And that doesn’t explain why listening music on any of my desktop apps don’t affect the shortcut suggestions. Maybe that's because Recently Played music doesn't sync to the web player as well? So if web player doesn't see any listening history then it doesn't offer anything new in the shortcuts as well?
I did a video for you. Explanation to the video:
1. I start playing Your Time Capsule in my Mac's desktop app.
2. Then I open the web player where it shows Your Time Capsule in the Recently Played section
3. Then I switch back to the desktop app and close it
4. Then I switch back to the web player and refresh the page
5. And the Your Time Capsule is gone from the Recently Played section in the web player
Notice the other playlists in the Recently Played section. I listened to them in the web player and they synced to the desktop and mobile apps just fine.
So yeah, it seems to be that something is broken with history sync between platforms and that also affects the shortcut suggestions.
Thanks for reporting this to us.
First, we'd recommend trying a clean reinstall of the app on your device by following the steps here.
If after that you’re still having trouble with this, could you provide us with the following info:
device + OS version
exact Spotify version
do the shortcuts update when you use the web player
Once we have that, we will pass it on to the relevant team, who will look further into it.