Any ideas?

Oddly, I get the same "Can't connect to www.cpan.org:443" error using Strawberry Perl 5.24.1 on Windows 11, whereas Strawberry Perl 5.24.4 (on the very same machine) retrieves the page just fine.
On SP-5.24.1:

D:\>perl -le "print $];"
5.024001

D:\>\b\pmver WWW::Mechanize
1.83

D:\>\b\pmver Crypt::SSLeay
0.72

D:\>\b\pmver Net::SSLeay
1.80

D:\>\b\pmver IO::Socket::SSL
2.043

D:\>\b\pmver Net::SSL
2.86

D:\>\b\pmver LWP::Protocol::https
6.06
[download]

On SP-5.24.4:

D:\>perl -le "print $];"
5.024004

D:\>\b\pmver WWW::Mechanize
1.88

D:\>\b\pmver Crypt::SSLeay
0.72

D:\>\b\pmver Net::SSLeay
1.85

D:\>\b\pmver IO::Socket::SSL
2.056

D:\>\b\pmver Net::SSL
2.86

D:\>\b\pmver LWP::Protocol::https
6.07
[download]

("pmver" is just a local batch file that prints out the version number of its argument.)

<UPDATE>:
They both use different versions of openssl, too. SP-5.24.1 has 1.0.2j and SP-5.24.4 has 1.0.2o
</UPDATE>

Is there anything in there that helps ?

Cheers,
Rob