diff --git a/sysutils/rubygem-openbolt/Makefile b/sysutils/rubygem-openbolt/Makefile
index 9fa20587c1f9..77208e2cd9b4 100644
--- a/sysutils/rubygem-openbolt/Makefile
+++ b/sysutils/rubygem-openbolt/Makefile
@@ -1,51 +1,52 @@
 PORTNAME=	openbolt
-PORTVERSION=	5.4.0
+PORTVERSION=	5.5.0
 CATEGORIES=	sysutils rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	puppet@FreeBSD.org
 COMMENT=	Execute commands remotely over SSH and WinRM
 WWW=		https://github.com/OpenVoxProject/openbolt/
 
 LICENSE=	APACHE20
 
 RUN_DEPENDS=	puppet:sysutils/openvox-agent8 \
 		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-choria-mcorpc-support>=2.26:sysutils/rubygem-choria-mcorpc-support \
 		rubygem-concurrent-ruby11>=1.0:devel/rubygem-concurrent-ruby11 \
 		rubygem-ffi>=1.13<2:devel/rubygem-ffi \
 		rubygem-hiera-eyaml>=3:sysutils/rubygem-hiera-eyaml \
 		rubygem-json>=2.12.0:devel/rubygem-json \
 		rubygem-jwt>=2.2:www/rubygem-jwt \
 		rubygem-logging>=2.2:devel/rubygem-logging \
 		rubygem-minitar>=0.6:archivers/rubygem-minitar \
 		rubygem-net-scp>=1.2<5:security/rubygem-net-scp \
 		rubygem-net-ssh6>=4.0<8:security/rubygem-net-ssh6 \
 		rubygem-net-ssh-krb>=0.5:security/rubygem-net-ssh-krb \
 		rubygem-openvox-strings>=5.0:textproc/rubygem-openvox-strings \
 		rubygem-orchestrator_client>=0.5:net/rubygem-orchestrator_client \
 		rubygem-puppet-resource_api>=1.8.1:devel/rubygem-puppet-resource_api \
 		rubygem-puppetfile-resolver>=0.6.2:sysutils/rubygem-puppetfile-resolver \
 		rubygem-ruby_smb>=1.0:net/rubygem-ruby_smb \
-		rubygem-terminal-table3>=3.0<4:textproc/rubygem-terminal-table3 \
+		rubygem-terminal-table>=4.0<5:textproc/rubygem-terminal-table \
 		rubygem-winrm-fs>=1.3:filesystems/rubygem-winrm-fs \
 		rubygem-winrm>=2.0:sysutils/rubygem-winrm
 
 USES=		gem shebangfix
 
 CONFLICTS_INSTALL=	rubygem-bolt
 ruby_OLD_CMD+=	/opt/puppetlabs/puppet/bin/ruby
 SHEBANG_FILES=	libexec/*
 
 NO_ARCH=	yes
 
 PLIST_FILES=	bin/bolt \
 		etc/bash_completion.d/bolt
 
 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-openbolt/distinfo b/sysutils/rubygem-openbolt/distinfo
index 5b908c1597cc..c9d083eb2d32 100644
--- a/sysutils/rubygem-openbolt/distinfo
+++ b/sysutils/rubygem-openbolt/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1773273589
-SHA256 (rubygem/openbolt-5.4.0.gem) = f0c41c464d136e07bcd2143e86c41b1ee1ef99e7abff6e376a5217ab822ae5bc
-SIZE (rubygem/openbolt-5.4.0.gem) = 231424
+TIMESTAMP = 1779124105
+SHA256 (rubygem/openbolt-5.5.0.gem) = 3e90a8941bd99801948f16e10b32c7c2a9e816d4c36b865389d839ab939becd6
+SIZE (rubygem/openbolt-5.5.0.gem) = 252416
diff --git a/sysutils/rubygem-openbolt/files/patch-openbolt.gemspec b/sysutils/rubygem-openbolt/files/patch-openbolt.gemspec
index 15da2af2f3b6..34b6c9448a2f 100644
--- a/sysutils/rubygem-openbolt/files/patch-openbolt.gemspec
+++ b/sysutils/rubygem-openbolt/files/patch-openbolt.gemspec
@@ -1,11 +1,11 @@
---- openbolt.gemspec.orig	2025-12-17 07:59:46 UTC
+--- openbolt.gemspec.orig	2026-05-18 17:54:35 UTC
 +++ openbolt.gemspec
-@@ -40,7 +40,7 @@ Gem::Specification.new do |s|
+@@ -41,7 +41,7 @@ Gem::Specification.new do |s|
    s.add_runtime_dependency(%q<puppetfile-resolver>.freeze, [">= 0.6.2".freeze, "< 1.0".freeze])
    s.add_runtime_dependency(%q<puppet-resource_api>.freeze, [">= 1.8.1".freeze])
    s.add_runtime_dependency(%q<r10k>.freeze, [">= 3.10".freeze, "< 6".freeze])
 -  s.add_runtime_dependency(%q<ruby_smb>.freeze, ["~> 1.0".freeze])
 +  s.add_runtime_dependency(%q<ruby_smb>.freeze, [">= 1.0".freeze])
-   s.add_runtime_dependency(%q<terminal-table>.freeze, [">= 3.0".freeze])
+   s.add_runtime_dependency(%q<terminal-table>.freeze, ["~> 4.0".freeze])
    s.add_runtime_dependency(%q<winrm>.freeze, ["~> 2.0".freeze])
    s.add_runtime_dependency(%q<winrm-fs>.freeze, ["~> 1.3".freeze])