https://bugs.winehq.org/show_bug.cgi?id=57063
--- Comment #6 from asicosilomu@protonmail.com --- I am reporting again and it seems that something is definitely not working as intended. I regenerated both certificates with an expiry of 2029, in case the date was an issue.
Everything works fine under Linux, as always. I tried accessing the server using two browsers in Wine (Wine Internet Explorer and QtWeb) and they are experiencing similar difficulties. When tasked with the http url, both browsers load it fine.
When asked to go to https://rfdext.net or https://localhost, both browsers hang. IE appears to be doing nothing while QtWeb is stuck with a spinning loading indicator. No relevant messages in the terminal.
If I don't have the CA in system trust, they recognize that (disproving the original bug) and (sometimes) prompt a security warning. If I continue anyway, they both get stuck like before. I tried a clean wineprefix, using the openssl s_server, nothing would get these browsers to connect to my server over HTTPS.
These browsers probably use Win32 native APIs, which seem to be the point of failure. Installing Firefox for Windows (terrible idea, I know) in a clean wineprefix and navigating to https://rfdext.net works perfectly. Except, Firefox doesn't see my CA in system trust and gives me a security warning (possibly it doesn't use system trust by default?).
Maybe Wine's APIs are choking on my webserver cert for some reason? Or I'm missing something.