diff --git a/www/ruby-rack/Makefile b/www/ruby-rack/Makefile
index 5f8db0258ff..512635496d5 100644
--- a/www/ruby-rack/Makefile
+++ b/www/ruby-rack/Makefile
@@ -1,9 +1,8 @@
-# $OpenBSD: Makefile,v 1.15 2012/09/23 16:57:36 jeremy Exp $
+# $OpenBSD: Makefile,v 1.16 2013/01/18 17:10:09 jeremy Exp $
 
 COMMENT=		modular Ruby webserver interface
 
-DISTNAME=		rack-1.3.6
-REVISION =		0
+DISTNAME=		rack-1.4.4
 CATEGORIES=		www
 
 HOMEPAGE=		http://rack.rubyforge.org/
diff --git a/www/ruby-rack/distinfo b/www/ruby-rack/distinfo
index 25801625cba..caf728d3dc7 100644
--- a/www/ruby-rack/distinfo
+++ b/www/ruby-rack/distinfo
@@ -1,5 +1,2 @@
-MD5 (rack-1.3.6.gem) = Ri/wdEP4L/2Iwbao7c9mWQ==
-RMD160 (rack-1.3.6.gem) = Ms5y1Caj2km/JQle8IrbgdO2tIA=
-SHA1 (rack-1.3.6.gem) = KPugiwdwKlI3daMDHG3iSWN20iM=
-SHA256 (rack-1.3.6.gem) = 1AkPRyBaivTmAr5zz25flPDJGVHPtORoLpP8F7LmcOI=
-SIZE (rack-1.3.6.gem) = 156160
+SHA256 (rack-1.4.4.gem) = f4thsNH2UnlHTwngqS0SHf0NBlGEN1Wg8VLo8CwoHcA=
+SIZE (rack-1.4.4.gem) = 203264
diff --git a/www/ruby-rack/pkg/PLIST b/www/ruby-rack/pkg/PLIST
index 1a0c948099f..eff21e8229c 100644
--- a/www/ruby-rack/pkg/PLIST
+++ b/www/ruby-rack/pkg/PLIST
@@ -1,4 +1,4 @@
-@comment $OpenBSD: PLIST,v 1.7 2011/12/13 17:58:27 jeremy Exp $
+@comment $OpenBSD: PLIST,v 1.8 2013/01/18 17:10:09 jeremy Exp $
 ${GEM_BIN}/rackup${GEM_BIN_SUFFIX}
 ${GEM_LIB}/cache/${DISTNAME}.gem
 ${GEM_LIB}/gems/${DISTNAME}/
@@ -10,7 +10,10 @@ ${GEM_LIB}/gems/${DISTNAME}/SPEC
 ${GEM_LIB}/gems/${DISTNAME}/bin/
 ${GEM_LIB}/gems/${DISTNAME}/bin/rackup
 ${GEM_LIB}/gems/${DISTNAME}/contrib/
+${GEM_LIB}/gems/${DISTNAME}/contrib/rack.png
+${GEM_LIB}/gems/${DISTNAME}/contrib/rack.svg
 ${GEM_LIB}/gems/${DISTNAME}/contrib/rack_logo.svg
+${GEM_LIB}/gems/${DISTNAME}/contrib/rdoc.css
 ${GEM_LIB}/gems/${DISTNAME}/example/
 ${GEM_LIB}/gems/${DISTNAME}/example/lobster.ru
 ${GEM_LIB}/gems/${DISTNAME}/example/protectedlobster.rb
@@ -32,6 +35,7 @@ ${GEM_LIB}/gems/${DISTNAME}/lib/rack/backports/
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/backports/uri/
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/backports/uri/common_18.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/backports/uri/common_192.rb
+${GEM_LIB}/gems/${DISTNAME}/lib/rack/backports/uri/common_193.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/body_proxy.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/builder.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/rack/cascade.rb
@@ -95,12 +99,27 @@ ${GEM_LIB}/gems/${DISTNAME}/test/builder/
 ${GEM_LIB}/gems/${DISTNAME}/test/builder/anything.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/builder/comment.ru
 ${GEM_LIB}/gems/${DISTNAME}/test/builder/end.ru
+${GEM_LIB}/gems/${DISTNAME}/test/builder/line.ru
 ${GEM_LIB}/gems/${DISTNAME}/test/builder/options.ru
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/folder/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/folder/test.js
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/fonts/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/fonts/font.eot
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/images/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/images/image.png
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/index.html
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/javascripts/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/javascripts/app.js
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/stylesheets/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/assets/stylesheets/app.css
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/lighttpd.conf
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/rackup_stub.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/sample_rackup.ru
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/test
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/test+directory/
+${GEM_LIB}/gems/${DISTNAME}/test/cgi/test+directory/test+file
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/test.fcgi
 ${GEM_LIB}/gems/${DISTNAME}/test/cgi/test.ru
 ${GEM_LIB}/gems/${DISTNAME}/test/gemloader.rb
@@ -115,6 +134,9 @@ ${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_and_modification_param
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_escaped_quotes
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_escaped_quotes_and_modification_param
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_percent_escaped_quotes
+${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_unescaped_percentages
+${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_unescaped_percentages2
+${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_unescaped_percentages3
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/filename_with_unescaped_quotes
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/ie
 ${GEM_LIB}/gems/${DISTNAME}/test/multipart/mixed_files
@@ -129,6 +151,7 @@ ${GEM_LIB}/gems/${DISTNAME}/test/registering_handler/
 ${GEM_LIB}/gems/${DISTNAME}/test/registering_handler/rack/
 ${GEM_LIB}/gems/${DISTNAME}/test/registering_handler/rack/handler/
 ${GEM_LIB}/gems/${DISTNAME}/test/registering_handler/rack/handler/registering_myself.rb
+${GEM_LIB}/gems/${DISTNAME}/test/spec_auth.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_auth_basic.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_auth_digest.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_body_proxy.rb
@@ -175,6 +198,10 @@ ${GEM_LIB}/gems/${DISTNAME}/test/spec_thin.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_urlmap.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_utils.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/spec_webrick.rb
+${GEM_LIB}/gems/${DISTNAME}/test/static/
+${GEM_LIB}/gems/${DISTNAME}/test/static/another/
+${GEM_LIB}/gems/${DISTNAME}/test/static/another/index.html
+${GEM_LIB}/gems/${DISTNAME}/test/static/index.html
 ${GEM_LIB}/gems/${DISTNAME}/test/testrequest.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/unregistered_handler/
 ${GEM_LIB}/gems/${DISTNAME}/test/unregistered_handler/rack/