diff --git a/devel/ruby-zentest/Makefile b/devel/ruby-zentest/Makefile
index 62003d65ab5..0d6b4259813 100644
--- a/devel/ruby-zentest/Makefile
+++ b/devel/ruby-zentest/Makefile
@@ -1,10 +1,9 @@
-# $OpenBSD: Makefile,v 1.14 2013/03/11 10:50:30 espie Exp $
+# $OpenBSD: Makefile,v 1.15 2013/07/03 06:56:01 jasper Exp $
 
 COMMENT =	ensures test coverage and accelerates TDD
 
-DISTNAME =	ZenTest-4.1.4
+DISTNAME =	ZenTest-4.9.2
 PKGNAME =	${DISTNAME:L}
-REVISION =	7
 CATEGORIES =	devel
 
 # MIT
diff --git a/devel/ruby-zentest/distinfo b/devel/ruby-zentest/distinfo
index 9e527ca180f..3e20209ab56 100644
--- a/devel/ruby-zentest/distinfo
+++ b/devel/ruby-zentest/distinfo
@@ -1,5 +1,2 @@
-MD5 (ZenTest-4.1.4.gem) = fgzQKHmP2EmAkKAQDhvEbQ==
-RMD160 (ZenTest-4.1.4.gem) = 6reYYjvYGeXthaVpP4fiTnw9qyk=
-SHA1 (ZenTest-4.1.4.gem) = 5knfTLSCpes+9rEJpX88J/RVWRI=
-SHA256 (ZenTest-4.1.4.gem) = mIT85GVotG7i0axhJIVYwCXV82sWKGwfpKHt/DEXIyo=
-SIZE (ZenTest-4.1.4.gem) = 60416
+SHA256 (ZenTest-4.9.2.gem) = 8dq0jVTzCdOCnxtvLzS7Ky61NYyqd8rf8PLTkW/fH6I=
+SIZE (ZenTest-4.9.2.gem) = 69120
diff --git a/devel/ruby-zentest/patches/patch-Rakefile b/devel/ruby-zentest/patches/patch-Rakefile
new file mode 100644
index 00000000000..5a8f45cada5
--- /dev/null
+++ b/devel/ruby-zentest/patches/patch-Rakefile
@@ -0,0 +1,16 @@
+$OpenBSD: patch-Rakefile,v 1.1 2013/07/03 06:56:01 jasper Exp $
+
+Revert https://github.com/seattlerb/zentest/commit/99c4a39041c3431eae3ad838b7e663933b2d0c2e
+which throws: Illformed requirement ["< 2.1, >= 1.8"]
+
+--- Rakefile.orig	Sun Jun 30 20:15:59 2013
++++ Rakefile	Sun Jun 30 20:16:21 2013
+@@ -13,7 +13,7 @@ Hoe.spec "ZenTest" do
+   developer 'Ryan Davis', 'ryand-ruby@zenspider.com'
+   developer 'Eric Hodel', 'drbrain@segment7.net'
+ 
+-  require_rubygems_version [">= 1.8", "< 2.1"]
++  require_rubygems_version "~> 1.8"
+ end
+ 
+ desc "run autotest on itself"
diff --git a/devel/ruby-zentest/patches/patch-_metadata b/devel/ruby-zentest/patches/patch-_metadata
new file mode 100644
index 00000000000..583cb14450c
--- /dev/null
+++ b/devel/ruby-zentest/patches/patch-_metadata
@@ -0,0 +1,21 @@
+$OpenBSD: patch-_metadata,v 1.1 2013/07/03 06:56:01 jasper Exp $
+
+Revert https://github.com/seattlerb/zentest/commit/99c4a39041c3431eae3ad838b7e663933b2d0c2e
+which throws: Illformed requirement ["< 2.1, >= 1.8"]
+
+--- .metadata.orig	Sun Jun 30 20:18:26 2013
++++ .metadata	Sun Jun 30 20:19:33 2013
+@@ -192,13 +192,6 @@ required_rubygems_version: !ruby/object:Gem::Requireme
+       - 1
+       - 8
+       version: "1.8"
+-  - - <
+-    - !ruby/object:Gem::Version 
+-      hash: 1
+-      segments: 
+-      - 2
+-      - 1
+-      version: "2.1"
+ requirements: []
+ 
+ rubyforge_project: zentest
diff --git a/devel/ruby-zentest/pkg/PLIST b/devel/ruby-zentest/pkg/PLIST
index 157181bf561..621aed217dc 100644
--- a/devel/ruby-zentest/pkg/PLIST
+++ b/devel/ruby-zentest/pkg/PLIST
@@ -1,4 +1,4 @@
-@comment $OpenBSD: PLIST,v 1.4 2010/11/08 23:24:41 jeremy Exp $
+@comment $OpenBSD: PLIST,v 1.5 2013/07/03 06:56:01 jasper Exp $
 ${GEM_BIN}/autotest${GEM_BIN_SUFFIX}
 ${GEM_BIN}/multigem${GEM_BIN_SUFFIX}
 ${GEM_BIN}/multiruby${GEM_BIN_SUFFIX}
@@ -8,6 +8,7 @@ ${GEM_BIN}/zentest${GEM_BIN_SUFFIX}
 ${GEM_LIB}/cache/${DISTNAME}.gem
 ${GEM_LIB}/gems/${DISTNAME}/
 ${GEM_LIB}/gems/${DISTNAME}/.autotest
+${GEM_LIB}/gems/${DISTNAME}/.gemtest
 ${GEM_LIB}/gems/${DISTNAME}/History.txt
 ${GEM_LIB}/gems/${DISTNAME}/Manifest.txt
 ${GEM_LIB}/gems/${DISTNAME}/README.txt
@@ -31,7 +32,10 @@ ${GEM_LIB}/gems/${DISTNAME}/lib/
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/autoupdate.rb
+${GEM_LIB}/gems/${DISTNAME}/lib/autotest/bundler.rb
+${GEM_LIB}/gems/${DISTNAME}/lib/autotest/isolate.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/once.rb
+${GEM_LIB}/gems/${DISTNAME}/lib/autotest/preload.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/rcov.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/restart.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/autotest/timestamp.rb