Every time you write a check for a recurring service, in the memo field include "services through X", so you will always know that you were paying for services

Every time you write a check for a recurring service, in the memo field include "services through X", so you will always know that you were paying for services through a given date, and it won't matter if it's paid before or after the services are rendered. Similarly, every invoice you got from Met Life should also have a coverage date range on it. Shouldn't ever be ambiguous.