The Trust button under the SSL tab is unrelated to the error that you provided in the beginning of this topic. Clicking on the Trust button is meant to remove the self-signed certificate warning that you see when using HTTPS in your browsers.
We’re looking into why the “Trust” button will not go to “Trusted” on Windows after re-opening the SSL tab.
As far as the main issue goes, please see Unable to update WP Core and Plugins: cURL errors