diff --git a/sysutils/rubygem-bolt/Makefile b/sysutils/rubygem-bolt/Makefile
index b704d852dafc..93a389959d5c 100644
--- a/sysutils/rubygem-bolt/Makefile
+++ b/sysutils/rubygem-bolt/Makefile
@@ -1,58 +1,58 @@
 PORTNAME=	bolt
-PORTVERSION=	3.20.0
+PORTVERSION=	3.21.0
 CATEGORIES=	sysutils rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	puppet@FreeBSD.org
 COMMENT=	Execute commands remotely over SSH and WinRM
 
 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-ffi>=1.13:devel/rubygem-ffi \
 		rubygem-concurrent-ruby>=1.0:devel/rubygem-concurrent-ruby \
 		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-paint>=2.2:devel/rubygem-paint \
 		rubygem-puppet-resource_api>=1.8.1:devel/rubygem-puppet-resource_api \
 		rubygem-puppet-strings>=2.3:textproc/rubygem-puppet-strings \
 		rubygem-puppetfile-resolver>=0.1: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
 USE_RUBY=	yes
 
 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
 OPTIONS_DEFAULT=PUPPET7
 
 PUPPET6_DESC=	Depend on sysutils/puppet6
 PUPPET7_DESC=	Depend on sysutils/puppet7
 
 PUPPET6_RUN_DEPENDS=puppet:sysutils/puppet6
 PUPPET7_RUN_DEPENDS=puppet:sysutils/puppet7
 
 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 ba9bbfd50ae2..23968b48abe1 100644
--- a/sysutils/rubygem-bolt/distinfo
+++ b/sysutils/rubygem-bolt/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1636411053
-SHA256 (rubygem/bolt-3.20.0.gem) = 5eea7ba465c0c7ef9ae3bc3c9c8c8d9c0c2a14cf74a3c12246c4b6dad146754e
-SIZE (rubygem/bolt-3.20.0.gem) = 242176
+TIMESTAMP = 1640368088
+SHA256 (rubygem/bolt-3.21.0.gem) = 9ab8c5cf3011b5d06a75f68e68f5f4d281bf0a1c15c07c92372b55ecc42714ea
+SIZE (rubygem/bolt-3.21.0.gem) = 244736