diff --git a/sysutils/Makefile b/sysutils/Makefile
index 7ce82f8bc169..4f3f26c503d4 100644
--- a/sysutils/Makefile
+++ b/sysutils/Makefile
@@ -1156,6 +1156,7 @@
     SUBDIR += rubygem-chef-utils
     SUBDIR += rubygem-chef-vault
     SUBDIR += rubygem-chef-winrm
+    SUBDIR += rubygem-chef-winrm-elevated
     SUBDIR += rubygem-chef-zero
     SUBDIR += rubygem-choria-mcorpc-support
     SUBDIR += rubygem-facter
diff --git a/sysutils/rubygem-chef-winrm-elevated/Makefile b/sysutils/rubygem-chef-winrm-elevated/Makefile
new file mode 100644
index 000000000000..f516d227676d
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm-elevated/Makefile
@@ -0,0 +1,21 @@
+PORTNAME=	chef-winrm-elevated
+PORTVERSION=	1.2.5
+CATEGORIES=	sysutils rubygems
+MASTER_SITES=	RG
+
+MAINTAINER=	sunpoet@FreeBSD.org
+COMMENT=	Ruby library for running commands via WinRM as elevated through a scheduled task
+WWW=		https://github.com/chef/chef-winrm-elevated
+
+LICENSE=	APACHE20
+LICENSE_FILE=	${WRKSRC}/LICENSE
+
+RUN_DEPENDS=	rubygem-chef-winrm>=2.3.11:sysutils/rubygem-chef-winrm \
+		rubygem-chef-winrm-fs>=1.3.7:filesystems/rubygem-chef-winrm-fs \
+		rubygem-erubi>=1.8:www/rubygem-erubi
+
+USES=		gem
+
+NO_ARCH=	yes
+
+.include <bsd.port.mk>
diff --git a/sysutils/rubygem-chef-winrm-elevated/distinfo b/sysutils/rubygem-chef-winrm-elevated/distinfo
new file mode 100644
index 000000000000..b330a7ac166a
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm-elevated/distinfo
@@ -0,0 +1,3 @@
+TIMESTAMP = 1740022430
+SHA256 (rubygem/chef-winrm-elevated-1.2.5.gem) = 9985b4eb1e5bbfbe1db9e4bbea29a5775ee9e6e7d52cfbb9787bcab605ff5807
+SIZE (rubygem/chef-winrm-elevated-1.2.5.gem) = 13312
diff --git a/sysutils/rubygem-chef-winrm-elevated/pkg-descr b/sysutils/rubygem-chef-winrm-elevated/pkg-descr
new file mode 100644
index 000000000000..582950d9fe5d
--- /dev/null
+++ b/sysutils/rubygem-chef-winrm-elevated/pkg-descr
@@ -0,0 +1,6 @@
+Runs PowerShell commands as elevated over Windows Remote Management (WinRM) via
+a scheduled task
+
+This gem allows you to break out of the magical WinRM constraints thus allowing
+to reach out to network shares and even install Windows updates, .NET, SQL
+Server etc.