Best way to do that is probably using CBSubs Promotions and a negative promotion, which will increase the price instead of decrease. Example as follows.

Basic
Promotion Type: Applies to all purchases
The promotion is: A: A fixed amount A
Fixed Discount Amount in currency above: -50
Advanced
Which plans must be purchased at same time: SELECT_PLAN_HERE
Conditions
First condition: This condition:
Any of the following plans subscriptions: SELECT_PLAN_HERE
Must be in state: Expired

That should increase the cost of the selected plan by $50 if they've an expired subscription to it. Grace period prevents a true expiration state so this will work with grace period as well.