I had to manually install libnet-ssleay-perl libcrypt-ssleay-perl libio-socket-ssl-perl to get TLS to work.
$ lsb_release -sdc Ubuntu 16.04.6 LTS xenial $ apt-cache depends sendemail sendemail Depends: perl Depends: libio-socket-inet6-perl Suggests: libio-socket-ssl-perl Suggests: libnet-ssleay-perl -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/237964 Title: missing dependences To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/sendemail/+bug/237964/+subscriptions -- ubuntu-bugs mailing list [email protected] https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs
