diff --git a/sysutils/rubygem-bolt/Makefile b/sysutils/rubygem-bolt/Makefile
index 471ea9027d99..068a912eb7a9 100644
--- a/sysutils/rubygem-bolt/Makefile
+++ b/sysutils/rubygem-bolt/Makefile
@@ -1,59 +1,59 @@
 PORTNAME=	bolt
-PORTVERSION=	3.27.1
+PORTVERSION=	3.27.2
 CATEGORIES=	sysutils rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	puppet@FreeBSD.org
 COMMENT=	Execute commands remotely over SSH and WinRM
 WWW=		https://github.com/puppetlabs/bolt
 
 LICENSE=	APACHE20
 
 RUN_DEPENDS=	r10k:sysutils/rubygem-r10k \
 		rubygem-addressable>=2.5:www/rubygem-addressable \
 		rubygem-aws-sdk-ec2>1:devel/rubygem-aws-sdk-ec2 \
 		rubygem-CFPropertyList>=2.2:devel/rubygem-CFPropertyList \
 		rubygem-concurrent-ruby11>=1.0:devel/rubygem-concurrent-ruby11 \
 		rubygem-ffi>=1.13:devel/rubygem-ffi \
 		rubygem-hiera-eyaml>=3:sysutils/rubygem-hiera-eyaml \
 		rubygem-jwt>=2.2:www/rubygem-jwt \
 		rubygem-logging>=2.2:devel/rubygem-logging \
 		rubygem-net-scp1>=1.2<2:security/rubygem-net-scp1 \
 		rubygem-net-ssh>=4.0:security/rubygem-net-ssh \
 		rubygem-net-ssh-krb>=0.5:security/rubygem-net-ssh-krb \
 		rubygem-orchestrator_client>=0.5:net/rubygem-orchestrator_client \
 		rubygem-puppet-resource_api>=1.8.1:devel/rubygem-puppet-resource_api \
 		rubygem-puppet-strings>=2.3:textproc/rubygem-puppet-strings \
 		rubygem-puppetfile-resolver>=0.6.2:sysutils/rubygem-puppetfile-resolver \
 		rubygem-ruby_smb>=1.0:net/rubygem-ruby_smb \
 		rubygem-terminal-table>=3.0<4:textproc/rubygem-terminal-table \
 		rubygem-winrm-fs>=1.3:sysutils/rubygem-winrm-fs \
 		rubygem-winrm>=2.0:sysutils/rubygem-winrm
 
 USES=		gem shebangfix
 
 ruby_OLD_CMD+=	/opt/puppetlabs/puppet/bin/ruby
 SHEBANG_FILES=	libexec/*
 
 NO_ARCH=	yes
 
 PLIST_FILES=	bin/bolt \
 		etc/bash_completion.d/bolt
 
 OPTIONS_SINGLE=	PUPPET
 OPTIONS_SINGLE_PUPPET=PUPPET6 PUPPET7 PUPPET8
 OPTIONS_DEFAULT=PUPPET7
 
 PUPPET6_DESC=	Depend on sysutils/puppet6
 PUPPET7_DESC=	Depend on sysutils/puppet7
 PUPPET8_DESC=	Depend on sysutils/puppet8
 
 PUPPET6_RUN_DEPENDS=puppet:sysutils/puppet6
 PUPPET7_RUN_DEPENDS=puppet:sysutils/puppet7
 PUPPET8_RUN_DEPENDS=puppet:sysutils/puppet8
 
 post-install:
 	${MKDIR} ${STAGEDIR}${PREFIX}/etc/bash_completion.d
 	${INSTALL_DATA} ${WRKSRC}/resources/bolt_bash_completion.sh ${STAGEDIR}${PREFIX}/etc/bash_completion.d/bolt
 
 .include <bsd.port.mk>
diff --git a/sysutils/rubygem-bolt/distinfo b/sysutils/rubygem-bolt/distinfo
index efc300f42839..ed707e90f430 100644
--- a/sysutils/rubygem-bolt/distinfo
+++ b/sysutils/rubygem-bolt/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1679083831
-SHA256 (rubygem/bolt-3.27.1.gem) = 611e84dcf9e280a1db41ca23488521283942d4a66f8e9d8fc7708dd387111e1b
-SIZE (rubygem/bolt-3.27.1.gem) = 250368
+TIMESTAMP = 1692985910
+SHA256 (rubygem/bolt-3.27.2.gem) = fc37b7a613ce1a40e97793f60a1ab26af631d2793d350585dd76e8a4f6053097
+SIZE (rubygem/bolt-3.27.2.gem) = 250368
diff --git a/sysutils/rubygem-bolt/files/patch-bolt.gemspec b/sysutils/rubygem-bolt/files/patch-bolt.gemspec
index 80719f7dbb90..e2127240b019 100644
--- a/sysutils/rubygem-bolt/files/patch-bolt.gemspec
+++ b/sysutils/rubygem-bolt/files/patch-bolt.gemspec
@@ -1,20 +1,11 @@
---- bolt.gemspec.orig	2023-03-24 20:53:49 UTC
+--- bolt.gemspec.orig	2023-08-25 18:06:17 UTC
 +++ bolt.gemspec
-@@ -24,7 +24,7 @@ Gem::Specification.new do |s|
- 
-   s.add_runtime_dependency(%q<addressable>.freeze, ["~> 2.5"])
-   s.add_runtime_dependency(%q<aws-sdk-ec2>.freeze, ["~> 1"])
--  s.add_runtime_dependency(%q<CFPropertyList>.freeze, ["~> 2.2"])
-+  s.add_runtime_dependency(%q<CFPropertyList>.freeze, [">= 2.2"])
-   s.add_runtime_dependency(%q<concurrent-ruby>.freeze, ["~> 1.0", "< 1.2.0"])
-   s.add_runtime_dependency(%q<ffi>.freeze, [">= 1.9.25", "< 2.0.0"])
-   s.add_runtime_dependency(%q<hiera-eyaml>.freeze, ["~> 3"])
 @@ -40,7 +40,7 @@ Gem::Specification.new do |s|
    s.add_runtime_dependency(%q<puppet-resource_api>.freeze, [">= 1.8.1"])
-   s.add_runtime_dependency(%q<puppet-strings>.freeze, [">= 2.3.0", "< 4.0"])
+   s.add_runtime_dependency(%q<puppet-strings>.freeze, [">= 2.3.0", "< 5.0"])
    s.add_runtime_dependency(%q<r10k>.freeze, ["~> 3.10"])
 -  s.add_runtime_dependency(%q<ruby_smb>.freeze, ["~> 1.0"])
 +  s.add_runtime_dependency(%q<ruby_smb>.freeze, [">= 1.0", "< 4.0"])
    s.add_runtime_dependency(%q<terminal-table>.freeze, ["~> 3.0"])
    s.add_runtime_dependency(%q<winrm>.freeze, ["~> 2.0"])
    s.add_runtime_dependency(%q<winrm-fs>.freeze, ["~> 1.3"])