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To add games there, just open them up to have them show as recent, then right click and select the "pin" option.
However, if you have too many non-games entries in there (which you can control via Settings - Interface - Taskbar Preferences), there might not be enough space for games. On win7 and 8 you could increase the jump list size via Start Menu customization, but for win10 i hear you need to edit the Registry.
Furthermore, the recent update of the Steam Client seems to have added a stupid restriction such that regardless of my Jump List size of 25 it will still only record 5 games in its list... so now my list is so much shorter than what i have become used to. :(
I'd forgotten about this thread. XD I contacted Steam support, it's actually a known issue I guess, but no ETA on a fix. Ah well. :)
The odd thing is that the two jump lists i can access right now have different contents, and different lengths too. Maybe they're tied to a specific version of the Steam client, and any update would de-sync them? ;-??
Huh, indeed, when i right-click on the start menu entry and go to properties, it shows it's a shortcut at AppData\Roaming\Microsoft\Windows\Start Menu\Programs, while the taskbar one is directly for the Steam.exe from Program Files (x86)\Steam... Maybe try to manually create a second shortcut in that Roaming\Microsoft\Windows\Start Menu\Programs folder, and see if THAT gets a jump list? ;-)