Thanks for the analysis that the problem is caused by a change in the SSLEAY_DIR/OPENSSL_DIR constant with OpenSSL 1.1. I've adapted IO::Socket::SSL in 2.040 (just released) to try both constants so the problem should hopefully be solved by simply upgrading to 2.040.

Apart from that the problem would have probably be found by the live tests (t/external) since these check if the default trust path can be used to verify the certificte of some common sites. Unfortunately Debian explicitly does not run these live tests by default. But it might make sense to run these at least once before shipping a new version.

Regards,
Steffen, maintainer IO::Socket::SSL

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