“On the 29 February each Contract Year, Service Provider shall…”
This is a real life snippet of a contract put together by a “top” law firm.
Our Wall of Shame is bursting with examples like this.
Automation alone won’t help you - it works best when contracts are written nicely.
Your contract database needs to assume and account for the very worst. For when your contracts defy logic itself.
For that, you’re going to need to get a person involved.