diff --git a/sysutils/rubygem-chef-winrm/Makefile b/sysutils/rubygem-chef-winrm/Makefile
index db25e70ee590..fcb582ae3e8c 100644
--- a/sysutils/rubygem-chef-winrm/Makefile
+++ b/sysutils/rubygem-chef-winrm/Makefile
@@ -1,29 +1,29 @@
 PORTNAME=	chef-winrm
-PORTVERSION=	2.4.3
+PORTVERSION=	2.4.4
 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>=1.5<2: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
index 2cee9a6fef02..51e564d02d2d 100644
--- a/sysutils/rubygem-chef-winrm/distinfo
+++ b/sysutils/rubygem-chef-winrm/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1745936418
-SHA256 (rubygem/chef-winrm-2.4.3.gem) = 1a59dbf82b0ba91141ef460ba23739957f30b7e69ea073c0f1806058af05cbc9
-SIZE (rubygem/chef-winrm-2.4.3.gem) = 42496
+TIMESTAMP = 1755062614
+SHA256 (rubygem/chef-winrm-2.4.4.gem) = 7f6a54f2a36a6d4c1d426a7a0a350ca02e3056a8207e0e2dce9c1ad7796cade9
+SIZE (rubygem/chef-winrm-2.4.4.gem) = 42496