diff --git a/devel/ruby-gems/Makefile b/devel/ruby-gems/Makefile
index 44bd5773cc87..93b043d02727 100644
--- a/devel/ruby-gems/Makefile
+++ b/devel/ruby-gems/Makefile
@@ -1,73 +1,73 @@
 PORTNAME=	gems
-PORTVERSION=	3.4.19
+PORTVERSION=	3.4.20
 CATEGORIES=	devel ruby
 MASTER_SITES=	https://rubygems.org/rubygems/
 PKGNAMEPREFIX=	${RUBY_PKGNAMEPREFIX}
 DISTNAME=	rubygems-${PORTVERSION}
 DIST_SUBDIR=	ruby
 
 MAINTAINER=	ruby@FreeBSD.org
 COMMENT=	Package management framework for the Ruby language
 WWW=		https://rubygems.org/
 
 LICENSE=	MIT RUBY
 LICENSE_COMB=	dual
 LICENSE_FILE_MIT=	${WRKSRC}/MIT.txt
 LICENSE_FILE_RUBY=	${WRKSRC}/LICENSE.txt
 
 USES=		cpe ruby tar:tgz
 
 GEMS_BASE_DIR=	lib/ruby/gems/${RUBY_VER}
 GEMS_ENV=	GEM_HOME=${STAGEDIR}${PREFIX}/${GEMS_BASE_DIR}
 NO_ARCH=	yes
 NO_BUILD=	yes
 RUBY_SETUP=	setup.rb
 RUBY_SETUP_OPTIONS=	--destdir=${STAGEDIR} \
 			--no-format-executable \
 			--no-regenerate-binstubs \
 			--no-regenerate-plugins
 
 CACHE_DIR=	${GEMS_BASE_DIR}/cache
 DOC_DIR=	${GEMS_BASE_DIR}/doc
 EXT_DIR=	${GEMS_BASE_DIR}/extensions
 GEMS_DIR=	${GEMS_BASE_DIR}/gems
 PLUGINS_DIR=	${GEMS_BASE_DIR}/plugins
 SPEC_DIR=	${GEMS_BASE_DIR}/specifications
 
 PLIST_SUB=	CACHE_DIR="${CACHE_DIR}" \
 		DOC_DIR="${DOC_DIR}" \
 		EXT_DIR="${EXT_DIR}" \
 		GEMS_DIR="${GEMS_DIR}" \
 		PLUGINS_DIR="${PLUGINS_DIR}" \
 		SPEC_DIR="${SPEC_DIR}"
 
 CPE_VENDOR=	rubygems
 CPE_PRODUCT=	rubygems
 
 OPTIONS_DEFINE=	DOCS
 
 DOCS_VARS_OFF=	RUBY_SETUP_OPTIONS+="--no-ri --no-rdoc"
 
 post-extract:
 	@${RM} -r ${WRKSRC}/bundler
 	@${FIND} ${WRKSRC} -name .document -delete
 
 post-patch:
 	@${RM} ${WRKSRC}/lib/rubygems/commands/setup_command.rb.orig
 
 do-install:
 	${MKDIR} ${STAGEDIR}${PREFIX}/${GEMS_BASE_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${GEMS_BASE_DIR}/build_info
 	${MKDIR} ${STAGEDIR}${PREFIX}/${CACHE_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${DOC_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${EXT_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${GEMS_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${PLUGINS_DIR}
 	${MKDIR} ${STAGEDIR}${PREFIX}/${SPEC_DIR}
 	cd ${WRKSRC}/ && ${SETENV} ${GEMS_ENV} ${RUBY} ${RUBY_SETUP} ${RUBY_SETUP_OPTIONS}
 
 # Find all RDOC and RI files
 post-install-DOCS-on:
 	cd ${STAGEDIR}${PREFIX}/ && ${FIND} -ds ${DOC_DIR}/ ! -type d >> ${TMPPLIST}
 
 .include <bsd.port.mk>
diff --git a/devel/ruby-gems/distinfo b/devel/ruby-gems/distinfo
index c5a48f528d3f..0a33da1a1dbc 100644
--- a/devel/ruby-gems/distinfo
+++ b/devel/ruby-gems/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1692362954
-SHA256 (ruby/rubygems-3.4.19.tgz) = f996294bd50e075eaa0a386b2b0146067e37b7728d3affd022b2ca20f032c16b
-SIZE (ruby/rubygems-3.4.19.tgz) = 1331273
+TIMESTAMP = 1696011562
+SHA256 (ruby/rubygems-3.4.20.tgz) = f6328a79feca3e749880a6f7cdfd4b6ae945049b83a58ea958e2474a91ba1f3b
+SIZE (ruby/rubygems-3.4.20.tgz) = 1340911
diff --git a/devel/rubygem-ruby_dep/files/patch-gemspec b/devel/rubygem-ruby_dep/files/patch-gemspec
index 032793a35cfe..3f667299943b 100644
--- a/devel/rubygem-ruby_dep/files/patch-gemspec
+++ b/devel/rubygem-ruby_dep/files/patch-gemspec
@@ -1,11 +1,11 @@
 --- ruby_dep.gemspec.orig	2023-01-05 20:14:42 UTC
 +++ ruby_dep.gemspec
 @@ -15,7 +15,7 @@ Gem::Specification.new do |s|
    s.files = [".gitignore".freeze, ".rspec".freeze, ".rubocop.yml".freeze, ".travis.yml".freeze, "LICENSE.txt".freeze, "README.md".freeze, "lib/ruby_dep.rb".freeze, "lib/ruby_dep/logger.rb".freeze, "lib/ruby_dep/quiet.rb".freeze, "lib/ruby_dep/ruby_version.rb".freeze, "lib/ruby_dep/travis.rb".freeze, "lib/ruby_dep/travis/ruby_version.rb".freeze, "lib/ruby_dep/version.rb".freeze, "lib/ruby_dep/warning.rb".freeze]
    s.homepage = "https://github.com/e2/ruby_dep".freeze
    s.licenses = ["MIT".freeze]
 -  s.required_ruby_version = Gem::Requirement.new(["~> 2.2".freeze, ">= 2.2.5".freeze])
 +  s.required_ruby_version = Gem::Requirement.new([">= 2.2".freeze, ">= 2.2.5".freeze])
-   s.rubygems_version = "3.4.19".freeze
+   s.rubygems_version = "3.4.20".freeze
    s.summary = "Extracts supported Ruby versions from Travis file".freeze
  
diff --git a/devel/rubygem-xdg3/files/patch-gemspec b/devel/rubygem-xdg3/files/patch-gemspec
index b5f76b1c7d41..cadb0fa48995 100644
--- a/devel/rubygem-xdg3/files/patch-gemspec
+++ b/devel/rubygem-xdg3/files/patch-gemspec
@@ -1,11 +1,11 @@
 --- xdg.gemspec.orig	2023-01-05 20:29:34 UTC
 +++ xdg.gemspec
 @@ -16,7 +16,7 @@ Gem::Specification.new do |s|
    s.files = ["LICENSE.md".freeze, "README.md".freeze, "lib/xdg.rb".freeze, "lib/xdg/cache.rb".freeze, "lib/xdg/config.rb".freeze, "lib/xdg/data.rb".freeze, "lib/xdg/environment.rb".freeze, "lib/xdg/identity.rb".freeze, "lib/xdg/pair.rb".freeze, "lib/xdg/paths/combined.rb".freeze, "lib/xdg/paths/directory.rb".freeze, "lib/xdg/paths/standard.rb".freeze]
    s.homepage = "https://github.com/bkuhlmann/xdg".freeze
    s.licenses = ["Apache-2.0".freeze]
 -  s.required_ruby_version = Gem::Requirement.new("~> 2.6".freeze)
 +  s.required_ruby_version = Gem::Requirement.new(">= 2.6".freeze)
-   s.rubygems_version = "3.4.19".freeze
+   s.rubygems_version = "3.4.20".freeze
    s.summary = "Provides an implementation of the XDG Base Directory Specification.".freeze
  
diff --git a/devel/rubygem-xdg4/files/patch-gemspec b/devel/rubygem-xdg4/files/patch-gemspec
index 8a007f553c27..33b6d6f24e5b 100644
--- a/devel/rubygem-xdg4/files/patch-gemspec
+++ b/devel/rubygem-xdg4/files/patch-gemspec
@@ -1,11 +1,11 @@
 --- xdg.gemspec.orig	2023-01-05 20:31:09 UTC
 +++ xdg.gemspec
 @@ -16,7 +16,7 @@ Gem::Specification.new do |s|
    s.files = ["LICENSE.adoc".freeze, "README.adoc".freeze, "lib/xdg.rb".freeze, "lib/xdg/cache.rb".freeze, "lib/xdg/config.rb".freeze, "lib/xdg/data.rb".freeze, "lib/xdg/environment.rb".freeze, "lib/xdg/identity.rb".freeze, "lib/xdg/pair.rb".freeze, "lib/xdg/paths/combined.rb".freeze, "lib/xdg/paths/directory.rb".freeze, "lib/xdg/paths/home.rb".freeze]
    s.homepage = "https://www.alchemists.io/projects/xdg".freeze
    s.licenses = ["Apache-2.0".freeze]
 -  s.required_ruby_version = Gem::Requirement.new("~> 2.7".freeze)
 +  s.required_ruby_version = Gem::Requirement.new(">= 2.7".freeze)
-   s.rubygems_version = "3.4.19".freeze
+   s.rubygems_version = "3.4.20".freeze
    s.summary = "Provides an implementation of the XDG Base Directory Specification.".freeze
  end