How do you make sure your contractors are still insured?

We recently had a customer who used outside contractors for cleaning. Their contractors were insured when they were awarded a biannual contract but the insurance ran out and had not been renewed by the cleaning contractors. This left our client with a liability claim against them after an accident. This led me to wonder just how everyone keeps track of making sure their contractors documents and insurance are up to date in their organisations? Most people use spreadsheets but here's no way to ensure that 500 suppliers across multiple documents are up to date without manually checking them this way.