intact, let's me create a dedicated playlist and easily sync it anytime I make changes. Also it overcomes a problem many have when having the library on an external drive. I have a huge library on my NAS and don't want to change that just because Garmin Express doesn't recognize anyhting else than the standard save location on the main drive.
The only drawback to me is, that I need to store the files somewhere for the transfer, unfortunately I don't know a way besides Android File Transfer to mount the watch folder structure. It does not show up in finder, so I cannot directly sync. Maybe one of you can think of a workaround there.