Music content expires frequently

After a year of owning my Sq 2 Music watch, suddenly I frequently (every few weeks) get the notification "Content expired, Update your downloads to continue offline use". This is frustrating me, as it only shows up when I am about to head out for a run, and want to start up my music. It completely prevents me from playing any music.

Also, the updating process is not very clear or fast. I have to dig into my settings in the Garmin Connect app before I find the update setting hidden somewhere. It also requires a wifi connection on my watch, which I had to set up first when I was on vacation and not on my home network. 

All with all, lots of very frustrating steps that prevents me from easily listening to music during my workouts, which was my main reason for getting this wat je in the first place.

How can this be solved?

Cheers.