Have reviewed your install. This is due to the value of the "Propose plan for upgrades only if it is more expensive" parameter at time of expiration. If it was set to "No" when they expired it would've properly expired the previous and current subscriptions, but the other subscription is frozen in an upgraded from status since the user upgraded from it to another plan.
The only fix for existing expired subscriptions in this case is to modify the old subscription (its current status will be "Upgraded to other") in CBSubs > Subscriptions by clicking the # under the Id column and making the following changes.
Status: Expired
Previous Status: Upgraded to other
I've made this change to the test user provided where you can see it is now working fine. Now that your plans are set correctly however you should have no further issues for future subscriptions.