give it a skill that runs a timer in the background and every 4.5 minutes says "ping? pong!"
It would be interesting to graph the cost/savings of this approach based on context length, percent cached, etc.
The UI for this is a bit tricky, I could mark conversations as "active" and then do the ping/pong dance on only active conversations and up to some determined max cached (e.g. 1 hour).