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Re:Building a new Windows 3.1 app in 2019: A Slack Client by mkj on Thursday December 19, 2019 @01:26AM (#21832484)
Aaw cheating with https. I wonder if an embeddable library like BearSSL would be hard to get working.
Re:Building a new Windows 3.1 app in 2019: A Slack Client by yeokm1 on Thursday December 19, 2019 @03:45AM (#21833132)
Something I can try next time! I didn't know about BearSSL before
Re:Building a new Windows 3.1 app in 2019: A Slack Client by anthk on Friday December 20, 2019 @12:24AM (#21841906)
Or FreePascal/Lazarus with OpenSSL. If you build a Win16 statically linked binary it may work.

https://wiki.freepascal.org/Win16