Hi! tl;dr: fixed upstream, quick patch for 5.9/6.0 below.
SSL support in lighttpd of OpenBSD 5.9 (1.3.36) and OpenBSD 6.0 (1.3.38) is broken. Note: already fixed by upsteam in 1.4.40: https://redmine.lighttpd.net/issues/2729 Details and (upstream) patch: https://redmine.lighttpd.net/projects/lighttpd/repository/revisions/1ca52fdce3b87f7748dd5db6f59d738ed7a9efe1/diff/src/network.c When running lighttpd of OpenBSD 6.0, the error message is: (network.c.773) SSL: error:00000000:lib(0):func(0):reason(0) The following (crude) patch simply removes the check for SSLv2 and SSLv3 (it's vs. OpenBSD 6.0 lighttpd-1.4.38p1.tgz): --- src/network.c.orig Fri Dec 4 22:13:47 2015 +++ src/network.c Sat Sep 10 16:00:32 2016 @@ -766,7 +766,7 @@ SSL_CTX_set_options(s->ssl_ctx, ssloptions); SSL_CTX_set_info_callback(s->ssl_ctx, ssl_info_callback); - +#if 0 if (!s->ssl_use_sslv2) { /* disable SSLv2 */ if (!(SSL_OP_NO_SSLv2 & SSL_CTX_set_options(s->ssl_ctx, SSL_OP_NO_SSLv2))) { @@ -784,7 +784,7 @@ return -1; } } - +#endif if (!buffer_string_is_empty(s->ssl_cipher_list)) { /* Disable support for low encryption ciphers */ if (SSL_CTX_set_cipher_list(s->ssl_ctx, s->ssl_cipher_list->ptr) != 1) { BR, Walter PS: quick howto: The following works for OpenBSD 6.0 (tested i386), see https://www.openbsd.org/faq/faq15.html#PortsInstall for more information on building from ports. save patch as: /usr/ports/www/lighttpd/patches/patch-src_network_c cd /usr/ports/www/lighttpd make make install make clean /etc/rc.d/lighttpd start