Dropping person while their connection sleeping in SQL Server
When I try to drop a person that recently had a connection with SQL Server


Why are you doing this?  What drove the need to have to do this?

It sounds like you're running into connection pooling.  But connection pooling is there to help you, it's a great optimization.  By clearing the pool you're wiping out this caching mechanism.

My recommendation, without knowing more about what you are trying to do or what you need, would be to leave it as it is and let connection pooling do what it does best.