Hey there @Arkamos,
Thanks for reaching out to us about this - we'll be glad to help you out here.
If the Recently Played section of your Spotify desktop app doesn't update properly you might have encountered an issue that was reported to us in the past and we're still collecting info from our users to look further into it.
Check out this Ongoing Issue and add your vote to it by clicking on the +VOTE button. Make sure you follow the steps under Status Update as well. It'll also be useful to Subscribe via the three-dots menu in the top right corner next to the title. This way you'll stay up to date with any relevant updates about this.
Hope this helps. Let us know if you have any questions.
