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Garmin Express fails to upload some Files to Garmin Connect

HI,

after years of flawless operation I encounter issues with syncing my Garmin Fenix 6X Sapphire. Garmin Express complains with the following message:

So, I followed the advice (link in the error message) and worked myself through the steps. After sync (and the associated error message) the folders in my OS X library of the corresponding device are empty (no leftovers that failed to sync):

Interesting enough, when I sync again, the error message as well as the filetree look different:

I installed Android File Transfer and tried to find the files shown above, but no luck.

Does anybody have a small hint what I could do to fix the error? Since the content of the error message keeps changing with every sync operation it seems very difficult to track down.

Many thanks in advance.