diff --git a/security/Makefile b/security/Makefile
index a498d8f697d7..afb4b76c795f 100644
--- a/security/Makefile
+++ b/security/Makefile
@@ -186,7 +186,6 @@
     SUBDIR += ruby-mcrypt
     SUBDIR += ruby-openssl
     SUBDIR += ruby-pam
-    SUBDIR += ruby-ssl
     SUBDIR += ruby-tcpwrap
     SUBDIR += saferpay
     SUBDIR += saint
diff --git a/security/ruby-ssl/Makefile b/security/ruby-ssl/Makefile
deleted file mode 100644
index e89b417ade67..000000000000
--- a/security/ruby-ssl/Makefile
+++ /dev/null
@@ -1,51 +0,0 @@
-# New ports collection makefile for:	Ruby-ssl
-# Date created:		9 Jan 2001
-# Whom:			Akinori MUSHA aka knu <knu@idaemons.org>
-#
-# $FreeBSD$
-#
-
-PORTNAME=	ssl
-PORTVERSION=	0.3.3
-CATEGORIES=	security ruby
-MASTER_SITES=	http://www.notwork.org/~gotoyuzo/ruby/src/
-PKGNAMEPREFIX=	${RUBY_PKGNAMEPREFIX}
-DIST_SUBDIR=	ruby
-
-MAINTAINER=	knu@FreeBSD.org
-
-USE_OPENSSL=	yes
-USE_RUBY=	yes
-.if !defined(NOPORTDOCS)
-USE_RUBY_RD=	yes
-.endif
-USE_RUBY_EXTCONF=	yes
-
-CONFIGURE_ARGS=	--with-openssl-include="${OPENSSLBASE}/include/openssl" \
-		--with-openssl-lib="${OPENSSLBASE}/lib"
-INSTALL_TARGET=	site-install
-
-DOCS_EN=	ChangeLog doc/ssl.html doc/ssl.rd
-DOCS_JA=	doc/ssl.ja.html doc/ssl.ja.rd
-
-post-build:
-.if !defined(NOPORTDOCS)
-	cd ${WRKSRC}; \
-	${RUBY_RD} doc/ssl.rd > doc/ssl.html; \
-	${RUBY_RD} doc/ssl.ja.rd > doc/ssl.ja.html
-.endif
-
-post-install:
-.if !defined(NOPORTDOCS)
-	${MKDIR} ${RUBY_EXAMPLESDIR}/${PORTNAME}
-	${INSTALL_DATA} ${WRKSRC}/sample/* ${RUBY_EXAMPLESDIR}/${PORTNAME}/
-	${MKDIR} ${RUBY_DOCDIR}/${PORTNAME}/ja
-.for f in ${DOCS_EN}
-	${INSTALL_DATA} ${WRKSRC}/${f} ${RUBY_DOCDIR}/${PORTNAME}/
-.endfor
-.for f in ${DOCS_JA}
-	${INSTALL_DATA} ${WRKSRC}/${f} ${RUBY_DOCDIR}/${PORTNAME}/ja/
-.endfor
-.endif
-
-.include <bsd.port.mk>
diff --git a/security/ruby-ssl/distinfo b/security/ruby-ssl/distinfo
deleted file mode 100644
index f054d581f4ee..000000000000
--- a/security/ruby-ssl/distinfo
+++ /dev/null
@@ -1 +0,0 @@
-MD5 (ruby/ssl-0.3.3.tar.gz) = 3d980ade0497bcde7014b029db9679ff
diff --git a/security/ruby-ssl/pkg-comment b/security/ruby-ssl/pkg-comment
deleted file mode 100644
index 432efd60c856..000000000000
--- a/security/ruby-ssl/pkg-comment
+++ /dev/null
@@ -1 +0,0 @@
-SSL socket module for Ruby
diff --git a/security/ruby-ssl/pkg-descr b/security/ruby-ssl/pkg-descr
deleted file mode 100644
index 9d5315c3e3d5..000000000000
--- a/security/ruby-ssl/pkg-descr
+++ /dev/null
@@ -1,3 +0,0 @@
-This is a Ruby module for handling SSL sockets, ported from Python.
-
-Author:	GOTOU YUUZOU <gotoyuzo@notwork.org>
diff --git a/security/ruby-ssl/pkg-plist b/security/ruby-ssl/pkg-plist
deleted file mode 100644
index e968b35ce50f..000000000000
--- a/security/ruby-ssl/pkg-plist
+++ /dev/null
@@ -1,24 +0,0 @@
-%%RUBY_SITEARCHLIBDIR%%/ssl.so
-%%RUBY_SITELIBDIR%%/buffering.rb
-%%RUBY_SITELIBDIR%%/ssl.rb
-%%RUBY_SITELIBDIR%%/net/https.rb
-%%RUBY_SITELIBDIR%%/net/protocols.rb
-%%RUBY_SITELIBDIR%%/net/telnets.rb
-@dirrm %%RUBY_SITELIBDIR%%/net
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/cli.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/login.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/sample.crt
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/sample.key
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/svr.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/verify_cb.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/wget.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/wget2.rb
-%%PORTDOCS%%%%RUBY_EXAMPLESDIR%%/ssl/x509.rb
-%%PORTDOCS%%@dirrm %%RUBY_EXAMPLESDIR%%/ssl
-%%PORTDOCS%%%%RUBY_DOCDIR%%/ssl/ChangeLog
-%%PORTDOCS%%%%RUBY_DOCDIR%%/ssl/ssl.html
-%%PORTDOCS%%%%RUBY_DOCDIR%%/ssl/ssl.rd
-%%PORTDOCS%%%%RUBY_DOCDIR%%/ssl/ja/ssl.ja.html
-%%PORTDOCS%%%%RUBY_DOCDIR%%/ssl/ja/ssl.ja.rd
-%%PORTDOCS%%@dirrm %%RUBY_DOCDIR%%/ssl/ja
-%%PORTDOCS%%@dirrm %%RUBY_DOCDIR%%/ssl