See the upstream bug background https://github.com/openssl/openssl/issues/1418 The issue initially was caught in a case when developers works behind company firewall and requires install company self signed certificate on Ubuntu host in order to access internet via company proxy. User may experience unable to access internet services via https protocol when even manually installed root trust ca-certificate on host machine due to openssl unable to verify some type of self signed certificate. This is also causing problems for snapcraft developers who work behind proxy servers unable to build snap packages. There is a fix going into openssl upstream apparently https://github.com/openssl/openssl/pull/10587 Just create a bug here to track this issue in Ubuntu in order to make sure we merge upstream fixes ultimately. Similar case reported by other users: [1] https://serverfault.com/questions/966846/cannot-trust-development-https-self-signed-certificate-in-ubuntu-18-04-2-lts [2] https://stackoverflow.com/questions/55485511/how-to-run-dotnet-dev-certs-https-trust/59702094#59702094