diff --git a/sysutils/Makefile b/sysutils/Makefile
index f9f4cd8c4357..7ce82f8bc169 100644
--- a/sysutils/Makefile
+++ b/sysutils/Makefile
@@ -1155,6 +1155,7 @@
     SUBDIR += rubygem-chef-telemetry
     SUBDIR += rubygem-chef-utils
     SUBDIR += rubygem-chef-vault
+    SUBDIR += rubygem-chef-winrm
     SUBDIR += rubygem-chef-zero
     SUBDIR += rubygem-choria-mcorpc-support
     SUBDIR += rubygem-facter
diff --git a/sysutils/rubygem-chef-winrm/Makefile b/sysutils/rubygem-chef-winrm/Makefile
new file mode 100644
index 000000000000..d2169920eb22
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm/Makefile
@@ -0,0 +1,29 @@
+PORTNAME=	chef-winrm
+PORTVERSION=	2.3.11
+CATEGORIES=	sysutils rubygems
+MASTER_SITES=	RG
+
+MAINTAINER=	sunpoet@FreeBSD.org
+COMMENT=	Ruby library for Windows Remote Management
+WWW=		https://github.com/chef/chef-winrm
+
+LICENSE=	APACHE20
+LICENSE_FILE=	${WRKSRC}/LICENSE
+
+RUN_DEPENDS=	rubygem-builder>=2.1.2:devel/rubygem-builder \
+		rubygem-chef-gyoku>=1.4.1:textproc/rubygem-chef-gyoku \
+		rubygem-erubi>=1.8:www/rubygem-erubi \
+		rubygem-gssapi>=1.2<2:security/rubygem-gssapi \
+		rubygem-httpclient>=2.2.0.2<3:www/rubygem-httpclient \
+		rubygem-logging>=1.6.1<3.0:devel/rubygem-logging \
+		rubygem-nori>=2.7.0:devel/rubygem-nori \
+		rubygem-rexml>=3.3<4:textproc/rubygem-rexml \
+		rubygem-rubyntlm>=0.6.3<0.7:net/rubygem-rubyntlm
+
+USES=		gem
+
+NO_ARCH=	yes
+
+PLIST_FILES=	bin/rwinrm
+
+.include <bsd.port.mk>
diff --git a/sysutils/rubygem-chef-winrm/distinfo b/sysutils/rubygem-chef-winrm/distinfo
new file mode 100644
index 000000000000..3d67fecd9802
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm/distinfo
@@ -0,0 +1,3 @@
+TIMESTAMP = 1740022428
+SHA256 (rubygem/chef-winrm-2.3.11.gem) = 555e5e13a0e5724d0a5cdfa124ea4d4b2b6b9802fe46214beac8c2c33bbed26e
+SIZE (rubygem/chef-winrm-2.3.11.gem) = 42496
diff --git a/sysutils/rubygem-chef-winrm/files/patch-gemspec b/sysutils/rubygem-chef-winrm/files/patch-gemspec
new file mode 100644
index 000000000000..70169335efff
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm/files/patch-gemspec
@@ -0,0 +1,11 @@
+--- chef-winrm.gemspec.orig	2025-02-20 19:35:49 UTC
++++ chef-winrm.gemspec
+@@ -30,7 +30,7 @@ Gem::Specification.new do |s|
+   s.add_runtime_dependency(%q<gssapi>.freeze, ["~> 1.2".freeze])
+   s.add_runtime_dependency(%q<httpclient>.freeze, ["~> 2.2".freeze, ">= 2.2.0.2".freeze])
+   s.add_runtime_dependency(%q<logging>.freeze, [">= 1.6.1".freeze, "< 3.0".freeze])
+-  s.add_runtime_dependency(%q<nori>.freeze, ["= 2.7.0".freeze])
++  s.add_runtime_dependency(%q<nori>.freeze, [">= 2.7.0".freeze])
+   s.add_runtime_dependency(%q<rexml>.freeze, ["~> 3.3".freeze])
+   s.add_development_dependency(%q<pry>.freeze, [">= 0".freeze])
+   s.add_development_dependency(%q<rake>.freeze, [">= 10.3".freeze, "< 13".freeze])
diff --git a/sysutils/rubygem-chef-winrm/pkg-descr b/sysutils/rubygem-chef-winrm/pkg-descr
new file mode 100644
index 000000000000..9913d0583f94
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm/pkg-descr
@@ -0,0 +1,10 @@
+Windows Remote Management (WinRM) for Ruby
+
+This is a SOAP library that uses the functionality in Windows Remote
+Management(WinRM) to call native object in Windows. This includes, but is not
+limited to, running batch scripts, powershell scripts and fetching WMI
+variables.
+
+As of version 2.0, this gem retains the WinRM name but all powershell calls use
+the more modern Powershell Remoting Protocol (PSRP) for initializing runspace
+pools as well as creating and processing powershell pipelines.