I've found the same issue on Linux when using OpenSSL with TLS 1.2.
I've opened a Github issue for it: https://github.com/curl/curl/issues/7222


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________________________________
From: curl-library <curl-library-boun...@cool.haxx.se> on behalf of Daniel 
Jeliński via curl-library <curl-library@cool.haxx.se>
Sent: Tuesday, June 8, 2021 15:19
To: libcurl development <curl-library@cool.haxx.se>
Cc: Daniel Jeliński <djelins...@gmail.com>
Subject: Re: TLS session ID re-use broken in 7.77.0

Simple repro:
>curl -vI  --http1.1 https://example.com/[1-3] -H"Connection:close"

output of the old CURL version contains "* SSL re-using session ID";
output of 7.77.0 does not. Wireshark confirms that the old version
sent PSK in client hello, the new version did not.

curl 7.77 downloaded here:
https://curl.se/windows/dl-7.77.0_2/curl-7.77.0_2-win64-mingw.zip

Regards,
Daniel
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