diff --git a/devel/ruby-gems/Makefile b/devel/ruby-gems/Makefile
index 4776e9bb7de0..7a71e311246a 100644
--- a/devel/ruby-gems/Makefile
+++ b/devel/ruby-gems/Makefile
@@ -6,7 +6,7 @@
 # - www/rubygem-gitlab-grack/files/patch-gemspec
 
 PORTNAME=	gems
-PORTVERSION=	2.6.14
+PORTVERSION=	2.7.4
 CATEGORIES=	devel ruby
 MASTER_SITES=	http://production.cf.rubygems.org/rubygems/
 PKGNAMEPREFIX=	${RUBY_PKGNAMEPREFIX}
@@ -36,6 +36,7 @@ GEMS_DOC_BASE_DIR_P=	${GEMS_VER_DIR_P}/doc
 GEMS_DOC_DIR=		${GEMS_DOC_BASE_DIR}/${DISTNAME}
 GEMS_DOC_DIR_P=		${GEMS_DOC_BASE_DIR_P}/%%DISTNAME%%
 GEMS_ENV=		GEM_HOME=${STAGEDIR}${PREFIX}/${GEMS_VER_DIR}
+RUBY_SETUP_OPTIONS=	--destdir=${STAGEDIR} --no-regenerate-binstubs
 RUBY_VER_SHORT=		${RUBY_VER:S/.//}
 
 GEMS_DIR=		${GEMS_VER_DIR}/gems
@@ -54,8 +55,11 @@ PLIST_SUB=	DISTNAME="${DISTNAME}" \
 
 OPTIONS_DEFINE=	DOCS
 
-DOCS_VARS_OFF=		RUBY_SETUP_OPTIONS="--destdir=${STAGEDIR} --no-ri --no-rdoc"
-DOCS_VARS=		RUBY_SETUP_OPTIONS="--destdir=${STAGEDIR}"
+DOCS_VARS_OFF=	RUBY_SETUP_OPTIONS+="--no-ri --no-rdoc"
+
+post-patch:
+# Disable bundler for gemdeps
+	@${REINPLACE_CMD} -e '/USE_BUNDLER_FOR_GEMDEPS = true/ s|true|false|' ${WRKSRC}/lib/rubygems.rb
 
 do-install:
 	cd ${WRKSRC}/ && ${SETENV} ${GEMS_ENV} ${RUBY} ${RUBY_SETUP} ${RUBY_SETUP_OPTIONS}
diff --git a/devel/ruby-gems/distinfo b/devel/ruby-gems/distinfo
index a23fc3fee8cc..45f3ee386f22 100644
--- a/devel/ruby-gems/distinfo
+++ b/devel/ruby-gems/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1507626380
-SHA256 (ruby/rubygems-2.6.14.tgz) = 406a45d258707f52241843e9c7902bbdcf00e7edc3e88cdb79c46659b47851ec
-SIZE (ruby/rubygems-2.6.14.tgz) = 769418
+TIMESTAMP = 1514381323
+SHA256 (ruby/rubygems-2.7.4.tgz) = bbe35ce6646e4168fcb1071d5f83b2d1154924f5150df0f5fca0f37d2583a182
+SIZE (ruby/rubygems-2.7.4.tgz) = 908282
diff --git a/devel/ruby-gems/pkg-plist b/devel/ruby-gems/pkg-plist
index 6fed5207da18..4e18588ed0b1 100644
--- a/devel/ruby-gems/pkg-plist
+++ b/devel/ruby-gems/pkg-plist
@@ -3,6 +3,7 @@ bin/gem%%RUBY_VER_SHORT%%
 %%RUBY_SITELIBDIR%%/rubygems.rb
 %%RUBY_SITELIBDIR%%/rubygems/available_set.rb
 %%RUBY_SITELIBDIR%%/rubygems/basic_specification.rb
+%%RUBY_SITELIBDIR%%/rubygems/bundler_version_finder.rb
 %%RUBY_SITELIBDIR%%/rubygems/command.rb
 %%RUBY_SITELIBDIR%%/rubygems/command_manager.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/build_command.rb
@@ -29,6 +30,8 @@ bin/gem%%RUBY_VER_SHORT%%
 %%RUBY_SITELIBDIR%%/rubygems/commands/search_command.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/server_command.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/setup_command.rb
+%%RUBY_SITELIBDIR%%/rubygems/commands/signin_command.rb
+%%RUBY_SITELIBDIR%%/rubygems/commands/signout_command.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/sources_command.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/specification_command.rb
 %%RUBY_SITELIBDIR%%/rubygems/commands/stale_command.rb
@@ -148,6 +151,7 @@ bin/gem%%RUBY_VER_SHORT%%
 %%RUBY_SITELIBDIR%%/rubygems/security/policy.rb
 %%RUBY_SITELIBDIR%%/rubygems/security/signer.rb
 %%RUBY_SITELIBDIR%%/rubygems/security/trust_dir.rb
+%%RUBY_SITELIBDIR%%/rubygems/security_option.rb
 %%RUBY_SITELIBDIR%%/rubygems/server.rb
 %%RUBY_SITELIBDIR%%/rubygems/source.rb
 %%RUBY_SITELIBDIR%%/rubygems/source/git.rb
diff --git a/security/rubygem-ezcrypto/files/patch-gemspec b/security/rubygem-ezcrypto/files/patch-gemspec
index 59ad6d85cefc..ac53853c83a0 100644
--- a/security/rubygem-ezcrypto/files/patch-gemspec
+++ b/security/rubygem-ezcrypto/files/patch-gemspec
@@ -9,7 +9,7 @@
    s.homepage = "http://ezcrypto.rubyforge.org".freeze
    s.requirements = ["none".freeze]
    s.rubyforge_project = "ezcrypto".freeze
-   s.rubygems_version = "2.6.14".freeze
+   s.rubygems_version = "2.7.4".freeze
    s.summary = "Simplified encryption library.".freeze
 -  s.test_files = ["test/active_crypto_test.rb".freeze, "test/agree2.com.cert".freeze, "test/association_key_holder_test.rb".freeze, "test/database.yml".freeze, "test/debug.log".freeze, "test/digest_test.rb".freeze, "test/dsakey.pem".freeze, "test/dsapubkey.pem".freeze, "test/dsig_test.rb".freeze, "test/encrypt_test.rb".freeze, "test/ezcrypto_test.rb".freeze, "test/key_holder_test.rb".freeze, "test/protectedsigner.pem".freeze, "test/sf-class2-root.crt".freeze, "test/sf_intermediate.crt".freeze, "test/store".freeze, "test/test_helper.rb".freeze, "test/testchild.pem".freeze, "test/testchild.req".freeze, "test/testpub.pem".freeze, "test/testsigner.cert".freeze, "test/testsigner.pem".freeze, "test/valicert_class2_root.crt".freeze]
 +  s.test_files = ["test/active_crypto_test.rb".freeze, "test/agree2.com.cert".freeze, "test/association_key_holder_test.rb".freeze, "test/database.yml".freeze, "test/debug.log".freeze, "test/digest_test.rb".freeze, "test/dsakey.pem".freeze, "test/dsapubkey.pem".freeze, "test/dsig_test.rb".freeze, "test/encrypt_test.rb".freeze, "test/ezcrypto_test.rb".freeze, "test/key_holder_test.rb".freeze, "test/protectedsigner.pem".freeze, "test/sf-class2-root.crt".freeze, "test/sf_intermediate.crt".freeze, "test/test_helper.rb".freeze, "test/testchild.pem".freeze, "test/testchild.req".freeze, "test/testpub.pem".freeze, "test/testsigner.cert".freeze, "test/testsigner.pem".freeze, "test/valicert_class2_root.crt".freeze]
diff --git a/www/rubygem-gitlab-grack/files/patch-gemspec b/www/rubygem-gitlab-grack/files/patch-gemspec
index 8dcd18da41b4..18399b3d685f 100644
--- a/www/rubygem-gitlab-grack/files/patch-gemspec
+++ b/www/rubygem-gitlab-grack/files/patch-gemspec
@@ -8,5 +8,5 @@
 -  s.files = [".gitignore".freeze, ".gitmodules".freeze, ".travis.yml".freeze, "CHANGELOG".freeze, "Gemfile".freeze, "Gemfile.lock".freeze, "README.md".freeze, "Rakefile".freeze, "bin/console".freeze, "bin/testserver".freeze, "examples/dispatch.fcgi".freeze, "grack.gemspec".freeze, "install.txt".freeze, "lib/grack.rb".freeze, "lib/grack/auth.rb".freeze, "lib/grack/bundle.rb".freeze, "lib/grack/git.rb".freeze, "lib/grack/server.rb".freeze, "lib/grack/version.rb".freeze, "tests/main_test.rb".freeze]
 +  s.files = [".gitignore".freeze, ".gitmodules".freeze, ".travis.yml".freeze, "CHANGELOG".freeze, "Gemfile".freeze, "Gemfile.lock".freeze, "README.md".freeze, "Rakefile".freeze, "examples/dispatch.fcgi".freeze, "grack.gemspec".freeze, "install.txt".freeze, "lib/grack.rb".freeze, "lib/grack/auth.rb".freeze, "lib/grack/bundle.rb".freeze, "lib/grack/git.rb".freeze, "lib/grack/server.rb".freeze, "lib/grack/version.rb".freeze, "tests/main_test.rb".freeze]
    s.homepage = "https://github.com/gitlabhq/grack".freeze
-   s.rubygems_version = "2.6.14".freeze
+   s.rubygems_version = "2.7.4".freeze
    s.summary = "Ruby/Rack Git Smart-HTTP Server Handler".freeze