Chrome itself always requests HTTP first, except for HSTS and their own pinned certificates list which is actually shipped within the source code.

That's also a major difference to Ungoogled Chromium, where UC will request "https://..." by default if you just enter the domain.

So in the case of Enterprise Proxies that have no locally force-installed cert to sniff on internet traffic will likely end up with HTTP-everywhere being used. But usually employers that encourage such bad practices also install their snakeoil MITM certificates locally.