When To Clear the Cache?

I’ve started trying Autoptimize with a couple of sites running WP Super Cache that are managed via MainWP, and I’m wondering when–or if–I need to clear the Autoptimize cache. The FAQ doesn’t seem to go into this, though it does mention that with some caching plugins there is an interaction between Autoptimize and the caching plugin.

1. If I update a plugin with updated CSS and/or JS files via the WordPress Admin Updates page, do I need to clear the Autoptimize cache and WP Super Cache, which most likely will refer to Autoptimize files that contain the plugin’s out-of-date code?
2. If I’m updating plugins via MainWP, or some other external WordPress management UI, do I need to clear the Autoptimize cache and WP Super Cache?