diff --git a/ruby/rb-actionmailer/Portfile b/ruby/rb-actionmailer/Portfile
index e0c989b5965..18d134eeddc 100644
--- a/ruby/rb-actionmailer/Portfile
+++ b/ruby/rb-actionmailer/Portfile
@@ -1,16 +1,21 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        actionmailer 2.2.2 gem {} rubygems
+ruby.setup        actionmailer 6.1.4.1 gem {} rubygems
 categories-append devel
 maintainers       nomaintainer
 description       Simplifies the creation of mail service classes.
 long_description  Simplifies the creation of mail service classes \
                   that uses Action View (from Action Pack) to render \
                   the body templates.
-checksums           md5     bd50366a8bd2a88d0e312241c4123028 \
-                    sha1    a7f3d228cdc763886fd1fe8b5637c56795df3fd0 \
-                    rmd160  9f896948661bbf66e0ec26dded72eced17ae8451
+checksums           rmd160  e02f753f4acca902b2337bb28fd5e0469f55ab56 \
+                    sha256  229525238eeba137d9ecdc6c331fac07c76a2305ea66f102642f16a6043d4003 \
+                    size    30720
 platforms         darwin
 
-depends_lib-append  port:rb-actionpack
+depends_lib-append  port:rb-actionpack \
+                    port:rb${ruby.suffix}-actionview \
+                    port:rb${ruby.suffix}-activejob \
+                    port:rb${ruby.suffix}-activesupport \
+                    port:rb${ruby.suffix}-mail \
+                    port:rb${ruby.suffix}-rails-dom-testing
diff --git a/ruby/rb-actionpack/Portfile b/ruby/rb-actionpack/Portfile
index 5e671d7873b..64c8e977479 100644
--- a/ruby/rb-actionpack/Portfile
+++ b/ruby/rb-actionpack/Portfile
@@ -1,7 +1,7 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        actionpack 2.2.2 gem {} rubygems
+ruby.setup        actionpack 6.1.4.1 gem {} rubygems
 categories-append devel
 maintainers       nomaintainer
 description       Eases web-request routing, handling, and response.
@@ -9,9 +9,16 @@ long_description  Eases web-request routing, handling, and response as a \
                   half-way front, half-way page controller. Implemented \
                   with specific emphasis on enabling easy unit/integration \
                   testing that doesn't require a browser.
-checksums           md5     a2764a85d8d34385467d8f9df7362471 \
-                    sha1    02b9aec25f90e6237487aa981d993760ce4a3869 \
-                    rmd160  d7e78b64a5c3ec616a11dd08a96a33de91bf936b
+checksums           rmd160  0947de22e1872ad499cd5ce91361ffc9e5c307eb \
+                    sha256  2a5e0af9f561e8b7f27b1f4088a3d6d4283ec7eaa283f0db345ecb152dd6fe75 \
+                    size    225280
 platforms         darwin
 
-depends_lib-append  port:rb-activesupport
+depends_lib-append  port:rb-activesupport \
+                    port:rb${ruby.suffix}-actionview \
+                    port:rb${ruby.suffix}-rack \
+                    port:rb${ruby.suffix}-rack-test \
+                    port:rb${ruby.suffix}-rails-dom-testing \
+                    port:rb${ruby.suffix}-rails-html-sanitizer
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-activemodel
diff --git a/ruby/rb-activerecord/Portfile b/ruby/rb-activerecord/Portfile
index fe43c1c0a7f..a0c507d82e8 100644
--- a/ruby/rb-activerecord/Portfile
+++ b/ruby/rb-activerecord/Portfile
@@ -1,7 +1,7 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        activerecord 2.2.2 gem {} rubygems
+ruby.setup        activerecord 6.1.4.1 gem {} rubygems
 
 categories-append devel
 maintainers       nomaintainer
@@ -13,9 +13,10 @@ long_description  Implements the ActiveRecord pattern (Fowler, PoEAA) for \
                   can find, save, and destroy themselves without resorting \
                   to manual SQL.
                   
-checksums           md5     c0856ff382bd0527ceb7b462730fa9f2 \
-                    sha1    d0874b767d91a644502ece68e36e8b3ba657625b \
-                    rmd160  92bbc542062f0a1228600e2e1482aea65f9ce135
+checksums           rmd160  9b51c13a8939ee5bb0f2e3949281e3f07b32c784 \
+                    sha256  4a22709593cf8e164939286bc1635efcd87378244ad17e87becb1f7324dd8fb1 \
+                    size    430592
 platforms         darwin
 
-depends_lib-append  port:rb-activesupport
+depends_lib-append  port:rb-activesupport \
+                    port:rb${ruby.suffix}-activemodel
diff --git a/ruby/rb-activeresource/Portfile b/ruby/rb-activeresource/Portfile
index b76c2f7ab7a..c010caecc6f 100644
--- a/ruby/rb-activeresource/Portfile
+++ b/ruby/rb-activeresource/Portfile
@@ -1,7 +1,7 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        activeresource 2.2.2 gem {} rubygems
+ruby.setup        activeresource 5.1.1 gem {} rubygems
 
 categories-append devel
 license           MIT
@@ -10,9 +10,14 @@ maintainers       nomaintainer
 description       Object-oriented REST services
 long_description  ${description}
                   
-checksums           md5     c81f4bc9f3fcb5e7480b69e5c9a4f2ee \
-                    sha1    03f83fe6227d812465931b6724a113b52548d558 \
-                    rmd160  6205f2b42871ff26e0119e3664dd92bc24cbe179
+checksums           rmd160  c3586037b42f7763b07274b04450ddb56e9a697b \
+                    sha256  63dbaa2f29a12c328ba7af1b89198678ffa3c3d34891e91935caeb46bee021df \
+                    size    41472
 platforms         darwin
 
-depends_lib-append  port:rb-activesupport
+depends_lib-append  port:rb-activesupport \
+                    port:rb${ruby.suffix}-activemodel \
+                    port:rb${ruby.suffix}-activemodel-serializers-xml
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-mocha \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-activesupport/Portfile b/ruby/rb-activesupport/Portfile
index b2e6a5aac07..155889acd9e 100644
--- a/ruby/rb-activesupport/Portfile
+++ b/ruby/rb-activesupport/Portfile
@@ -1,7 +1,7 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        activesupport 2.2.2 gem {} rubygems
+ruby.setup        activesupport 6.1.4.1 gem {} rubygems
 
 categories-append devel
 license           MIT BSD
@@ -11,7 +11,13 @@ description       Ruby utility classes and extension to the standard library.
 long_description  Utility classes and extension to the standard library \
                   that were required by Rails, but found of general use.
                   
-checksums         md5     2251cb08f36e40bb48ea3bb805323cc7 \
-                  sha1    4fc82b0c7f8f38879c593a722cdd788f876a1868 \
-                  rmd160  6064300c37ac2a542d87019fd485b5877c379b2e
+checksums         rmd160  ede0859be6d34260e5954b951410ddfcc890b4b8 \
+                  sha256  44b781877c2189aa15ca5451e2d310dcedfd16c01df1106f68a91b82990cfda5 \
+                  size    219648
 platforms         darwin
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-concurrent-ruby \
+                   port:rb${ruby.suffix}-i18n \
+                   port:rb${ruby.suffix}-minitest \
+                   port:rb${ruby.suffix}-tzinfo \
+                   port:rb${ruby.suffix}-zeitwerk
diff --git a/ruby/rb-archive-tar-minitar/Portfile b/ruby/rb-archive-tar-minitar/Portfile
index 57fb39ececd..ea940aa94ea 100644
--- a/ruby/rb-archive-tar-minitar/Portfile
+++ b/ruby/rb-archive-tar-minitar/Portfile
@@ -1,8 +1,8 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		archive-tar-minitar 0.5.2 gem {} rubygems
-revision		1
+ruby.setup		archive-tar-minitar 0.8 gem {} rubygems
+revision		0
 maintainers		nomaintainer
 description		Ruby library and command line utility to deal with POSIX tar archive files.
 long_description	Archive::Tar::Minitar is a pure-Ruby library and \
@@ -13,5 +13,10 @@ long_description	Archive::Tar::Minitar is a pure-Ruby library and \
                     been reorganised to promote reuse in other projects.
 categories-append	archivers
 license			{Ruby GPL-2}
-checksums		md5 c8bf480d64cd6be11c0670870dbd760c
+checksums		rmd160  1f93760bc353f4893a14d7ba91a7ad01d1b33151 \
+           sha256  9d80e397f112133bffc468fb1042baade21417aa1f85fdbb956d66eab3275986 \
+           size    5120
 platforms		darwin
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-minitar \
+                   port:rb${ruby.suffix}-minitar-cli
diff --git a/ruby/rb-bee/Portfile b/ruby/rb-bee/Portfile
index 888df45727a..31fb16462bc 100644
--- a/ruby/rb-bee/Portfile
+++ b/ruby/rb-bee/Portfile
@@ -1,8 +1,8 @@
 PortSystem 1.0
 PortGroup ruby 1.0
 
-ruby.setup		bee 0.5.1 gem {} rubygems
-revision        1
+ruby.setup		bee 0.12.2 gem {} rubygems
+revision        0
 
 categories-append	devel
 license			Apache
@@ -14,11 +14,13 @@ long_description	Bee is a build tool running YAML files. \
 			and run as fast as make. They are made of shell \
 			commands, Ruby code or Bee tasks for platform \
 			independent builds.
-checksums		md5     502d8091613409c3c8de1667ac501c7e \
-			sha1    f6b13b22a01512649a8b6b8c625dde5a1433057d \
-			rmd160  fa044db0632b3711e0b715e2d83364ea1ef3d772
+checksums		rmd160  dd3500e4f59589a2d95d7d938ea7721cdf2d7b5f \
+           sha256  7860a26a7ffbc1968fb10ee3b07fd1015754ec3f3ca697ff7c440dad906207ef \
+           size    53248
 depends_run		port:rb-archive-tar-minitar port:rb-rubyzip
 
 
 universal_variant no
 
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-highline
diff --git a/ruby/rb-bones/Portfile b/ruby/rb-bones/Portfile
index b0cc27a81e0..404227c71e0 100644
--- a/ruby/rb-bones/Portfile
+++ b/ruby/rb-bones/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          bones 2.5.1 gem {} rubygems
-revision            1
+ruby.setup          bones 3.8.5 gem {} rubygems
+revision            0
 
 maintainers         nomaintainer
 categories-append   devel
@@ -12,6 +12,12 @@ long_description    ${description}
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 a79ec53b36af5afba62ae328062a92fc \
-                    rmd160 6b78d134a03209c39b6bf4560fa1d9820c023e01 \
-                    sha1 4b17b691ee2c76f45cf03af85a269e8ba3a15f0a
+checksums           rmd160  93ede0362494107fba1270ab2d0650f33d5f1ae7 \
+                    sha256  5e463d7e0946f86a25c0c20bc33d92e52ccc9774d4d00438f9279c6dd984c430 \
+                    size    39936
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-little-plugger \
+                   port:rb${ruby.suffix}-loquacious \
+                   port:rb${ruby.suffix}-rdoc
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rspec
diff --git a/ruby/rb-builder/Portfile b/ruby/rb-builder/Portfile
index bb6406a2bba..fb744d4710e 100644
--- a/ruby/rb-builder/Portfile
+++ b/ruby/rb-builder/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			builder 2.1.2 gem {} rubygems
+ruby.setup			builder 3.2.4 gem {} rubygems
 license				MIT
 maintainers			nomaintainer
 description			Builders for MarkUp.
@@ -9,9 +9,9 @@ long_description	Builder provides a number of builder objects that make \
 					creating structured data simple to do.  Currently the \
 					following builder objects are supported:  * XML Markup * \
 					XML Events
-checksums			md5 e96a525d9e0b42a2e2d5e77cbd02eb72 \
-					sha1 d0ea89ea793c75853abd636ab86a79b7b57d6993 \
-					rmd160 73f0b0b5d0c2d268edbcee86599962cc94413ebb
+checksums			rmd160  38f46a8f4796958990e8196894decede85a1375a \
+            sha256  99caf08af60c8d7f3a6b004029c4c3c0bdaebced6c949165fe98f1db27fbbc10 \
+            size    32256
 platforms			darwin
 
 livecheck.version	BUILDER-${version}
diff --git a/ruby/rb-bundler/Portfile b/ruby/rb-bundler/Portfile
index 710c11ecf74..dcda1761c47 100644
--- a/ruby/rb-bundler/Portfile
+++ b/ruby/rb-bundler/Portfile
@@ -4,10 +4,10 @@ PortSystem          1.0
 PortGroup           ruby 1.0
 
 ruby.branches       1.9 2.3 2.4 2.5
-ruby.setup          bundler 2.2.15 gem
-checksums           rmd160  709edc8f045fd2e558491909945059493f09ce33 \
-                    sha256  9295b52d6744076497b86a7dfe03ffa4599942f245558c98071b8a05e3535835 \
-                    size    389120
+ruby.setup          bundler 2.2.27 gem
+checksums           rmd160  a3d36a129a144775233856d2bab1e96a42e0de0f \
+                    sha256  21d85c47937496b08b021df716b4eaa81e2223a04e8eba92ee9e767b9e1b3ed8 \
+                    size    391680
 
 license             MIT
 categories-append   www devel
diff --git a/ruby/rb-capistrano/Portfile b/ruby/rb-capistrano/Portfile
index 2d8adde1cc5..51c76a3d477 100644
--- a/ruby/rb-capistrano/Portfile
+++ b/ruby/rb-capistrano/Portfile
@@ -1,15 +1,15 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          capistrano 2.5.21 gem {} rubygems
+ruby.setup          capistrano 3.16.0 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         Capistrano is a utility and framework for executing \
                     commands in parallel on multiple remote machines, via SSH.
 long_description    ${description}
-checksums           md5     be5ac7a64974207bebe55da857e6319c \
-                    sha1    110a78346212a304b625fd4acad1eda1c0819bd8 \
-                    rmd160  05d9f453a5272f6cc2d1c4c43989a2800a5e5e94
+checksums           rmd160  51be3de3ad9a7b0ad5f56114c8ace3447c819aa2 \
+                    sha256  a3abd38bef210e2a921ff8bf41fb4d7328db96168cf89eefb4377295c50f80cb \
+                    size    69120
 platforms           darwin
 homepage            https://capistranorb.com
 
@@ -19,3 +19,11 @@ depends_run         port:rb-net-ssh \
                     port:rb-net-ssh-gateway \
                     port:rb-highline \
                     port:rb-mocha
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-airbrussh \
+                   port:rb${ruby.suffix}-i18n \
+                   port:rb${ruby.suffix}-rake \
+                   port:rb${ruby.suffix}-sshkit
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-rubocop
diff --git a/ruby/rb-cmdparse/Portfile b/ruby/rb-cmdparse/Portfile
index d878e4a74d5..03d914c8cee 100644
--- a/ruby/rb-cmdparse/Portfile
+++ b/ruby/rb-cmdparse/Portfile
@@ -2,7 +2,7 @@ PortSystem      1.0
 PortGroup       ruby 1.0
 
 ruby.branches   2.7 2.6
-ruby.setup      cmdparse 3.0.6 gem
+ruby.setup      cmdparse 3.0.7 gem
 
 maintainers     {kimuraw @kimuraw} openmaintainer
 description     cmdparse - advanced command line parser supporting commands
@@ -14,8 +14,8 @@ categories-append   devel
 homepage        https://cmdparse.gettalong.org/
 license         MIT
 supported_archs noarch
-checksums       md5 31a0c3badc423217188497568841a4c3 \
-                sha1 d2c1489e2b1e226f9eafe6301537163d29cf6571 \
-                rmd160 232a9b60f5cf5f793eda53df194db2658b59cdf8
+checksums       rmd160  66f869b6d6555ad2af3b4984d2a970eb2ae26ff4 \
+                sha256  f7c5cace10bec6abf853370ae095e4b97a84ed9d847b3fb38f41cc4fbc950739 \
+                size    54784
 platforms       darwin
 
diff --git a/ruby/rb-coderay/Portfile b/ruby/rb-coderay/Portfile
index dea9246a067..7e4d193c8d3 100644
--- a/ruby/rb-coderay/Portfile
+++ b/ruby/rb-coderay/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			coderay 0.9.8 gem {} rubygems
+ruby.setup			coderay 1.1.3 gem {} rubygems
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			Fast and easy syntax highlighting for selected languages.
 long_description	Fast and easy syntax highlighting for selected languages, \
@@ -11,8 +11,8 @@ homepage			http://coderay.rubychan.de/
 license				LGPL-2.1+
 supported_archs		noarch
 
-checksums			md5     9e0e0cba383daba57ef7c256a1742965 \
-					sha1    36bb1b8aa8f0f1285ab912d7f13690bef19da3c6 \
-					rmd160  82e8c8d9da56ea47785486e26d4e873e602b06ee
+checksums			rmd160  802758086e7f5fc632720de7693c855a622a4b91 \
+            sha256  dc530018a4684512f8f38143cd2a096c9f02a1fc2459edcfe534787a7fc77d4b \
+            size    92672
 platforms			darwin
 
diff --git a/ruby/rb-compass/Portfile b/ruby/rb-compass/Portfile
index aa1edf01088..33af74a913b 100644
--- a/ruby/rb-compass/Portfile
+++ b/ruby/rb-compass/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          compass 0.12.2 gem {} rubygems
+ruby.setup          compass 1.0.3 gem {} rubygems
 revision            0
 maintainers         nomaintainer
 description         Stylesheet authoring frameworking
@@ -16,7 +16,13 @@ license             MIT
 platforms           darwin
 homepage            http://compass-style.org/
 
-checksums           rmd160  5c80ce506801f2e1d422b863b2796cc29b3e085e \
-                    sha256  5f9784fcc40e1535b81e66e57d2e0d898f1a00099dd455a35dbb21fbb40f4a3b
+checksums           rmd160  d511e00d6ba60a15bfe99114876c88df8ac31820 \
+                    sha256  4c7884dc5349d59011fd6c5736a0404008d5609235037741feac9c8ff840d151 \
+                    size    378368
 
 depends_run         path:bin/haml:rb-haml
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-compass-core \
+                   port:rb${ruby.suffix}-compass-import-once \
+                   port:rb${ruby.suffix}-rb-fsevent \
+                   port:rb${ruby.suffix}-rb-inotify
diff --git a/ruby/rb-configuration/Portfile b/ruby/rb-configuration/Portfile
index 3c6d08ef967..f0840fcd3a5 100644
--- a/ruby/rb-configuration/Portfile
+++ b/ruby/rb-configuration/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          configuration 1.1.0 gem {} rubygems
+ruby.setup          configuration 1.3.4 gem {} rubygems
 
 maintainers         nomaintainer
 categories-append   devel
@@ -12,6 +12,6 @@ homepage            https://github.com/ahoward/configuration/tree/master
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 1b032ac8bd21277e048b10ca0f487a0a \
-                    rmd160 62706752fa92fc6762df44192ab907a2040e5b2b \
-                    sha1 7b5ffc98f756b815507990b825df383b01542878
+checksums           rmd160  7724d1c6b5ae87d1fe7c26651c9509655370eab0 \
+                    sha256  e9f3ea332ec46e2da4df162e29c4f064d620d5cd6bd157d267b6379c267b8e21 \
+                    size    11776
diff --git a/ruby/rb-crypt-isaac/Portfile b/ruby/rb-crypt-isaac/Portfile
index 78274e887db..1530cfd31d7 100644
--- a/ruby/rb-crypt-isaac/Portfile
+++ b/ruby/rb-crypt-isaac/Portfile
@@ -1,7 +1,7 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		crypt-isaac 0.9.1 gem {} rubygems
+ruby.setup		crypt-isaac 1.2.0 gem {} rubygems
 maintainers		nomaintainer
 description		Implementation of the ISAAC psuedo random number generator.
 long_description	This is a Ruby implementation of the ISAAC \
@@ -10,6 +10,12 @@ long_description	This is a Ruby implementation of the ISAAC \
                     quality random numbers.
 
 categories-append   security
-checksums		    md5 e6443702be1b114bb87b867b621f7ada
+checksums		    rmd160  42de41b18e2a167aec1d07adab72fc83705fe2db \
+               sha256  4a5e48e279e4338c843e934dc58b049f74f562bbbeea54a9da694ef6196168d7 \
+               size    17408
 platforms		    darwin
 supported_archs	    noarch
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-cucumber/Portfile b/ruby/rb-cucumber/Portfile
index 2386ff47c37..62604c55e63 100644
--- a/ruby/rb-cucumber/Portfile
+++ b/ruby/rb-cucumber/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          cucumber 0.3.103 gem {} rubygems
+ruby.setup          cucumber 7.0.0 gem {} rubygems
 
 license             MIT
 maintainers         nomaintainer
@@ -11,9 +11,35 @@ long_description    ${description}
 homepage            http://cukes.info
 platforms           darwin
 
-depends_lib-append  port:rb-term-ansicolor port:rb-treetop port:rb-polyglot \
-                    port:rb-diff-lcs port:rb-builder
+depends_lib-append  port:rb-term-ansicolor \
+                    port:rb-treetop \
+                    port:rb-polyglot \
+                    port:rb-diff-lcs \
+                    port:rb-builder \
+                    port:rb${ruby.suffix}-cucumber-core \
+                    port:rb${ruby.suffix}-cucumber-create-meta \
+                    port:rb${ruby.suffix}-cucumber-cucumber-expressions \
+                    port:rb${ruby.suffix}-cucumber-gherkin \
+                    port:rb${ruby.suffix}-cucumber-html-formatter \
+                    port:rb${ruby.suffix}-cucumber-messages \
+                    port:rb${ruby.suffix}-cucumber-wire \
+                    port:rb${ruby.suffix}-mime-types \
+                    port:rb${ruby.suffix}-multi_test \
+                    port:rb${ruby.suffix}-sys-uname
 
-checksums           md5 1c78cebc78ec1a47791ea109a4d5d1b8 \
-                    rmd160 ed7b0903acc778852a8b5ce1e9ee75cf49a53179 \
-                    sha1 b17c309fb3ea1506f62212235d007f02e9584960
+checksums           rmd160  0fea8fe48a6673d00ef5afb7d5a253b60f84e6ed \
+                    sha256  07c7ddb6e4d5518034e4307d67c75f4f0f2bda6bf23c95a5d9b7b87cda23e2fa \
+                    size    128000
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-capybara \
+                    port:rb${ruby.suffix}-nokogiri \
+                    port:rb${ruby.suffix}-octokit \
+                    port:rb${ruby.suffix}-pry \
+                    port:rb${ruby.suffix}-rack-test \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-simplecov \
+                    port:rb${ruby.suffix}-sinatra \
+                    port:rb${ruby.suffix}-syntax \
+                    port:rb${ruby.suffix}-test-unit \
+                    port:rb${ruby.suffix}-webrick
diff --git a/ruby/rb-daemons/Portfile b/ruby/rb-daemons/Portfile
index 9ed9bdade8f..6d06335b1c6 100644
--- a/ruby/rb-daemons/Portfile
+++ b/ruby/rb-daemons/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			daemons 1.1.0 gem {} rubygems
+ruby.setup			daemons 1.4.1 gem {} rubygems
 maintainers			nomaintainer
 description			A toolkit to create and control daemons in different ways
 long_description	Daemons provides an easy way to wrap existing ruby \
@@ -14,9 +14,14 @@ long_description	Daemons provides an easy way to wrap existing ruby \
 					exception  backtracing and logging (in case your ruby \
 					script crashes) and monitoring and automatic restarting \
 					of your processes if they crash.
-checksums			md5 6c50720bab6a19d88b401a98a79c49ce \
-					sha1 6f1a7d04bffc49c629ce4e6cd7b9f17acfb1def5 \
-					rmd160 207f325a5dd5119f559c0909d68747aaaa28f4c4
+checksums			rmd160  171926eb891f20afac37b4fb22f92efb77933c02 \
+            sha256  8fc76d76faec669feb5e455d72f35bd4c46dc6735e28c420afb822fac1fa9a1d \
+            size    29696
 platforms           darwin
 license				Ruby
 homepage			https://github.com/thuehlinger/daemons
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-pry-byebug \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-simplecov
diff --git a/ruby/rb-diff-lcs/Portfile b/ruby/rb-diff-lcs/Portfile
index bf1e92e3ee7..5106220281f 100644
--- a/ruby/rb-diff-lcs/Portfile
+++ b/ruby/rb-diff-lcs/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          diff-lcs 1.1.2 gem {} rubygems
-revision            1
+ruby.setup          diff-lcs 1.4.4 gem {} rubygems
+revision            0
 
 maintainers         nomaintainer
 license             {GPL-2+ Artistic-1 Ruby}
@@ -11,6 +11,15 @@ long_description    ${description}
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 60524d29b37f76d56ce835323e324879 \
-                    rmd160 f57dcbd09658cea31f286039ec3f0b599c99ff25 \
-                    sha1 05a1164be2de3555104af79791da2977e6419d59
+checksums           rmd160  93a54bba68b26ca49cbd676735ef3a4f109b213b \
+                    sha256  bf3a658875f70c1467fe7a3b302b795f074c84b28db6e4a2bd6b1ad6d12a2255 \
+                    size    50688
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-hoe \
+                    port:rb${ruby.suffix}-hoe-doofus \
+                    port:rb${ruby.suffix}-hoe-gemspec2 \
+                    port:rb${ruby.suffix}-hoe-git \
+                    port:rb${ruby.suffix}-hoe-rubygems \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc \
+                    port:rb${ruby.suffix}-rspec
diff --git a/ruby/rb-dnssd/Portfile b/ruby/rb-dnssd/Portfile
index 9965a90b5d0..b2b911c23bf 100644
--- a/ruby/rb-dnssd/Portfile
+++ b/ruby/rb-dnssd/Portfile
@@ -1,7 +1,7 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		dnssd 2.0 gem {} rubygems
+ruby.setup		dnssd 3.0.1 gem {} rubygems
 description		DNS Service Discovery (aka Bonjour) API for Ruby
 long_description DNS Service Discovery (aka Bonjour, MDNS) API for Ruby. \
 				Implements browsing, resolving, registration and domain  \
@@ -12,7 +12,9 @@ license			Ruby
 maintainers		{kimuraw @kimuraw} openmaintainer
 
 platforms		darwin
-checksums		md5 04b1ade4d75ab93f4942c960dce2000d \
-				rmd160 d1f73eab1d39f6fa277bced5fe18d487688c78df \
-				sha1 bc756d287cd91bca8e27ffd6c2fb2b0c8b65887c
+checksums		rmd160  1a0c33056750499a4addef52090c7f59bdb18cad \
+           sha256  3167a06edd3376930facf0bb015407ae755868691d38039be23baad0d6c7cebf \
+           size    31744
 
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-eventmachine/Portfile b/ruby/rb-eventmachine/Portfile
index 21f86ca6690..bcfaf70c68b 100644
--- a/ruby/rb-eventmachine/Portfile
+++ b/ruby/rb-eventmachine/Portfile
@@ -1,8 +1,8 @@
 PortSystem		    1.0
 PortGroup		    ruby 1.0
-revision			1
+revision			0
 
-ruby.setup          eventmachine 0.12.10 gem {} rubygems
+ruby.setup          eventmachine 1.2.7 gem {} rubygems
 description		    fast, simple event-processing library for Ruby programs
 long_description	\
     EventMachine implements a fast, single-threaded engine for arbitrary \
@@ -21,7 +21,11 @@ maintainers		    {kimuraw @kimuraw} openmaintainer
 homepage		    http://rubyeventmachine.com/
 categories-append   devel
 platforms           darwin
-checksums           md5     1379ea93ad77132fb3756b492025f172 \
-                    sha1    d9b3ec65e3e94e461ed2d53c01a2b9ab62fe6a07 \
-                    rmd160  625b4917e84d55fec468a810e9ee0bb5273387f0
+checksums           rmd160  4e9d691560f4ba023e7c7bbc9d8e3343e2011ec8 \
+                    sha256  11ab7af3505f53ed7565d6a13fe73568fe0d6fac647c8816430e9c3171c8c58f \
+                    size    262144
 
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rake-compiler \
+                    port:rb${ruby.suffix}-rake-compiler-dock \
+                    port:rb${ruby.suffix}-test-unit
diff --git a/ruby/rb-ferret/Portfile b/ruby/rb-ferret/Portfile
index 5b8d1ebff4d..951115c74d3 100644
--- a/ruby/rb-ferret/Portfile
+++ b/ruby/rb-ferret/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          ferret 0.11.8.5 gem {} rubygems
+ruby.setup          ferret 0.11.8.7 gem {} rubygems
 categories-append   devel textproc
 license             MIT BSD
 maintainers         nomaintainer
@@ -12,6 +12,6 @@ long_description \
 
 platforms           darwin
 
-checksums           md5     a64c5d3b051750339ab9791790965df2 \
-                    sha1    6ee34ae8386283936d416dd8944a5cdd320272c0 \
-                    rmd160  2b49bc0d92cbcb91c2ec5d6ed79b65cb37549828
+checksums           rmd160  cd7ed8539dd4ab06700816d90f0408db081575de \
+                    sha256  9b22927618fbc76579665ea4cc4133edeeff8d31c2b974507f59078042048363 \
+                    size    608768
diff --git a/ruby/rb-flexmock/Portfile b/ruby/rb-flexmock/Portfile
index 4ca3afe58de..557af1a40f7 100644
--- a/ruby/rb-flexmock/Portfile
+++ b/ruby/rb-flexmock/Portfile
@@ -2,7 +2,7 @@ PortSystem			1.0
 PortGroup			ruby 1.0
 PortGroup           github 1.0
 
-github.setup        jimweirich flexmock 0.8.11 flexmock-
+github.setup        jimweirich flexmock 2.3.6 flexmock-
 ruby.setup			flexmock 0.8.11 basic_install.rb {}
 
 categories-append	devel
@@ -13,9 +13,9 @@ description			FlexMock is a flexible mocking library for use in unit testing and
 long_description	FlexMock is a flexible mocking library for use in unit testing and behavior specification. \
 					Mocks are defined with a fluent API that makes mock specifications easy to read and easy to remember.
 
-checksums			md5 cc034dcf5f977f739627187ac6cfc203 \
-					sha1 0b62119a7485754a6b81990338afcb745e422aa0 \
-					rmd160 12b906eac11a4c288bf87675c2765794aa07cf09
+checksums			rmd160  cd901eba40b9ba215295e7639844c39339e6caa8 \
+            sha256  b5aa6dc338148be8c80f3b2a7ab57b668bacc748f66032b29eaabb533e85851e \
+            size    67584
 
 patchfiles			patch-install.rb
 
@@ -26,3 +26,8 @@ destroot.args		""
 destroot.env		DESTDIR=${destroot}
 
 depends_lib			port:ruby
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-coveralls \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-simplecov
diff --git a/ruby/rb-flickr/Portfile b/ruby/rb-flickr/Portfile
index fc898f54cc4..37e7f3bdea7 100644
--- a/ruby/rb-flickr/Portfile
+++ b/ruby/rb-flickr/Portfile
@@ -1,17 +1,25 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			flickr 1.0.0 gem {} rubygems
+ruby.setup			flickr 2.0.2 gem {} rubygems
 license				MIT
 maintainers			nomaintainer
 platforms			darwin
 description			An insanely easy interface to the Flickr photo-sharing \
 					service. By Scott Raymond.
 long_description	${description}
-checksums			md5 b1b853bff90ca4c98dd055e9339a09f3 \
-					sha1 9192b06d9d765c15f5e2a70b25c8fd474c76831e \
-					rmd160 07fd1a1ba9860f4a933c1ce838fd4062610291db
+checksums			rmd160  8ed6ef8e3463c25e9b59dfe170cb0f488090642b \
+            sha256  76aa357d925acde012f423b9723522cb6c55873a204efa7a5c876258816e9bb5 \
+            size    17408
 homepage			http://redgreenblu.com/flickr/
 
 depends_lib-append \
 					port:rb-xml-simple
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler-audit \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-nokogiri \
+                    port:rb${ruby.suffix}-pry \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-vcr \
+                    port:rb${ruby.suffix}-webmock
diff --git a/ruby/rb-fxruby/Portfile b/ruby/rb-fxruby/Portfile
index 1c257c4712a..3934ad2dcb3 100644
--- a/ruby/rb-fxruby/Portfile
+++ b/ruby/rb-fxruby/Portfile
@@ -3,20 +3,21 @@
 PortSystem      1.0
 PortGroup       ruby 1.0
 
-ruby.setup          fxruby 1.6.24 gem {} rubygems
+ruby.setup          fxruby 1.6.44 gem {} rubygems
 maintainers         nomaintainer
 description         Ruby bindings for the FOX GUI Toolkit.
 long_description    FXRuby is a Ruby extention module that provides an \
                     interface to the FOX GUI library.
 categories-append   x11
 homepage            http://www.fxruby.org
-checksums           md5     b749cfde23d4120960d0a958f427283c \
-                    sha1    970f9f165f4c95b722845ecc6739b60816d0777a \
-                    rmd160  21af4dfc0d28b64583f10b72e7d0b9c54fc27ab7
+checksums           rmd160  dfbd50bb0d69a82d44f685189f9760b4f6cd7631 \
+                    sha256  cd57a530d26b0785c916d8fb037bf2bdecf283c4f9a5d8c7b295293d68aa74e6 \
+                    size    3246592
 platforms           darwin
 depends_lib-append  port:fox \
                     port:fxscintilla \
-                    port:rb-hoe
+                    port:rb-hoe \
+                    port:rb${ruby.suffix}-mini_portile2
 # fix permission
 post-destroot {
     system -W "${workpath}/${distname}" \
diff --git a/ruby/rb-getopt-declare/Portfile b/ruby/rb-getopt-declare/Portfile
index 24244e2d27e..6ee236cb3dd 100644
--- a/ruby/rb-getopt-declare/Portfile
+++ b/ruby/rb-getopt-declare/Portfile
@@ -1,8 +1,8 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		getopt-declare 1.09.7 gem {} rubygems
-revision		2
+ruby.setup		getopt-declare 1.32 gem {} rubygems
+revision		0
 license			Artistic-1 Permissive
 maintainers		nomaintainer
 description		Declaratively Expressed Command-Line Arguments via RegExp
@@ -11,5 +11,7 @@ long_description	Getopt::Declare is yet another command-line argument \
 					powerful but exceptionally easy to use. It supports \
 					many options not supported by optparser or \
 					getoptlong as well as it has a simpler syntax.
-checksums		md5 ae54a2a6a228e23d247c45ff35b2dd4f
+checksums		rmd160  b9a7d4feab4d54554de79ee8c546a34066d5bd5e \
+           sha256  0654be85f090e4b2e1b9f1b04fcf55495eda65847bd522987e1a60e3b65ae8ce \
+           size    50176
 platforms		darwin
diff --git a/ruby/rb-haml-edge/Portfile b/ruby/rb-haml-edge/Portfile
index cdf6ef1399d..8dc7c0fecdc 100644
--- a/ruby/rb-haml-edge/Portfile
+++ b/ruby/rb-haml-edge/Portfile
@@ -1,9 +1,9 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          haml-edge 2.3.251 gem
+ruby.setup          haml-edge 3.1.79 gem
 conflicts           rb-haml
-revision            1
+revision            0
 maintainers         nomaintainer
 description         Haml and Sass: markup languages for HTML and CSS (bleeding edge)
 long_description    \
@@ -22,6 +22,6 @@ license             MIT
 platforms           darwin
 homepage            http://haml-lang.com
 master_sites        http://rubygems.org/downloads/
-checksums           md5     649a903fd30b12513f97403e2b45b102 \
-                    sha1    143d032ef3a1a7920b39d370ca5832179065523c \
-                    rmd160  97bba5374c52d8b75985ed130405041351474b62
+checksums           rmd160  7c9ff41a88ac57e5effd0e6c0b9ee41db78872b9 \
+                    sha256  247fad8652157de15bbc3d1354b13663fe061540a5cfe1ed5d54046be89f1274 \
+                    size    278528
diff --git a/ruby/rb-haml/Portfile b/ruby/rb-haml/Portfile
index d3677c21b54..6ce4317153d 100644
--- a/ruby/rb-haml/Portfile
+++ b/ruby/rb-haml/Portfile
@@ -1,9 +1,9 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          haml 3.0.25 gem
+ruby.setup          haml 5.2.2 gem
 conflicts           rb-haml-edge
-revision            1
+revision            0
 maintainers         nomaintainer
 description         Haml and Sass: markup languages for HTML and CSS
 long_description    \
@@ -22,6 +22,15 @@ license             MIT
 platforms           darwin
 homepage            http://haml-lang.com
 master_sites        http://rubygems.org/downloads/
-checksums           md5     88da935b08a8458d453a65da1a93f4de \
-                    sha1    71fba1c7deefc237af6712388b1240aeed5e2113 \
-                    rmd160  5c34251668d422d2d75480f44ba06fc38c90e2a6
+checksums           rmd160  a45693407969c4b2ba567e65709757358ad97d8e \
+                    sha256  6e759246556145642ef832d670fc06f9bd8539159a0e600847a00291dd7aae0c \
+                    size    92160
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-temple \
+                   port:rb${ruby.suffix}-tilt
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-nokogiri \
+                    port:rb${ruby.suffix}-rails \
+                    port:rb${ruby.suffix}-rbench \
+                    port:rb${ruby.suffix}-simplecov
diff --git a/ruby/rb-highline/Portfile b/ruby/rb-highline/Portfile
index 30bd6aa85ab..70706645b56 100644
--- a/ruby/rb-highline/Portfile
+++ b/ruby/rb-highline/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          highline 1.5.2 gem {} rubygems
+ruby.setup          highline 2.0.3 gem {} rubygems
 maintainers         nomaintainer
 description         A high-level IO library.
 long_description    A high-level IO library that provides validation, type \
@@ -11,8 +11,12 @@ long_description    A high-level IO library that provides validation, type \
                     with just minutes of work.
 license             {GPL-2 Ruby}
 supported_archs     noarch
-checksums           md5     10940b08add2173252b267d1919cd5b6 \
-                    sha1    2b1d6b3088d91df2fd955928731fb0aabdb3817f \
-                    rmd160  4994a380da10d1938424aa8062b508208edc32cf
+checksums           rmd160  f0631d366164ee92368d6ca8976a5d093b0efcfd \
+                    sha256  2ddd5c127d4692721486f91737307236fe005352d12a4202e26c48614f719479 \
+                    size    216576
 platforms           darwin
 homepage            https://github.com/JEG2/highline
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-hoe/Portfile b/ruby/rb-hoe/Portfile
index 75c92ef91f2..7c317f5d105 100644
--- a/ruby/rb-hoe/Portfile
+++ b/ruby/rb-hoe/Portfile
@@ -1,7 +1,7 @@
 PortSystem 1.0
 PortGroup			ruby 1.0
 
-ruby.setup			hoe 3.13.1 gem {} rubygems
+ruby.setup			hoe 3.23.0 gem {} rubygems
 maintainers			nomaintainer
 description			Hoe is a way to write Rakefiles much easier and cleaner.
 long_description	Hoe is a simple rake/rubygems helper for project \
@@ -10,9 +10,9 @@ long_description	Hoe is a simple rake/rubygems helper for project \
 					deployment.
 homepage            http://www.zenspider.com/projects/hoe.html
 license				MIT
-checksums			md5 739d4ede50ba5bf9fabb03cef59c3737 \
-					sha1 d858ebf485f98d260a54ba27755d7892b3947641 \
-					rmd160 4610dbe1ffa0f4018248875f4524f9ee0bd5a668
+checksums			rmd160  5daf5370b117934a2de948b10e179d80aa311888 \
+            sha256  01f94e19eeb1ee7c94317a40a3aea7c3aa990cc53df7978e869a15efaa084e27 \
+            size    194048
 platforms           darwin
 
 depends_lib-append  port:rb-rake
diff --git a/ruby/rb-hpricot/Portfile b/ruby/rb-hpricot/Portfile
index 847722af3ba..21af6febc35 100644
--- a/ruby/rb-hpricot/Portfile
+++ b/ruby/rb-hpricot/Portfile
@@ -1,14 +1,14 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			hpricot 0.6.161 gem {} rubygems
+ruby.setup			hpricot 0.8.6 gem {} rubygems
 license				MIT
 maintainers			nomaintainer
 description			a swift, liberal HTML parser with a fantastic library
 long_description	${description}
-checksums			md5 a0c60f8ca593454cbedb04733427604c \
-					sha1 f64fdd6897194ad2af8658d085bccf7a23eb4895 \
-					rmd160 3aff8666bf590630ef477152cdd2a8ce4408642c
+checksums			rmd160  782464d9532ca5008f2e9a1732d9812230069330 \
+            sha256  dfe8f4b3414ba8377d7626030f3aa605caadee9de87cffbeadf8a50359eac8ca \
+            size    293888
 homepage			http://code.whytheluckystiff.net/hpricot/
 platforms           darwin
 
diff --git a/ruby/rb-image_science/Portfile b/ruby/rb-image_science/Portfile
index 587be4e7240..f7479e18c60 100644
--- a/ruby/rb-image_science/Portfile
+++ b/ruby/rb-image_science/Portfile
@@ -1,16 +1,19 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			image_science 1.1.3 gem {} rubygems
+ruby.setup			image_science 1.3.1 gem {} rubygems
 license				MIT
 maintainers			nomaintainer
 description			Ruby library that generates thumbnails
 long_description	${description}
-checksums			md5     b03791c25b4ef5ee0323a23ca15aae09 \
-					sha1    cc6670364f63bd1ee13bb39eaf2f7176c1097c69 \
-					rmd160  b673d11645a90f67bf33cf6c5a54dbc5435d199f
+checksums			rmd160  65de0562681c77ff153cff02957e121ee9c4ff9c \
+            sha256  76d54839540272ad26d0e2ef27cd1de04ea48d537633b1d1c143c0b9b15a66fc \
+            size    20480
 platforms           darwin
 
 depends_run-append  port:freeimage \
 					port:rb-rubyinline \
 					port:rb-hoe
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-hoe \
+                    port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-innate/Portfile b/ruby/rb-innate/Portfile
index 5a227d4ff17..9e506143c4e 100644
--- a/ruby/rb-innate/Portfile
+++ b/ruby/rb-innate/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          innate 2009.10 gem {} rubygems
+ruby.setup          innate 2015.10.28 gem {} rubygems
 
 maintainers         nomaintainer
 categories-append   www devel
@@ -11,8 +11,8 @@ long_description    ${description}
 homepage            https://github.com/manveru/innate
 platforms           darwin
 
-checksums           md5 78e30a90c4126c7a40e8df1159f9616b \
-                    rmd160 f45ff1a5c3789d74e63c46f759916569f47cf787 \
-                    sha1 0e4400f8aaa525eb9558e912c094e950b4da89e0
+checksums           rmd160  7dae2d0b3d7aa8b462296740e2d573f098ae2508 \
+                    sha256  eda8b988bbeeb4a691d0c9529f911755156539220a9643325e36d3bb5a2c463c \
+                    size    108032
 
 depends_lib         port:rb-rack
diff --git a/ruby/rb-json/Portfile b/ruby/rb-json/Portfile
index ce9ce31af52..232f431345a 100644
--- a/ruby/rb-json/Portfile
+++ b/ruby/rb-json/Portfile
@@ -1,8 +1,8 @@
 PortSystem		    1.0
 PortGroup		    ruby 1.0
 
-ruby.setup          json 1.4.6 gem {} rubygems
-revision            1
+ruby.setup          json 2.5.1 gem {} rubygems
+revision            0
 description         JSON implementation as a Ruby extension in C
 long_description    \
     This is a implementation of the JSON specification according to RFC 4627. \
@@ -15,7 +15,10 @@ platforms			darwin
 
 homepage            https://flori.github.io/json/
 
-checksums           md5     10a923c1c031c55d2bac861664431301 \
-                    sha1    a50accee91805a57eb5f4613073edeb422043c57 \
-                    rmd160  bd5736e685d347e774d1a8800f60a8a21f59da2d
+checksums           rmd160  94e457c63cc64b0415927802e31555bdc53a33c4 \
+                    sha256  918d8c41dacb7cfdbe0c7bbd6014a5372f0cf1c454ca150e9f4010fe80cc3153 \
+                    size    89088
 
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-test-unit
diff --git a/ruby/rb-json_pure/Portfile b/ruby/rb-json_pure/Portfile
index ba170039365..b40917c888e 100644
--- a/ruby/rb-json_pure/Portfile
+++ b/ruby/rb-json_pure/Portfile
@@ -1,8 +1,8 @@
 PortSystem		    1.0
 PortGroup		    ruby 1.0
 
-ruby.setup          json_pure 1.4.6 gem {} rubygems
-revision			2
+ruby.setup          json_pure 2.5.1 gem {} rubygems
+revision			0
 description         This is a JSON implementation in pure Ruby.
 long_description    \
     This is a implementation of the JSON specification according to RFC 4627. \
@@ -15,9 +15,9 @@ platforms			darwin
 
 homepage            https://flori.github.io/json/
 
-checksums           md5     efc352b7e48263cba1d4e7d96c7721b1 \
-                    sha1    9fe74cdffaba077e1209f9222e8b7ddd282966df \
-                    rmd160  2ce9c5c4315c330a0f9dac5592e4c8d6c134efc6
+checksums           rmd160  cb2768a49db409f5e21096b6a6f9d0ec598053ea \
+                    sha256  669c0811741f733e3cc0238aa36e9e293dbf360c64cac598c690716404ab100c \
+                    size    61440
 
 # avoid conflict against a command from port:rb-json
 ruby.link_binaries	no
@@ -29,3 +29,6 @@ post-destroot {
 		}
 	}
 }
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-test-unit
diff --git a/ruby/rb-kramdown/Portfile b/ruby/rb-kramdown/Portfile
index 0f8125c0f6b..4a9b2dcb02c 100644
--- a/ruby/rb-kramdown/Portfile
+++ b/ruby/rb-kramdown/Portfile
@@ -3,7 +3,7 @@ PortGroup		ruby 1.0
 PortGroup		github 1.0
 
 ruby.branches   2.7 2.6 2.5 2.4 2.3
-ruby.setup		kramdown 2.3.0 gem
+ruby.setup		kramdown 2.3.1 gem
 revision        0
 maintainers		{kimuraw @kimuraw} openmaintainer
 description		fast, pure-Ruby Markdown-superset converter
@@ -14,8 +14,8 @@ categories-append	textproc
 homepage		https://kramdown.gettalong.org
 license			MIT
 supported_archs	noarch
-checksums		md5 189fc4be1720484335a917be22fa5305 \
-				sha1 63c913ac0a8deb0b1de683684e2971ba03ee69e1 \
-				rmd160 fb9625c56280f6048253ea954887a9c6053def18
+checksums		rmd160  ab4099c7123e9dd32f9c0620278f0d8cb224bf17 \
+           sha256  59e938cfa42a3d6169b295727fe09c4c91d742336c8fbd1042529f4db664ab49 \
+           size    122368
 platforms		darwin
 
diff --git a/ruby/rb-launchy/Portfile b/ruby/rb-launchy/Portfile
index 8478be69005..710d7f4059c 100644
--- a/ruby/rb-launchy/Portfile
+++ b/ruby/rb-launchy/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          launchy 0.3.3 gem {} rubygems
-revision            1
+ruby.setup          launchy 2.5.0 gem {} rubygems
+revision            0
 
 maintainers         nomaintainer
 categories-append   devel
@@ -14,8 +14,15 @@ homepage            https://github.com/copiousfreetime/launchy
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 467abcff90841c06faae6941f0a66910 \
-                    rmd160 a760e0107b5887174e42538bd176e16da4d99c61 \
-                    sha1 b2e4e990d59c89d2a4fabf99a722586966328553
+checksums           rmd160  523d6ff316013c78f5a9b8783fa309d4c8d35331 \
+                    sha256  954243c4255920982ce682f89a42e76372dba94770bf09c23a523e204bdebef5 \
+                    size    30208
 
-depends_lib-append  port:rb-rake port:rb-configuration
+depends_lib-append  port:rb-rake \
+                    port:rb-configuration \
+                    port:rb${ruby.suffix}-addressable
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc \
+                    port:rb${ruby.suffix}-simplecov
diff --git a/ruby/rb-lazylist/Portfile b/ruby/rb-lazylist/Portfile
index e457cdcd5a9..6e6ca9c9bd9 100644
--- a/ruby/rb-lazylist/Portfile
+++ b/ruby/rb-lazylist/Portfile
@@ -1,7 +1,7 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		lazylist 0.2.1 gem {} rubygems
+ruby.setup		lazylist 0.3.2 gem {} rubygems
 license			GPL-2
 maintainers		nomaintainer
 description		        Implementation of lazy lists for ruby
@@ -12,5 +12,9 @@ long_description	    This class implements lazy lists (or streams) for Ruby. Suc
                         calculated on the fly and saved into the list. A value which is \
                         used for a second time is computed only once and just read out \
                         of memory for the second usage.
-checksums		        md5 121b48bde4db3492475e17d19ade02c2
+checksums		        rmd160  787a12b01315255cf10d900f16a457b762efaff2 \
+                   sha256  b0b40f3f5489fec8f236fbb249303962576a15a8415129d1198d8c4a05451974 \
+                   size    28160
 platforms		        darwin
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-dslkit
diff --git a/ruby/rb-lockfile/Portfile b/ruby/rb-lockfile/Portfile
index 859427b899d..42addb12799 100644
--- a/ruby/rb-lockfile/Portfile
+++ b/ruby/rb-lockfile/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          lockfile 1.4.3 gem {} rubygems
-revision            1
+ruby.setup          lockfile 2.1.3 gem {} rubygems
+revision            0
 license             {Ruby GPL-2}
 maintainers         nomaintainer
 description         A ruby library for creating NFS safe lockfiles.
@@ -12,6 +12,6 @@ platforms           darwin
 
 homepage            https://github.com/ahoward/lockfile
 
-checksums           md5     53a63206bbaefb7106db5a74a5adf148 \
-                    sha1    828710234b7ccc87744e9386749b8e2d0657ff41 \
-                    rmd160  fe2ffc3f245b2af75c581038af85e72f79d0cfcf
+checksums           rmd160  fc35efa95a73dd9dc8986d632c5ec3644ae16e0b \
+                    sha256  39cbf399299f140706481370292d941c70e34e98208a78f3739b7aee651c3236 \
+                    size    24064
diff --git a/ruby/rb-madeleine/Portfile b/ruby/rb-madeleine/Portfile
index 3dbab7bca12..aa336477068 100644
--- a/ruby/rb-madeleine/Portfile
+++ b/ruby/rb-madeleine/Portfile
@@ -3,7 +3,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          madeleine 0.7.2 install.rb {README docs contrib samples test} \
+ruby.setup          madeleine 0.9.0 install.rb {README docs contrib samples test} \
                     sourceforge
 categories-append   databases
 platforms           darwin
@@ -19,7 +19,12 @@ long_description    Madeleine is a Ruby  implementation of Object Prevalence, \
                     design is based on Prevayler, the original Java implementation \
                     of object prevalence.
 
-checksums           rmd160  d9c6de2ec03bef3fccccfad4702b67250fdf1374 \
-                    sha256  2c4d79ff859373670536035bec4c2345044b19caeaf7eebfd901a6a2f88acceb
+checksums           rmd160  c8f89b46437305f17c621a389585e1fe4d19c070 \
+                    sha256  12e133bdd79d42a8aa943abbd893f09b150af355cdb84fac08c31bb7c6633f72 \
+                    size    18944
 
 homepage            http://madeleine.sourceforge.net/
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-mime-types/Portfile b/ruby/rb-mime-types/Portfile
index 0c6ae6659f2..9ce9be5b139 100644
--- a/ruby/rb-mime-types/Portfile
+++ b/ruby/rb-mime-types/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			mime-types 1.16 gem {} rubygems
+ruby.setup			mime-types 3.3.1 gem {} rubygems
 license				{Ruby Artistic-1 GPL-2+}
 maintainers			nomaintainer
 description			Manages a MIME Content-Type that will return the \
@@ -10,8 +10,26 @@ long_description	This library allows for the identification of a file's \
 					likely MIME content type. This is release 1.15. The \
 					identification of MIME content type is based on a file's \
 					filename extensions.
-checksums			md5     2c9b8568a76cc632578a292db4a71b9a \
-					sha1    dc9c8d0eca668c18c21302b439645c20327da3ab \
-					rmd160  051bba2db6c6f1690a928f7c7c7364c6e8160912
+checksums			rmd160  19c0ebac4620155e613ffdbb36227970118ff755 \
+            sha256  708f737e28ceef48b9a1bc041aa9eec46fa36eb36acb95e6b64a9889131541fe \
+            size    36352
 platforms			darwin
 homepage			https://github.com/mime-types/ruby-mime-types/
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-mime-types-data
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-fivemat \
+                    port:rb${ruby.suffix}-hoe-doofus \
+                    port:rb${ruby.suffix}-hoe-gemspec2 \
+                    port:rb${ruby.suffix}-hoe-git \
+                    port:rb${ruby.suffix}-hoe-rubygems \
+                    port:rb${ruby.suffix}-hoe-travis \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-minitest-autotest \
+                    port:rb${ruby.suffix}-minitest-bonus-assertions \
+                    port:rb${ruby.suffix}-minitest-focus \
+                    port:rb${ruby.suffix}-minitest-hooks \
+                    port:rb${ruby.suffix}-minitest-rg \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc \
+                    port:rb${ruby.suffix}-simplecov
diff --git a/ruby/rb-mini_portile/Portfile b/ruby/rb-mini_portile/Portfile
index e81b8bd4a67..768b2b2a733 100644
--- a/ruby/rb-mini_portile/Portfile
+++ b/ruby/rb-mini_portile/Portfile
@@ -1,7 +1,7 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		mini_portile 0.5.1 gem {} rubygems
+ruby.setup		mini_portile 0.6.2 gem {} rubygems
 revision		0
 maintainers		{kimuraw @kimuraw} openmaintainer
 description		Simplistic port-like solution for developers
@@ -11,7 +11,6 @@ long_description	Simplistic port-like solution for developers. \
 license			MIT
 platforms		darwin
 homepage		http://nokogiri.org/
-checksums       md5     cb8c0f8e9f3777289613198d0abef699 \
-                sha1    d05bb17e987d7c6a0482a01420ed17d1bf6a3d7f \
-                sha256  efa9058711e1d382b29fd413c728dc2b49c8e6492b558677a17faadf20b54e31 \
-                rmd160  6dd604b506f796a22faf993cc961774511919541
+checksums       rmd160  bd061310e779322f911e7a5569430150894e097d \
+                sha256  5c60cd85db3df6b279e9a6807954c596dc0ced359a10fcd9b49969a6aa8d7d40 \
+                size    13824
diff --git a/ruby/rb-mini_portile2/Portfile b/ruby/rb-mini_portile2/Portfile
index 679da8df353..a44390439f7 100644
--- a/ruby/rb-mini_portile2/Portfile
+++ b/ruby/rb-mini_portile2/Portfile
@@ -2,7 +2,7 @@ PortSystem          1.0
 PortGroup           ruby 1.0
 
 ruby.branches       2.7 2.6 2.5 2.4
-ruby.setup          mini_portile2 2.5.0 gem
+ruby.setup          mini_portile2 2.7.0 gem
 revision            0
 maintainers         nomaintainer
 description         Simplistic port-like solution for developers
@@ -13,6 +13,8 @@ license             MIT
 platforms           darwin
 homepage            https://github.com/flavorjones/mini_portile
 
-checksums           rmd160  36e631c548698ff95011e40442f5ed990d713077 \
-                    sha256  a7a7a09d646619d8efb0898169806266bf2982c70cc131fd285aa25e55bdabc1 \
-                    size    26624
+checksums           rmd160  2988dc25f5311c0540f70a6ce9037ceae57dcef2 \
+                    sha256  6416bf22d3e463fc318b34810920e73055418483b074330d95c773f4596dbdfc \
+                    size    28160
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-webrick
diff --git a/ruby/rb-minitest/Portfile b/ruby/rb-minitest/Portfile
index cd806f5b938..b0c0585d18d 100644
--- a/ruby/rb-minitest/Portfile
+++ b/ruby/rb-minitest/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			minitest 1.7.0 gem {} rubygems
+ruby.setup			minitest 5.14.4 gem {} rubygems
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			minitest/unit is a small and fast replacement for \
 					ruby's huge and slow test/unit
@@ -18,8 +18,10 @@ long_description	minitest/unit is a small and fast replacement for \
 homepage			http://docs.seattlerb.org/minitest/
 license				Ruby
 
-checksums			md5     0bccdbed224b3e027df685598e38a313 \
-					sha1    9d1b572c329758b07dfb58e5daded33b1505d0ab \
-					rmd160  b694fdb1716ab09675e305fc232b5de40a8c22bb
+checksums			rmd160  181570ee707aec0cb7643b4cc2629bb00a2657c5 \
+            sha256  f4716634d71b3ffb627cd63ba4f6f0f77c7a3f17353b1bdf52c8a7f2e0e4e7a7 \
+            size    86016
 platforms			darwin
 
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-mocha/Portfile b/ruby/rb-mocha/Portfile
index 33a7dac98c6..acfe5cc2ffa 100644
--- a/ruby/rb-mocha/Portfile
+++ b/ruby/rb-mocha/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup          mocha 0.9.12 gem {} rubygems
+ruby.setup          mocha 1.13.0 gem {} rubygems
 
 homepage			http://gofreerange.com/mocha/docs
 
@@ -13,6 +13,10 @@ description			Mocha is a library for mocking and stubbing using a syntax like th
 long_description	Mocha is a library for mocking and stubbing using a syntax like that of JMock, and SchMock. \
 					One of its main advantages is that it allows you to mock and stub methods on real (non-mock) \
 					classes and instances.
-checksums			md5 1df8cca1dfc3b15a44ec3c84497cac85 \
-					sha1 9608f143af20514be95ac4385f693f9fe865acb6 \
-					rmd160 e15617c7074d1e7fea24f5344341a805bbbbc3df
+checksums			rmd160  9df3d24830a3fdb34993120f740a511fe0acc369 \
+            sha256  205cfe7b24fe498d6c296abfa798f9b0758fb40984e88dfb4c664eafdf1b4597 \
+            size    68096
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-introspection \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rubocop
diff --git a/ruby/rb-msgpack/Portfile b/ruby/rb-msgpack/Portfile
index 6618c622272..90483cc76fd 100644
--- a/ruby/rb-msgpack/Portfile
+++ b/ruby/rb-msgpack/Portfile
@@ -3,7 +3,7 @@
 PortSystem              1.0
 PortGroup               ruby 1.0
 
-ruby.setup              msgpack 0.4.1 gem {}
+ruby.setup              msgpack 1.4.2 gem {}
 master_sites            http://rubygems.org/gems/msgpack/versions/
 maintainers             nomaintainer
 description             Ruby API for msgpack
@@ -14,6 +14,13 @@ homepage                http://msgpack.sourceforge.net/
 license                 Ruby
 
 master_sites            http://rubygems.org/downloads/
-checksums               md5 f44d4adb4ca7c87b0a562f3d15f3a0e9 \
-                        sha1 5e5ab524198826950593954f29bf8cc48eace753 \
-                        rmd160 492d8a5cc3018ecf798a397e289f4fcdb1ccada7
+checksums               rmd160  f0a9cbe3be2dbcdef58df0468609ef2360a05506 \
+                        sha256  76120b0b135a4a45975b379941068ef594b4ebc3dee6fb22478dea4b74b0b7c0 \
+                        size    57856
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-json \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rake-compiler \
+                    port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-yard
diff --git a/ruby/rb-nanoc/Portfile b/ruby/rb-nanoc/Portfile
index 911a0101ab2..e944c35a549 100644
--- a/ruby/rb-nanoc/Portfile
+++ b/ruby/rb-nanoc/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          nanoc 3.1.3 gem
-revision            1
+ruby.setup          nanoc 4.12.2 gem
+revision            0
 maintainers         nomaintainer
 description         A Ruby site compiler that produces static HTML
 long_description    \
@@ -14,8 +14,18 @@ license             MIT
 platforms           darwin
 homepage            http://nanoc.stoneship.org/
 master_sites        http://rubygems.org/downloads/
-checksums           md5     940c80e92c05e318c0746769fc3969c2 \
-                    sha1    6a31449e1eb8980835ce050ca6d7355cb0025889 \
-                    rmd160  36e5a39da86ece0ed96052f20410b702988c2d9d
+checksums           rmd160  f1350e853f58379b6861d1a6fb109f41036870e1 \
+                    sha256  e884e2432df21cdc33c4ebeae92e9667ba0feb73c2ccfb1af9bdf53d1dfe8a35 \
+                    size    62464
 
 depends_run-append  port:rb-nanoc3
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-addressable \
+                   port:rb${ruby.suffix}-colored \
+                   port:rb${ruby.suffix}-nanoc-checking \
+                   port:rb${ruby.suffix}-nanoc-cli \
+                   port:rb${ruby.suffix}-nanoc-core \
+                   port:rb${ruby.suffix}-nanoc-deploying \
+                   port:rb${ruby.suffix}-parallel \
+                   port:rb${ruby.suffix}-tty-command \
+                   port:rb${ruby.suffix}-tty-which
diff --git a/ruby/rb-nanoc3/Portfile b/ruby/rb-nanoc3/Portfile
index 30f508546fc..ddf6469ff6f 100644
--- a/ruby/rb-nanoc3/Portfile
+++ b/ruby/rb-nanoc3/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          nanoc3 3.1.3 gem
-revision            1
+ruby.setup          nanoc3 3.3.0 gem
+revision            0
 maintainers         nomaintainer
 description         A Ruby site compiler that produces static HTML
 long_description    \
@@ -14,8 +14,10 @@ license             MIT
 platforms           darwin
 homepage            http://nanoc.stoneship.org/
 master_sites        http://rubygems.org/downloads/
-checksums           md5     143f3d8d6c1d3ccd918e40855214a102 \
-                    sha1    db297437d225d5432d79bdfe97337316cbb4ba5b \
-                    rmd160  9354c030c83aff594eb997fd7a6800d651ac2bf8
+checksums           rmd160  0b7d97d603a02c7fcc2e8b9509e4165cfe59843b \
+                    sha256  46f3af105b338d7f4d7f8ec4121320d110385a72cbbc52455226f18bb459dc8d \
+                    size    3584
 
 depends_run-append  port:rb-cri
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-nanoc
diff --git a/ruby/rb-net-scp/Portfile b/ruby/rb-net-scp/Portfile
index 55d486f8dcf..aabc76b05e3 100644
--- a/ruby/rb-net-scp/Portfile
+++ b/ruby/rb-net-scp/Portfile
@@ -1,13 +1,16 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          net-scp 1.0.1 gem {} rubygems
+ruby.setup          net-scp 3.0.0 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         A pure-Ruby implementation of the SCP client protocol
 long_description    ${description}
-checksums           md5     4355d61bccb5cf492d1297701f54eaab \
-                    sha1    84c9a895ad203d496262eb24b8f981482d18cfe1 \
-                    rmd160  96bbe869696f292f886ab003d6ceaa0d2fcf90af
+checksums           rmd160  bede44dfc9e99c504b7dcd61e52b580f7e971ab8 \
+                    sha256  8fc6c80365b95230c6bfc529dbea3893d2d81724855bfb01cbf385866e1c902c \
+                    size    31744
 platforms           darwin
 homepage            https://github.com/net-ssh/net-scp
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-mocha \
+                    port:rb${ruby.suffix}-test-unit
diff --git a/ruby/rb-net-sftp/Portfile b/ruby/rb-net-sftp/Portfile
index 78f7ee73d19..14d32e83576 100644
--- a/ruby/rb-net-sftp/Portfile
+++ b/ruby/rb-net-sftp/Portfile
@@ -1,13 +1,16 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          net-sftp 2.0.2 gem {} rubygems
+ruby.setup          net-sftp 3.0.0 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         A pure Ruby implementation of the SFTP client protocol
 long_description    ${description}
-checksums           md5     1153ab84a10a17f6eec187e456fab71c \
-                    sha1    e38d1c9b3697d9854c24fcdc3cf7bad6a3e5f7c4 \
-                    rmd160  20ba6be49d08e212b3c00f0c7105e317f96ea3ac
+checksums           rmd160  8ee58a19b081007027aa577af474350b1207f082 \
+                    sha256  b1a2d6cd0bfe8b38f2c199614b86591455f582dbdd6211c95af861fb97d7bba0 \
+                    size    54784
 platforms           darwin
 homepage            https://github.com/net-ssh/net-sftp
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-mocha
diff --git a/ruby/rb-net-ssh-gateway/Portfile b/ruby/rb-net-ssh-gateway/Portfile
index 15f134bd28d..53341fefaaa 100644
--- a/ruby/rb-net-ssh-gateway/Portfile
+++ b/ruby/rb-net-ssh-gateway/Portfile
@@ -1,13 +1,18 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          net-ssh-gateway 1.0.1 gem {} rubygems
+ruby.setup          net-ssh-gateway 2.0.0 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         A simple library to assist in establishing tunneled Net::SSH connection
 long_description    ${description}
-checksums           md5     7b2a6e3b250c23872b4179f2ddc941af \
-                    sha1    d45f7e0d26fc37cecc77243760b8e1a4d165d93b \
-                    rmd160  dce96b5eff1b94d44fb3f4b6594fff0c3540ae50
+checksums           rmd160  6f78d46e5dc711441970ceda0ed27d97a02df29f \
+                    sha256  1d9cb51de52e2d64982f4c136c30435e914c05a980814a91055c89e183397bd0 \
+                    size    14848
 platforms           darwin
 homepage            https://github.com/net-ssh/net-ssh-gateway
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-mocha \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-net-ssh/Portfile b/ruby/rb-net-ssh/Portfile
index 0634f11c4c1..1413f753136 100644
--- a/ruby/rb-net-ssh/Portfile
+++ b/ruby/rb-net-ssh/Portfile
@@ -1,13 +1,22 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          net-ssh 2.0.14 gem {} rubygems
+ruby.setup          net-ssh 6.1.0 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         A pure-Ruby implementation of the SSH2 client protocol
 long_description    ${description}
-checksums           md5     ef2e16b0cbe1ee09b1e4118905c992f4 \
-                    sha1    05aad2cd0af4ecaa009fa7d94ed22ab8d99277f7 \
-                    rmd160  e6044ef9115558b49605d09e6e498aeb4a26c1d7
+checksums           rmd160  5c9c97750b7b1860b748698b23796ee4d70b380a \
+                    sha256  8905c1f9209fb216c59cc631c2e4085b1a9660598da6de0f20323264d993e34a \
+                    size    134656
 platforms           darwin
 homepage            http://net-ssh.github.io/net-ssh/
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bcrypt_pbkdf \
+                    port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-ed25519 \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-mocha \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rubocop \
+                    port:rb${ruby.suffix}-x25519
diff --git a/ruby/rb-net-yail/Portfile b/ruby/rb-net-yail/Portfile
index 2826a4a5ef3..f4c50c40162 100644
--- a/ruby/rb-net-yail/Portfile
+++ b/ruby/rb-net-yail/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          net-yail 1.3.2 gem {} rubygems
+ruby.setup          net-yail 1.6.2 gem {} rubygems
 categories-append   irc net
 license             MIT
 maintainers         nomaintainer
@@ -12,6 +12,6 @@ long_description \
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 4db4b5cee2cb6c7dbb142cc979080c7d \
-                    sha1 214e0fb58805a5f359dad9fef5c6648f0413288b \
-                    rmd160 9a5dac1bba9bf6caa7a363a53227d2a20613c1de
+checksums           rmd160  89148a60840c91e4ae7cd35aac7b1a5fc279c9c4 \
+                    sha256  1901f8e036b6aa3d3b0ccfa06e97904046ede6bc93e694434a76a88b1f9f39a3 \
+                    size    44032
diff --git a/ruby/rb-netaddr/Portfile b/ruby/rb-netaddr/Portfile
index c5a10b2440a..bdbaf2f5a59 100644
--- a/ruby/rb-netaddr/Portfile
+++ b/ruby/rb-netaddr/Portfile
@@ -3,7 +3,7 @@
 PortSystem              1.0
 PortGroup               ruby 1.0
 
-ruby.setup              netaddr 1.5.0 gem {} rubygems
+ruby.setup              netaddr 2.0.4 gem {} rubygems
 categories-append       net
 license                 {Ruby GPL-2}
 platforms               darwin
@@ -15,6 +15,6 @@ long_description        \
     create CIDR-based hierarchical trees, manipulate MAC addresses, and \
     much more.
 
-checksums               md5     484de4eb10ab991e5c9f1fff1df13b5d \
-                        sha1    d8c11f3509273ed62e497e84099fd6069b64fccb \
-                        rmd160  0edc1cb72b82e627633fbcd3f91f6ee90be8a04e
+checksums               rmd160  cea747fb584844e94a75f4b513f0f09ddd318146 \
+                        sha256  57d76b012075c7189b14eb7bfe8ac110f59979abb6d0244dc6791ce621d873aa \
+                        size    22016
diff --git a/ruby/rb-nokogiri/Portfile b/ruby/rb-nokogiri/Portfile
index cf139a13f5e..d19a43a74db 100644
--- a/ruby/rb-nokogiri/Portfile
+++ b/ruby/rb-nokogiri/Portfile
@@ -4,7 +4,7 @@ PortSystem          1.0
 PortGroup           ruby 1.0
 
 ruby.branches       2.7 2.6 2.5 2.4
-ruby.setup          nokogiri 1.11.1 gem
+ruby.setup          nokogiri 1.12.4 gem
 revision            0
 maintainers         {kimuraw @kimuraw} openmaintainer
 description         Nokogiri is an HTML, XML, SAX, and Reader parser.
@@ -15,9 +15,9 @@ license             MIT
 platforms           darwin
 homepage            http://nokogiri.org/
 
-checksums           rmd160  2eaf4bdad13c344d7cfe6f67366bbdcd42cd8a11 \
-                    sha256  42c2a54dd3ef03ef2543177bee3b5308313214e99f0d1aa85f984324329e5caa \
-                    size    9266176
+checksums           rmd160  cc3550259ed66d0a2871622c102050eca6d497c2 \
+                    sha256  7fec161ee1c7b2329e05fed019bfc7b1f910a39e6b30ae95825e75dda2094de9 \
+                    size    9588736
 
 if {${name} ne ${subport}} {
     depends_extract     port:rb${ruby.suffix}-gem-patch
diff --git a/ruby/rb-og/Portfile b/ruby/rb-og/Portfile
index e60ab8617cd..650336f3561 100644
--- a/ruby/rb-og/Portfile
+++ b/ruby/rb-og/Portfile
@@ -1,8 +1,8 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		og 0.9.5 gem {} rubygems
-revision        1
+ruby.setup		og 0.41.0 gem {} rubygems
+revision        0
 maintainers		nomaintainer
 description		    Og provides transparent serialization of object graphs to \
                     a RDBMS backend
@@ -17,5 +17,9 @@ long_description	Unlike other similar libraries Og maps standard Ruby \
                     Entities.
 categories-append   databases
 license				BSD
-checksums		    md5 158e4304d88213d5ae43d39bd2c895e6
+checksums		    rmd160  dbd9107ee99b1fd578a81a057bb2b56b29839564 \
+               sha256  0f0ec20d17c5246fb56a8c3f2e4170b777c5b50ea0d2c9d8fcb267a2bde6a163 \
+               size    109568
 platforms		    darwin
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-glue
diff --git a/ruby/rb-pkg-config/Portfile b/ruby/rb-pkg-config/Portfile
index 4139c226d0c..30b0c0809b2 100644
--- a/ruby/rb-pkg-config/Portfile
+++ b/ruby/rb-pkg-config/Portfile
@@ -3,8 +3,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          pkg-config 1.1.4 gem {} rubygems
-revision            2
+ruby.setup          pkg-config 1.4.6 gem {} rubygems
+revision            0
 description         A pkg-config implmenetation by Ruby
 long_description    A pkg-config implmenetation by Ruby
 maintainers         {kimuraw @kimuraw} openmaintainer
@@ -13,7 +13,6 @@ homepage            https://github.com/rcairo/pkg-config
 license             LGPL-2+
 supported_archs     noarch
 
-checksums           md5     cae3d681a928482108b670ceda8c3eec \
-                    sha1    20266e013b094e539bbb218daad8235ef987d7c9 \
-                    sha256  c08fc6596eeef6f0fcfd4c8433010a143c22142f9cccbc2666f32c67c5af8b34 \
-                    rmd160  d9c35bf1e7015db96e01e9d8b1f3736a47047468
+checksums           rmd160  25837d0e16a233bbffb1f7c095cef363f05dd887 \
+                    sha256  54be9117d55d9eba2ca5eb990548b539afc958be5b77e7a6fdc4e49e5ff052d6 \
+                    size    22528
diff --git a/ruby/rb-polyglot/Portfile b/ruby/rb-polyglot/Portfile
index 11391b35a91..572aa3ca3ea 100644
--- a/ruby/rb-polyglot/Portfile
+++ b/ruby/rb-polyglot/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          polyglot 0.2.9 gem {} rubygems
+ruby.setup          polyglot 0.3.5 gem {} rubygems
 
 maintainers         nomaintainer
 description         Allows custom language loaders for file extensions to be hooked into require
@@ -13,6 +13,6 @@ supported_archs     noarch
 
 depends_lib-append  port:rb-hoe
 
-checksums           md5 b3429c0f849dcaf63e443357afc342b6 \
-                    rmd160 df62129dac19d72162972f92a1dedba404f829d1 \
-                    sha1 2848efd9ebb61477d55c16d9ea25298bbd3e5f8f
+checksums           rmd160  8f5260ffec2774621d474a40824ae24bc806112e \
+                    sha256  59d66ef5e3c166431c39cb8b7c1d02af419051352f27912f6a43981b3def16af \
+                    size    8192
diff --git a/ruby/rb-postgres/Portfile b/ruby/rb-postgres/Portfile
index 105006c9179..8e654fe2cf7 100644
--- a/ruby/rb-postgres/Portfile
+++ b/ruby/rb-postgres/Portfile
@@ -1,8 +1,8 @@
 PortSystem 1.0
 PortGroup ruby 1.0
 
-ruby.setup		{postgres ruby-postgres} 0.7.1 extconf.rb {README doc sample}
-revision		5
+ruby.setup		{postgres ruby-postgres} 0.8.1 extconf.rb {README doc sample}
+revision		0
 maintainers		nomaintainer
 description		Ruby API for the PostgreSQL database
 long_description	This is the Ruby library for accessing PostgreSQL \
@@ -11,7 +11,9 @@ categories-append	databases
 license			{Ruby GPL-2}
 homepage		http://ruby.scripting.ca/postgres/
 master_sites	${homepage}/archive/
-checksums		md5 8ef67b3f4b089248f0420baeb0e3b3c8
+checksums		rmd160  c040d6ca0c7a7cf2e3ad74b80b47536d9d2b0fa5 \
+           sha256  17985ae5b7bf134df1039a8a2edad05abb93acbc9822419d0e70e9efd103c911 \
+           size    7680
 platforms		darwin
 
 if {![variant_isset postgresql83] && ![variant_isset postgresql82] &&
@@ -21,7 +23,8 @@ if {![variant_isset postgresql83] && ![variant_isset postgresql82] &&
 
 variant postgresql83 conflicts postgresql80 postgresql81 postgresql82 \
 			description {Use PostgreSQL version 8.3} {
-	depends_lib-append	port:postgresql83
+	depends_lib-append	port:postgresql83 \
+	                  	port:rb${ruby.suffix}-pg
 	configure.args-append	--with-pgsql-include-dir=${prefix}/include/postgresql83 \
 				--with-pgsql-lib-dir=${prefix}/lib/postgresql83
 	configure.env \
@@ -58,3 +61,8 @@ variant postgresql80 conflicts postgresql81 postgresql82 postgresql83 \
 		"POSTGRES_LIB=${prefix}/lib/postgresql80 -L${prefix}/lib -lssl -lcrypto" \
 		"POSTGRES_INCLUDE=${prefix}/include/postgresql80 -I${prefix}/include"
 }
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-hoe \
+                    port:rb${ruby.suffix}-hoe-highline \
+                    port:rb${ruby.suffix}-hoe-mercurial \
+                    port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-rack/Portfile b/ruby/rb-rack/Portfile
index 2919de7bf27..83ea276f504 100644
--- a/ruby/rb-rack/Portfile
+++ b/ruby/rb-rack/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rack 1.0.1 gem {} rubygems
-revision            1
+ruby.setup          rack 2.2.3 gem {} rubygems
+revision            0
 
 maintainers         nomaintainer
 categories-append   www devel
@@ -14,6 +14,11 @@ platforms           darwin
 
 homepage            https://rack.github.io
 
-checksums           md5 22268803c9b8b785ed30fcee5bce3ce7 \
-                    rmd160 8b4448492f2fb2288df7249cb9e96f57f71ac75f \
-                    sha1 49ae682c029daa5007e7fe7f47096c8788743c8e
+checksums           rmd160  bd8c4bdbaf5a160c10d03113ba6b3137f709c810 \
+                    sha256  2638e7eb6689a5725c7e16f30cc4aa4e31694dc3ca30d790952526781bd0bb44 \
+                    size    151040
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-minitest-global_expectations \
+                    port:rb${ruby.suffix}-minitest-sprint \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-rails/Portfile b/ruby/rb-rails/Portfile
index bc3190c4f34..a632935e0a6 100644
--- a/ruby/rb-rails/Portfile
+++ b/ruby/rb-rails/Portfile
@@ -1,8 +1,8 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        rails 2.3.5 gem {} rubygems
-revision          1
+ruby.setup        rails 6.1.4.1 gem {} rubygems
+revision          0
 categories-append www devel
 maintainers       nomaintainer
 description       Ruby web-application framework for the MVC pattern.
@@ -11,9 +11,9 @@ long_description  Rails is a web-application framework for the MVC pattern \
                   framework, and object-relational mapping package. \
                   Everything needed to develop web-apps that can run \
                   on CGI, FastCGI, and mod_ruby.
-checksums           md5     d09038cee224b1a51ae50eff772cd8f2 \
-                    sha1    e341aba6d1be9ec89ffe924a960e2c56c073954c \
-                    rmd160  6807ad6bbf04949e0f866ce05da0b321600572ea
+checksums           rmd160  640f1e0e60e63c3f953e3f8b0ad1a24bda8e0ef8 \
+                    sha256  7f5dd7a71046aedb6859eb4288b31b738fb8544bd9fb27574085b58cbaa8a9f8 \
+                    size    6656
 platforms         darwin
 
 depends_lib-append  port:rb-rake \
@@ -22,4 +22,14 @@ depends_lib-append  port:rb-rake \
                     port:rb-actionpack \
                     port:rb-actionmailer \
                     port:rb-activeresource \
-                    port:rb-sqlite3
+                    port:rb-sqlite3 \
+                    port:rb${ruby.suffix}-actioncable \
+                    port:rb${ruby.suffix}-actionmailbox \
+                    port:rb${ruby.suffix}-actiontext \
+                    port:rb${ruby.suffix}-actionview \
+                    port:rb${ruby.suffix}-activejob \
+                    port:rb${ruby.suffix}-activemodel \
+                    port:rb${ruby.suffix}-activestorage \
+                    port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-railties \
+                    port:rb${ruby.suffix}-sprockets-rails
diff --git a/ruby/rb-rake/Portfile b/ruby/rb-rake/Portfile
index 5a598351850..3bfdfe304f2 100644
--- a/ruby/rb-rake/Portfile
+++ b/ruby/rb-rake/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
-ruby.setup          rake 0.8.7 gem {} rubygems
-revision            2
+ruby.setup          rake 13.0.6 gem {} rubygems
+revision            0
 categories-append   devel
 license             MIT
 platforms           darwin
@@ -21,8 +21,8 @@ long_description    This package contains Rake, a simple ruby build \
                     other projects as a single file.  Projects that \
                     depend upon rake do not require that rake be \
                     installed on target systems.
-checksums           md5     d9eb83525310ad1a0e8a3eeddfe3c65f \
-                    sha1    91daad079d404b68a7dd179716b9fdd0c195144c \
-                    rmd160  1c41208b3bf8fba5a89a7b156eb862c4cf6278f0
+checksums           rmd160  fbb9176ae67b3fcf3874dc4c3f4518e1e01d7c07 \
+                    sha256  5ce4bf5037b4196c24ac62834d8db1ce175470391026bd9e557d669beeb19097 \
+                    size    84992
 
 universal_variant   no
diff --git a/ruby/rb-ramaze/Portfile b/ruby/rb-ramaze/Portfile
index 5cbf9572267..802d554c8b5 100644
--- a/ruby/rb-ramaze/Portfile
+++ b/ruby/rb-ramaze/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          ramaze 2009.10 gem {} rubygems
+ruby.setup          ramaze 2012.12.08 gem {} rubygems
 
 maintainers         nomaintainer
 categories-append   www devel
@@ -12,8 +12,21 @@ long_description    Ramaze is a simple, light and modular open-source \
 homepage            http://ramaze.net/
 platforms           darwin
 
-checksums           md5 e97055aa3b8ce4e744dc71fba36368d4 \
-                    rmd160 63858ae528f8493dbc83d2d10fe283b06f857fe7 \
-                    sha1 79b72bb8f37e21ece0847169397ad9619ebbab61
+checksums           rmd160  2c839183a1675261d10a0ef7c05b0cca2ba3c831 \
+                    sha256  a9b91becc26d1249ec667b2b08186883e21e3722b9ad5ffc9d95cef1ec23ab35 \
+                    size    513536
 
 depends_lib         port:rb-innate
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-rake
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-dalli \
+                    port:rb${ruby.suffix}-lokar \
+                    port:rb${ruby.suffix}-mustache \
+                    port:rb${ruby.suffix}-nokogiri \
+                    port:rb${ruby.suffix}-rdiscount \
+                    port:rb${ruby.suffix}-redis \
+                    port:rb${ruby.suffix}-sass \
+                    port:rb${ruby.suffix}-slim \
+                    port:rb${ruby.suffix}-sqlite3 \
+                    port:rb${ruby.suffix}-yard
diff --git a/ruby/rb-rbot/Portfile b/ruby/rb-rbot/Portfile
index 96dcd023a36..7aa2f45201b 100644
--- a/ruby/rb-rbot/Portfile
+++ b/ruby/rb-rbot/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rbot 0.9.14 gem
-revision            1
+ruby.setup          rbot 0.9.15 gem
+revision            0
 
 categories-append   irc
 license             {MIT GPL-2}
@@ -19,9 +19,9 @@ supported_archs     noarch
 homepage            http://ruby-rbot.org/
 master_sites        ${homepage}download/
 
-checksums           md5 9ff6fc4afcc62f3a264d5ccf4df3c9ff \
-                    sha1 c4dd6b83bbc67aa040bdcefe2f6422b74995cfe5 \
-                    rmd160 b551796d6187bc6b97136e93b76e9b14200e9046
+checksums           rmd160  aadd199161edf2765846a3c0cd85caf92421d1d6 \
+                    sha256  b7874a05d4bee704cd28d903d628d3e5e9b2fcc8fe13c8c4abeac9f4c9ae7912 \
+                    size    713216
 
 depends_run         port:rb-bdb
 
diff --git a/ruby/rb-rcov/Portfile b/ruby/rb-rcov/Portfile
index 796a6a06549..b023bca3d36 100644
--- a/ruby/rb-rcov/Portfile
+++ b/ruby/rb-rcov/Portfile
@@ -3,8 +3,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rcov 0.8.1.2.0 gem {} rubygems
-revision            1
+ruby.setup          rcov 1.0.0 gem {} rubygems
+revision            0
 license             Ruby BSD
 maintainers         nomaintainer
 description         Coverage tool for Ruby
@@ -16,7 +16,7 @@ long_description    rcov is (mainly) a code coverage tool for Ruby featuring \
 
 homepage            https://github.com/relevance/rcov
 
-checksums           md5     89f80418847e5ceef89478b09b36b110 \
-                    sha1    5f922dcfbceeb02fc3cf615946e68c34ac63cd79 \
-                    rmd160  f477239223e3d5dc98054a766a69553f88d7b037
+checksums           rmd160  ba26544e3c422b632781c3ab6ac781a488371b30 \
+                    sha256  929cbdd693cd6e9b28458bf075591f8045c55a9e2e71693707161ee87b4f17e0 \
+                    size    59392
 platforms           darwin
diff --git a/ruby/rb-rdtool/Portfile b/ruby/rb-rdtool/Portfile
index df9dcd25244..2760e7553ff 100644
--- a/ruby/rb-rdtool/Portfile
+++ b/ruby/rb-rdtool/Portfile
@@ -2,7 +2,7 @@ PortSystem		1.0
 PortGroup		ruby 1.0
 PortGroup		github 1.0
 
-version			0.6.37
+version			0.6.38
 github.setup	uwabami rdtool ${version} v
 ruby.setup		rdtool ${version} setup.rb {README.rd README.rd.ja doc utils}
 maintainers		{kimuraw @kimuraw}
@@ -15,9 +15,9 @@ categories-append	textproc
 license			{Ruby GPL}
 platforms		darwin
 supported_archs	noarch
-checksums		md5 69dab7c77d62f51ca11e5d1f201c9f84 \
-				rmd160 be9644258c07a1d694a37b3a53636e0cef951430 \
-				sha1 77fad4202113d829f98639572ec85bb51701af6f
+checksums		rmd160  5b4efcaefb504f1c82a052c69d7d7434358aa818 \
+           sha256  d9d32e215c1958847001ca5940ad42aa8bcbdf984436f1235b9dbd300e4c74bc \
+           size    115712
 
 test.run		yes
 test.cmd		${ruby.bin} -I./lib ./test.rb
diff --git a/ruby/rb-rest-client/Portfile b/ruby/rb-rest-client/Portfile
index 13b6da0b3e2..9594ca6ca06 100644
--- a/ruby/rb-rest-client/Portfile
+++ b/ruby/rb-rest-client/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rest-client 1.0.3 gem {} rubygems
-revision            1
+ruby.setup          rest-client 2.1.0 gem {} rubygems
+revision            0
 
 maintainers         nomaintainer
 categories-append   www devel
@@ -14,6 +14,19 @@ homepage            http://rest-client.heroku.com/
 platforms           darwin
 supported_archs     noarch
 
-checksums           md5 fe2e80acbff7c701d8eb5f64e57e14b4 \
-                    rmd160 29a88af0179c73a5359714f391ef609e5d686da3 \
-                    sha1 1deb86bc1ae426be553abb27922cb9082013ea1a
+checksums           rmd160  6b5fbbaaac81d4a346cb977c49db8bfca0c7d4b7 \
+                    sha256  a35a3bb8d16ca39d110a946a2c805267f98ce07a0ae890e4512a45eadea47a6e \
+                    size    147456
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-ffi \
+                   port:rb${ruby.suffix}-http-accept \
+                   port:rb${ruby.suffix}-http-cookie \
+                   port:rb${ruby.suffix}-mime-types \
+                   port:rb${ruby.suffix}-netrc
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-pry \
+                    port:rb${ruby.suffix}-pry-doc \
+                    port:rb${ruby.suffix}-rdoc \
+                    port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-rubocop \
+                    port:rb${ruby.suffix}-webmock
diff --git a/ruby/rb-rgl/Portfile b/ruby/rb-rgl/Portfile
index cf42c81dbdf..1b2caddc5d3 100644
--- a/ruby/rb-rgl/Portfile
+++ b/ruby/rb-rgl/Portfile
@@ -1,12 +1,19 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		    rgl 0.4.0 gem {} rubygems
+ruby.setup		    rgl 0.5.7 gem {} rubygems
 license		        {Ruby GPL-2}
 maintainers		    nomaintainer
 description		    RGL Ruby Graph Library
 long_description	A framework for graph data structures and algorithms
-checksums		    md5 a3711ebdab146e16f42136a39062c16e
+checksums		    rmd160  ab4492d5589068aff33a70c56c6daec73f13ebe2 \
+               sha256  b0a0caddb1e12e10f3c4178a7543c8b504cd7e8ca615bb6c580e40ad18adc62f \
+               size    65024
 homepage            https://github.com/monora/rgl
 platforms		    darwin
-depends_lib-append  port:rb-stream
+depends_lib-append  port:rb-stream \
+                    port:rb${ruby.suffix}-lazy_priority_queue
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-test-unit \
+                    port:rb${ruby.suffix}-yard
diff --git a/ruby/rb-rio/Portfile b/ruby/rb-rio/Portfile
index 0d0806e18cb..2f4d93852a5 100644
--- a/ruby/rb-rio/Portfile
+++ b/ruby/rb-rio/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			rio 0.4.1 gem {} rubygems
+ruby.setup			rio 0.6.0 gem {} rubygems
 license				GPL-2+
 maintainers			nomaintainer
 description			Rio - Ruby I/O Facilitator
@@ -12,8 +12,8 @@ long_description	Rio is a facade for most of the standard ruby classes that \
 					others. Rio also provides an application level interface \
 					which allows many common I/O idioms to be expressed \
 					succinctly.
-checksums			md5     0af95d12c0e0f04cc8b81668c51c0148 \
-					sha1    ac5555988594a5e30ad77641875a73b5e8bc4167 \
-					rmd160  9659ba33f292b5029f39c7ae398d5108034d54dd
+checksums			rmd160  a61ce80786796ab518c40b46acb88feb78c35411 \
+            sha256  5b09f723f2ac48c5e0ab6085e7f2bb0e74626d0e6e44e3775d7fe7c1aa6055a3 \
+            size    216064
 homepage			http://rio4ruby.com/
 platforms           darwin
diff --git a/ruby/rb-rmail/Portfile b/ruby/rb-rmail/Portfile
index fa65f47ecf2..a84a79b47dc 100644
--- a/ruby/rb-rmail/Portfile
+++ b/ruby/rb-rmail/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rmail 1.0.0 gem {} rubygems
+ruby.setup          rmail 1.1.4 gem {} rubygems
 categories-append   mail
 license             BSD
 maintainers         nomaintainer
@@ -15,9 +15,9 @@ platforms           darwin
 
 homepage            http://www.rfc20.org/rubymail/
 
-checksums           md5     c94a6595a71aec61da5723699caea38c \
-                    sha1    0c946e2e7daf5468a338ce42177f52bd4f89eb82 \
-                    rmd160  9a6069172ac6bed7355c0f4b4325ec8cea4582bc
+checksums           rmd160  e83fe5090608bf7c69f791c840cbebc76f7da43c \
+                    sha256  11338a9834b207a6989826bb3d9c5505a339dcd3eacbcf8b389598b3ebbcb654 \
+                    size    75264
 
 test.run            yes
 test.cmd            ${ruby.bin} tests/runtests.rb
diff --git a/ruby/rb-roauth/Portfile b/ruby/rb-roauth/Portfile
index 6af2847d50e..eebb0452ef7 100644
--- a/ruby/rb-roauth/Portfile
+++ b/ruby/rb-roauth/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			roauth 0.0.2 gem {} rubygems
+ruby.setup			roauth 0.0.8 gem {} rubygems
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			Simple Ruby OAuth library
 long_description	A simple OAuth library that supports OAuth header \
@@ -10,8 +10,8 @@ long_description	A simple OAuth library that supports OAuth header \
 homepage			https://github.com/maccman/roauth
 license				Ruby
 
-checksums			md5     7fb6b23065027e057e2a91c4ded396db \
-					sha1    8eba505cb817564e162dc33ea132a32b908d5c05 \
-					rmd160  4e582acaf9d34f3d43ab0985c18b88d91ad584b0
+checksums			rmd160  040960697f278b1598f04b3941f2ad72f90038fc \
+            sha256  4142852a18e60ba203fa9a954dda8b4c7465f6662eae96f7a109f056e6715fe7 \
+            size    7168
 platforms			darwin
 
diff --git a/ruby/rb-rspec-rails/Portfile b/ruby/rb-rspec-rails/Portfile
index fe25af2c13d..56606f1297a 100644
--- a/ruby/rb-rspec-rails/Portfile
+++ b/ruby/rb-rspec-rails/Portfile
@@ -1,15 +1,27 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rspec-rails 1.1.11 gem {} rubygems
+ruby.setup          rspec-rails 5.0.2 gem {} rubygems
 license             MIT
 maintainers         nomaintainer
 description         Behaviour Driven Development framework for Ruby on Rails
 long_description    ${description}
-checksums           md5     bc05660e777c5222b9902c7c3873759d \
-                    sha1    37c7552a09b23d1aca13278568bbe97b5c2f7abc \
-                    rmd160  b04e39fdb4c6023c4488ed138f5043ec6353ef30
+checksums           rmd160  31e82eede6215059fe5747b68e80f16b7237d041 \
+                    sha256  c99e6d41895bb810ec9e74362b9dc67b3799032a1f69d8bb2df1a35b80f85e94 \
+                    size    69120
 platforms           darwin
 homepage            http://rspec.info/
 depends_run         port:rb-rspec \
                     port:rb-rails
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-actionpack \
+                   port:rb${ruby.suffix}-activesupport \
+                   port:rb${ruby.suffix}-railties \
+                   port:rb${ruby.suffix}-rspec-core \
+                   port:rb${ruby.suffix}-rspec-expectations \
+                   port:rb${ruby.suffix}-rspec-mocks \
+                   port:rb${ruby.suffix}-rspec-support
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-ammeter \
+                    port:rb${ruby.suffix}-aruba \
+                    port:rb${ruby.suffix}-cucumber
diff --git a/ruby/rb-rspec/Portfile b/ruby/rb-rspec/Portfile
index cb688d1b8f4..2ef6d4cdec0 100644
--- a/ruby/rb-rspec/Portfile
+++ b/ruby/rb-rspec/Portfile
@@ -1,14 +1,18 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          rspec 1.1.11 gem {} rubygems
-revision            1
+ruby.setup          rspec 3.10.0 gem {} rubygems
+revision            0
 license             MIT
 maintainers         nomaintainer
 description         Behaviour Driven Development framework for Ruby
 long_description    ${description}
-checksums           md5     04d59c2b715fe97a5763d7abf322afbb \
-                    sha1    075fa05b9f864a1a081632445827f287102a8534 \
-                    rmd160  40ec791e226c9b50f733983cfd19774feac7ab5f
+checksums           rmd160  af288fdc47f92dd04b71b0e59b0a044c540125f9 \
+                    sha256  b870b43d49ae4a4e063b94976d2742b0854ec10458c425d569b5556ee5898ab7 \
+                    size    10752
 platforms           darwin
 homepage            http://rspec.info/
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-rspec-core \
+                   port:rb${ruby.suffix}-rspec-expectations \
+                   port:rb${ruby.suffix}-rspec-mocks
diff --git a/ruby/rb-ruby-debug-base/Portfile b/ruby/rb-ruby-debug-base/Portfile
index 3aeacb349a2..062c6403bc6 100644
--- a/ruby/rb-ruby-debug-base/Portfile
+++ b/ruby/rb-ruby-debug-base/Portfile
@@ -3,7 +3,7 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        ruby-debug-base 0.9.3 gem {} rubygems
+ruby.setup        ruby-debug-base 0.10.4 gem {} rubygems
 
 platforms         darwin
 categories-append devel
@@ -17,6 +17,6 @@ long_description  Ruby debugger core API written in C. Use this if you want to \
                   somewhat stable.
 homepage          https://github.com/ruby-debug/
 
-checksums         md5 9ba1ffabdf823225397834f3b64b83d5 \
-                  sha1 96138d1287846f4ae23515de304f386f79c953c8 \
-                  rmd160 ef1e4da6b3474fd1e883c90e72b3afe3ec6bf0c9
+checksums         rmd160  6a0e4cfeb9ce0d4ed208e2a004874bea51c6400d \
+                  sha256  83d15c1d0f1795f8f2c02869815d558840d62c69855a599606aba4f6c879207c \
+                  size    61440
diff --git a/ruby/rb-ruby-debug/Portfile b/ruby/rb-ruby-debug/Portfile
index 438eacba856..7ee8bcacffc 100644
--- a/ruby/rb-ruby-debug/Portfile
+++ b/ruby/rb-ruby-debug/Portfile
@@ -3,19 +3,21 @@
 PortSystem        1.0
 PortGroup         ruby 1.0
 
-ruby.setup        ruby-debug 0.9.3 gem {} rubygems
+ruby.setup        ruby-debug 0.11.0 gem {} rubygems
 
 platforms         darwin
 categories-append devel
 maintainers       {internode.on.net:arsptr @randomphrase}
 
-depends_lib-append port:rb-ruby-debug-base
+depends_lib-append port:rb-ruby-debug-base \
+                   port:rb${ruby.suffix}-columnize \
+                   port:rb${ruby.suffix}-linecache
 
 description       Ruby CLI debugger
 
 long_description  ${description}
 homepage          https://github.com/ruby-debug/
 
-checksums         md5 e93d80dc013b1154ff5da2c0e371308e \
-                  sha1 9d63c8a8527741194c49597d2bfc8fb8cd752261 \
-                  rmd160 028872a1263a8bdfacb2f54d303a063548011e98
+checksums         rmd160  00b008c2cf6f41cc1e99c44b742552613995dd07 \
+                  sha256  839adca0b029dc956a7327385f6820a03c49b0b77c892a711841af691d082a3c \
+                  size    53248
diff --git a/ruby/rb-ruby-openid/Portfile b/ruby/rb-ruby-openid/Portfile
index 803be81ed8b..cb7f65441d2 100644
--- a/ruby/rb-ruby-openid/Portfile
+++ b/ruby/rb-ruby-openid/Portfile
@@ -1,12 +1,14 @@
 PortSystem 1.0
 PortGroup			ruby 1.0
 
-ruby.setup			ruby-openid 2.1.2 gem {} rubygems
+ruby.setup			ruby-openid 2.9.2 gem {} rubygems
 license				Apache-2 Ruby
 maintainers			nomaintainer
 description			A robust library for verifying and serving OpenID identities.
 long_description	${description}
-checksums			md5 a5c07fc20784e01d35e9ce13451ae19a \
-					sha1 241bd1dfa02119c029a871dd3d9c7c8ab24d32ca \
-					rmd160 6b75b60792c5c90e57e5b262d563c332441eddf4
+checksums			rmd160  47ce2d2d0bcbb842300ecd891c4cb58d0365f3f9 \
+            sha256  7f8e39426b9833172a79f4696bc63b66b0d2c766971919a69b3db5be400d17a4 \
+            size    331776
 platforms           darwin
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-minitest
diff --git a/ruby/rb-runt/Portfile b/ruby/rb-runt/Portfile
index c64e356c902..c92ab213cb8 100644
--- a/ruby/rb-runt/Portfile
+++ b/ruby/rb-runt/Portfile
@@ -2,9 +2,9 @@ PortSystem		1.0
 PortGroup		ruby 1.0
 PortGroup		github 1.0
 
-github.setup    mlipper runt 0_7_0 RUNT_
+github.setup    mlipper runt 0.9.0 RUNT_
 ruby.setup		runt 0.7.0 setup.rb {README doc}
-revision        1
+revision        0
 maintainers		nomaintainer
 description		Ruby API for scheduling recurring/occuring events
 long_description	Runt provides a simple API for scheduling \
@@ -13,10 +13,16 @@ long_description	Runt provides a simple API for scheduling \
 					patterns created by Martin Fowler. It is a Ruby \
 					version of ChronicJ (http://chronicj.org).
 license         Apache-1.1
-checksums		md5 8b938b318157805e2ee6279825cab324
+checksums		rmd160  308c1bd2d169f8e9f68ce0855df36fe0b008dbe4 \
+           sha256  e6496c8ecd82f88a56c8d70acebe926fa432031528a245b6ae37754b5811cfc0 \
+           size    90624
 platforms		darwin
 supported_archs	noarch
 
 test.run		yes
 test.dir		${worksrcpath}/test
 test.cmd		${ruby.bin} alltests.rb
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-simple_oauth/Portfile b/ruby/rb-simple_oauth/Portfile
index 216da330ecc..60594cfe120 100644
--- a/ruby/rb-simple_oauth/Portfile
+++ b/ruby/rb-simple_oauth/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			simple_oauth 0.1.5 gem {} rubygems
+ruby.setup			simple_oauth 0.3.1 gem {} rubygems
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			Simply builds and verifies OAuth headers
 long_description	Simply builds and verifies OAuth headers
@@ -9,8 +9,8 @@ long_description	Simply builds and verifies OAuth headers
 homepage			https://github.com/laserlemon/simple_oauth
 license				MIT
 
-checksums			md5     d46f9be42710da270687569e00ebf5a7 \
-					sha1    5a66a9e67119b2bf95ccda1e24cbc623ec8f54f2 \
-					rmd160  f6812df6e63d4572247eb475943a27cae2e9bb4d
+checksums			rmd160  b403a6ef5b1a57dcff2aa2b17cefcb403761ed55 \
+            sha256  147992e2c872c5b3cb97292e4a4ef099c9dbb76112760002ad93f1534d8c8937 \
+            size    8704
 platforms			darwin
 
diff --git a/ruby/rb-slave/Portfile b/ruby/rb-slave/Portfile
index 83b4372422c..116e5badd9c 100644
--- a/ruby/rb-slave/Portfile
+++ b/ruby/rb-slave/Portfile
@@ -1,13 +1,13 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			slave 1.2.1 gem {} rubygems
+ruby.setup			slave 1.3.2 gem {} rubygems
 maintainers			nomaintainer
 description			Ruby class to fork processes and starting a DRb server.
 long_description	${description}
-checksums			md5 7d7d7efb584b4581ad1494d2229f09c5 \
-					sha1 b6974b87307ebb0071bbd2611546e7bf6bfd3050 \
-					rmd160 2874f5e23b8c19109c7179710833fdcd0a66901e
+checksums			rmd160  5fc692fe7695890c14f016f730ae86ed03ccf1fd \
+            sha256  8b363af7b9e11540a37c90b5d9134235496cc77876ffb784886b4fd8ccb330bc \
+            size    19456
 platforms			darwin
 homepage			https://github.com/ahoward/slave
 
diff --git a/ruby/rb-snmp/Portfile b/ruby/rb-snmp/Portfile
index da42dc2b972..cbdf99a3858 100644
--- a/ruby/rb-snmp/Portfile
+++ b/ruby/rb-snmp/Portfile
@@ -3,7 +3,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          snmp 1.0.1 gem {} rubygems
+ruby.setup          snmp 1.3.2 gem {} rubygems
 platforms           darwin
 maintainers         nomaintainer
 description         SNMP library implemented in ruby
@@ -14,6 +14,13 @@ long_description    This library implements SNMP (the Simple Network \
                     net-snmp. You can run this library anywhere that Ruby \
                     can run.
 
-checksums           md5 03917ca123adb7827b2aa75304953a28
+checksums           rmd160  bb60ed683debea17c36c379b6b4cda2ab46b9861 \
+                    sha256  0e039418cac662d196e65ab91ebd794748e27da50fe4f818fe9dd7331dcf27f7 \
+                    size    206336
 
 depends_lib-append  port:rb-gem_plugin
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc
diff --git a/ruby/rb-stomp/Portfile b/ruby/rb-stomp/Portfile
index ca8c18d4791..11c44c0f65d 100644
--- a/ruby/rb-stomp/Portfile
+++ b/ruby/rb-stomp/Portfile
@@ -1,14 +1,16 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		stomp 1.1 gem {} rubygems
-revision		1
+ruby.setup		stomp 1.4.10 gem {} rubygems
+revision		0
 license			Apache-2
 maintainers		nomaintainer
 description		Ruby bindings for the stomp messaging protocol
 long_description	${description}
 platforms		darwin
 
-checksums           md5     dc082715aeac2482624167202d6739bb \
-                    sha1    668b75c954259df81f1a2e0eadab3225f8546d68 \
-                    rmd160  dc6deea6a21c277690e1965b25ffff0351407bfd
+checksums           rmd160  0870a173e0f5cc398263a117355c19843f8f832d \
+                    sha256  4ee5cb30341627a1d5d928e02353dd69e8c00e8a6301815762e253ce3a9e84af \
+                    size    99840
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rspec
diff --git a/ruby/rb-stream/Portfile b/ruby/rb-stream/Portfile
index fa2b23afed5..438dd2c63d0 100644
--- a/ruby/rb-stream/Portfile
+++ b/ruby/rb-stream/Portfile
@@ -1,13 +1,22 @@
 PortSystem		1.0
 PortGroup		ruby 1.0
 
-ruby.setup		stream 0.5 gem {} rubygems
-revision        1
+ruby.setup		stream 0.5.3 gem {} rubygems
+revision        0
 maintainers		nomaintainer
 license			{Ruby GPL-2}
 description		Extended External Iterators
 long_description	Extended External Iterators (forward and backward). \
                     Borrowed from Smalltalk stream concept where the name of \
                     the module comes from.
-checksums		md5 3e9dca987b799b1db4bd59dc713df8e9
+checksums		rmd160  96f66ef2efe7530c20df3e1aad62c5c8e2b0d3a7 \
+           sha256  b4c0441186fb4f5b47a3355007dee6ae0aec4060652688743317a5bc88e70f8f \
+           size    15360
 platforms		darwin
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-generator
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rdoc \
+                    port:rb${ruby.suffix}-test-unit \
+                    port:rb${ruby.suffix}-yard
diff --git a/ruby/rb-term-ansicolor/Portfile b/ruby/rb-term-ansicolor/Portfile
index 4047a639141..a4c1f553bec 100644
--- a/ruby/rb-term-ansicolor/Portfile
+++ b/ruby/rb-term-ansicolor/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          term-ansicolor 1.0.4 gem {} rubygems
+ruby.setup          term-ansicolor 1.7.1 gem {} rubygems
 
 license             GPL-2
 maintainers         nomaintainer
@@ -11,6 +11,12 @@ platforms           darwin
 
 homepage            https://flori.github.io/term-ansicolor/
 
-checksums           md5 19e0fd34944da6c58769d43d030a0c6c \
-                    rmd160 d637b212c193168263516fdbf99cc44b2422c90c \
-                    sha1 13164176e602bbc3d8fc83d969762bde1e3f89f8
+checksums           rmd160  534e683f7712586444f497e0ece172b8eb95f35f \
+                    sha256  92339ffec77c4bddc786a29385c91601dd52fc68feda23609bba0491229b05f7 \
+                    size    44544
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-tins
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-gem_hadar \
+                    port:rb${ruby.suffix}-simplecov \
+                    port:rb${ruby.suffix}-test-unit
diff --git a/ruby/rb-treetop/Portfile b/ruby/rb-treetop/Portfile
index ede81c9b4de..8419801640a 100644
--- a/ruby/rb-treetop/Portfile
+++ b/ruby/rb-treetop/Portfile
@@ -1,8 +1,8 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          treetop 1.4.2 gem {} rubygems
-revision            1
+ruby.setup          treetop 1.6.11 gem {} rubygems
+revision            0
 
 license             MIT
 maintainers         nomaintainer
@@ -13,6 +13,12 @@ platforms           darwin
 
 depends_lib-append  port:rb-polyglot
 
-checksums           md5 3bbf34b6eefd0549409cdb11ac000cbe \
-                    rmd160 4d069acb745d67cf47c444c986fe8a50d87000bb \
-                    sha1 389f1312ab8a117ddd8181ca921217002e0c4273
+checksums           rmd160  afdd9ae43b6e4271daa2677dcd9c5d8542337603 \
+                    sha256  102e13adf065fc916eae60b9539a76101902a56e4283c847468eaea9c2c72719 \
+                    size    91136
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-activesupport \
+                    port:rb${ruby.suffix}-i18n \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rr \
+                    port:rb${ruby.suffix}-rspec
diff --git a/ruby/rb-trollop/Portfile b/ruby/rb-trollop/Portfile
index 63a369111e6..f0634551526 100644
--- a/ruby/rb-trollop/Portfile
+++ b/ruby/rb-trollop/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          trollop 1.14 gem {} rubygems
+ruby.setup          trollop 2.9.10 gem {} rubygems
 categories-append   devel
 license             GPL-2
 maintainers         nomaintainer
@@ -10,6 +10,10 @@ long_description    ${description}
 
 platforms           darwin
 
-checksums           md5     c9ec5bf5381b38cfd441370f9c618da5 \
-                    sha1    85af2858ce2ce6733b8c4391aec2bc679df9726e \
-                    rmd160  98bcf28066412abd3fa295906daeb655c77f4059
+checksums           rmd160  d5a9a4484edde0c76dd0e28125419c43caf5b948 \
+                    sha256  ceca2d91f349163d6ee3e792d356d4ded7472e6da31ac6dcc5956d1b03607bf7 \
+                    size    29696
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-chronic \
+                    port:rb${ruby.suffix}-minitest \
+                    port:rb${ruby.suffix}-rake
diff --git a/ruby/rb-tweetstream/Portfile b/ruby/rb-tweetstream/Portfile
index 812d0cb3f4f..8f278a710b7 100644
--- a/ruby/rb-tweetstream/Portfile
+++ b/ruby/rb-tweetstream/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			tweetstream 1.0.4 gem {} rubygems
+ruby.setup			tweetstream 2.6.1 gem {} rubygems
 revision			0
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			A RubyGem to access the Twitter Streaming API.
@@ -9,9 +9,16 @@ long_description	A RubyGem to access the Twitter Streaming API.
 
 homepage			https://github.com/intridea/tweetstream
 license				MIT
-depends_lib-append	port:rb-twitter-stream	port:rb-daemons
-checksums			md5     d1d73e3f2ea8cff65a092497d7bf72bc \
-					sha1    05f94a47502ee7aa520847cc89a90f2441f47b9f \
-					rmd160  a1e77474c4391105c300dce42666290d2e9c1a76
+depends_lib-append	port:rb-twitter-stream \
+                  	port:rb-daemons \
+                  	port:rb${ruby.suffix}-em-http-request \
+                  	port:rb${ruby.suffix}-em-twitter \
+                  	port:rb${ruby.suffix}-multi_json \
+                  	port:rb${ruby.suffix}-twitter
+checksums			rmd160  6fbdb0cde25591d9584b59a7366146e81212c794 \
+            sha256  9f9603f5e5ac3cb73f8b9751616e563015bf28d8aeb4a1aad7027e29684924af \
+            size    36352
 platforms			darwin
 
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-bundler
diff --git a/ruby/rb-twitter-stream/Portfile b/ruby/rb-twitter-stream/Portfile
index faa129acdcd..765dfb71a1e 100644
--- a/ruby/rb-twitter-stream/Portfile
+++ b/ruby/rb-twitter-stream/Portfile
@@ -1,7 +1,7 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			twitter-stream 0.1.14 gem {} rubygems
+ruby.setup			twitter-stream 0.1.16 gem {} rubygems
 license				MIT
 maintainers			{kimuraw @kimuraw} openmaintainer
 description			Simple Ruby client library for twitter streaming API.
@@ -11,9 +11,10 @@ long_description	Simple Ruby client library for twitter streaming API. \
 
 homepage			https://github.com/voloko/twitter-stream
 depends_lib-append	port:rb-eventmachine \
-					port:rb-simple_oauth port:rb-http_parser	
+					port:rb-simple_oauth \
+					port:rb-http_parser
 
-checksums			md5     dfb7a7548a0d54f5affc05136a339f58 \
-					sha1    7947e8df96408e1fd535ae82bf632997f7534702 \
-					rmd160  f118795035fe8f326c32939e82a32e315955d744
+checksums			rmd160  ae3242c063df7e855f9b1276811ad2e74cd9bdb1 \
+            sha256  3866afdfbdf083e773b46afb3037ff3e3b1ebf8014ab88353153daddc70b4847 \
+            size    13312
 platforms			darwin
diff --git a/ruby/rb-uuidtools/Portfile b/ruby/rb-uuidtools/Portfile
index c64476576b6..db252e58ae7 100644
--- a/ruby/rb-uuidtools/Portfile
+++ b/ruby/rb-uuidtools/Portfile
@@ -1,7 +1,7 @@
 PortSystem          1.0
 PortGroup           ruby 1.0
 
-ruby.setup          uuidtools 1.0.4 gem {} rubygems
+ruby.setup          uuidtools 2.2.0 gem {} rubygems
 
 maintainers         devclue.com:blair openmaintainer
 license             MIT
@@ -12,6 +12,11 @@ long_description    UUIDTools was designed to be a simple library for \
                     whenever possible.
 platforms           darwin
 
-checksums           md5 6a4b126b4e20192ad75955a886640dbc \
-                    rmd160 7bb0cb77a36eb97372dd8713035ca66bf482f530 \
-                    sha1 273584ecc69e9957963a7c93e91d43edc1924e79
+checksums           rmd160  3c22eeae505d4ad6b4f154e108b6f3c7786ac3fa \
+                    sha256  c4aed168141746d2357ce907626b83998084aeb3c6ac16670ae902a462191069 \
+                    size    27136
+# TODO: Move this
+depends_test-append port:rb${ruby.suffix}-launchy \
+                    port:rb${ruby.suffix}-rake \
+                    port:rb${ruby.suffix}-rspec \
+                    port:rb${ruby.suffix}-yard
diff --git a/ruby/rb-webgen/Portfile b/ruby/rb-webgen/Portfile
index 281de872b10..b215a3d2e1f 100644
--- a/ruby/rb-webgen/Portfile
+++ b/ruby/rb-webgen/Portfile
@@ -2,7 +2,7 @@ PortSystem      1.0
 PortGroup       ruby 1.0
 
 ruby.branches   2.7
-ruby.setup      webgen 1.7.0 gem
+ruby.setup      webgen 1.7.2 gem
 license         GPL-3
 maintainers     nomaintainer
 description     Templated based static website generator
@@ -11,7 +11,9 @@ long_description    Webgen is a web page generator implemented in Ruby. \
                     templates and page description files.
 categories-append   www
 homepage        https://webgen.gettalong.org/
-checksums       md5 08d5e773c6fd700e41b868053ea9493f
+checksums       rmd160  70e847d6336f975ef7142d7bc0c1d150a2f79435 \
+                sha256  7578ac38ee2445a997188347e1f0b469d4e0da79f18b9f964ba5e47ef7d56ee1 \
+                size    201728
 platforms       darwin
 supported_archs noarch
 
diff --git a/ruby/rb-xml-simple/Portfile b/ruby/rb-xml-simple/Portfile
index 3fa1fcfafbc..14a7678b300 100644
--- a/ruby/rb-xml-simple/Portfile
+++ b/ruby/rb-xml-simple/Portfile
@@ -1,13 +1,15 @@
 PortSystem			1.0
 PortGroup			ruby 1.0
 
-ruby.setup			xml-simple 1.0.11 gem {} rubygems
+ruby.setup			xml-simple 1.1.9 gem {} rubygems
 license				{Ruby GPL-2}
 maintainers			nomaintainer
 description			A very simple API for XML processing.
 long_description	${description}
-checksums			md5 73cda917a0b84f9e97cde65d4587fb18 \
-					sha1 1d563f56bf425b9400abf031eb6091c81221819b \
-					rmd160 55e3156735c96a111f268804861732d43e914476
+checksums			rmd160  966801ee87943b12ed49ed8f8f72e88a419f855d \
+            sha256  d21131e519c86f1a5bc2b6d2d57d46e6998e47f18ed249b25cad86433dbd695d \
+            size    12288
 platforms			darwin
 homepage			https://github.com/maik/xml-simple
+# TODO: Move this
+depends_lib-append port:rb${ruby.suffix}-rexml