If you update the CALMP KEYS file and choose to NOT recycle any of the products, when each of the products reassesses the file the next time (within an hour), the product will recognize that the file has changed and reprocess all the keys to pick the "best one". And, you will see the results of reading/validating each key in the product's console. If any are invalid, expired, whatever..., that should be indicated for that particular key.
For each product/code as long as there is a valid and unexpired key in the CALMP KEYS file for that product/code, the product will not give violation messages when commands are issued. If there are multiple valid and unexpired keys for a product/code, then the "best" key is used ... that is, the one that has the longest expiration date into the future.
When keys are within 30 days of expiring you will get messages on the product console about "the key will expire in NN days", but commands will not get violation messages until the keys expire.
We recommend when you first see the "keys are expiring" messages on the console(s), obtain new keys and install them. After, you will see that the "keys are expiring" messages go away (within an hour) on each product console.