Hi Matias,
Could you check the Trimble Connect Sync log file?
It can be found by opening "Contact Support" from button with question mark.
There is link to a file in the bottom of the opening dialog.
Inside the file (a zip file) you should see folder with your own email.
You should find the log file under Logs folder.
If there is something that looks relevant, you can then actually use the contact support dialog and send the data to us.
Best regards,
Marko Myllymaa