diff --git a/sysutils/rubygem-chef/Makefile b/sysutils/rubygem-chef/Makefile
index 8477dc299072..f32a214633dc 100644
--- a/sysutils/rubygem-chef/Makefile
+++ b/sysutils/rubygem-chef/Makefile
@@ -1,59 +1,63 @@
 PORTNAME=	chef
-PORTVERSION=	18.9.4
+PORTVERSION=	19.1.164
 CATEGORIES=	sysutils
 MASTER_SITES=	RG
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Systems integration framework. Client part
 WWW=		https://www.chef.io/ \
 		https://github.com/chef/chef
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	rubygem-addressable>=0:www/rubygem-addressable \
 		rubygem-aws-sdk-s3>=1.91<2:devel/rubygem-aws-sdk-s3 \
 		rubygem-aws-sdk-secretsmanager>=1.46<2:devel/rubygem-aws-sdk-secretsmanager \
+		rubygem-bcrypt_pbkdf>=1.0<2:security/rubygem-bcrypt_pbkdf \
 		rubygem-chef-config>=${PORTVERSION}<${PORTVERSION}_99:sysutils/rubygem-chef-config \
+		rubygem-chef-licensing>=1.3<2:sysutils/rubygem-chef-licensing \
 		rubygem-chef-utils>=${PORTVERSION}<${PORTVERSION}_99:sysutils/rubygem-chef-utils \
 		rubygem-chef-vault>=0:sysutils/rubygem-chef-vault \
-		rubygem-chef-zero>=15.0.21<15.2:sysutils/rubygem-chef-zero \
+		rubygem-chef-zero>=15.1.0<15.2:sysutils/rubygem-chef-zero \
 		rubygem-corefoundation>=0.3.4<0.4:devel/rubygem-corefoundation \
-		rubygem-diff-lcs>=1.2.4:textproc/rubygem-diff-lcs \
+		rubygem-csv>=3.3.5<3.4:devel/rubygem-csv \
+		rubygem-diff-lcs>=1.6.0<1.7:textproc/rubygem-diff-lcs \
+		rubygem-ed25519>=1.2<2:security/rubygem-ed25519 \
 		rubygem-erubis>=2.7<3:www/rubygem-erubis \
-		rubygem-ffi>=1.15.5:devel/rubygem-ffi \
+		rubygem-ffi>=1.15.5<1.18.0:devel/rubygem-ffi \
 		rubygem-ffi-libarchive>=1.0.3<2:devel/rubygem-ffi-libarchive \
 		rubygem-ffi-yajl>=2.2<3:devel/rubygem-ffi-yajl \
 		rubygem-iniparse>=1.4<2:devel/rubygem-iniparse \
-		rubygem-inspec-core>=5<6:devel/rubygem-inspec-core \
+		rubygem-inspec-core>=7.0.95<7.1:devel/rubygem-inspec-core \
 		rubygem-license-acceptance>=1.0.5<3:sysutils/rubygem-license-acceptance \
 		rubygem-mixlib-archive>=0.4<2.0:devel/rubygem-mixlib-archive \
 		rubygem-mixlib-authentication>=2.1<4:devel/rubygem-mixlib-authentication \
 		rubygem-mixlib-cli>=2.1.1<3.0:devel/rubygem-mixlib-cli \
-		rubygem-mixlib-log>=2.0.3<3.2:devel/rubygem-mixlib-log \
-		rubygem-mixlib-shellout>=3.1.1<4.0:devel/rubygem-mixlib-shellout \
+		rubygem-mixlib-log>=2.0.3<4.0:devel/rubygem-mixlib-log \
+		rubygem-mixlib-shellout>=3.3.8<3.4:devel/rubygem-mixlib-shellout \
 		rubygem-net-ftp>=0:ftp/rubygem-net-ftp \
 		rubygem-net-sftp>=2.1.2<5.0:security/rubygem-net-sftp \
-		rubygem-ohai18>=18.0<19:sysutils/rubygem-ohai18 \
+		rubygem-ohai>=19.0<20:sysutils/rubygem-ohai \
 		rubygem-plist>=3.2<4:devel/rubygem-plist \
 		rubygem-proxifier2>=1.1<2:net/rubygem-proxifier2 \
+		rubygem-syslog>=0:devel/rubygem-syslog \
 		rubygem-syslog-logger>=1.6<2:sysutils/rubygem-syslog-logger \
 		rubygem-train-core>=3.13.4<4:net/rubygem-train-core \
 		rubygem-train-rest>=0.4.1:net/rubygem-train-rest \
 		rubygem-train-winrm>=0.2.17:net/rubygem-train-winrm \
-		rubygem-unf_ext>=0.0.8.2:textproc/rubygem-unf_ext \
-		rubygem-uri>=1.0.3:net/rubygem-uri \
-		rubygem-uuidtools>=2.1.5:devel/rubygem-uuidtools \
+		rubygem-unf_ext>=0.0.9.1:textproc/rubygem-unf_ext \
+		rubygem-uri>=1.0.4:net/rubygem-uri \
 		rubygem-vault>=0.18.2<1:security/rubygem-vault
 
 USES=		cpe gem
 
 NO_ARCH=	yes
 
 SUB_LIST=	RUBY=${RUBY}
 USE_RC_SUBR=	chef_client
 
 post-install:
 	${MKDIR} ${STAGEDIR}/var/chef
 
 .include <bsd.port.mk>
diff --git a/sysutils/rubygem-chef/distinfo b/sysutils/rubygem-chef/distinfo
index 78f125e9b408..ad4a2867fd8b 100644
--- a/sysutils/rubygem-chef/distinfo
+++ b/sysutils/rubygem-chef/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1768626719
-SHA256 (rubygem/chef-18.9.4.gem) = f4d31e7db0a8bf6de2f0db2d381f7a0a3dfc3181664e8fefe2b36383eed65e36
-SIZE (rubygem/chef-18.9.4.gem) = 891392
+TIMESTAMP = 1771421984
+SHA256 (rubygem/chef-19.1.164.gem) = a54d1a437038dd566dd33e660ca854de5e3219e53faf4df0f21510332d57d459
+SIZE (rubygem/chef-19.1.164.gem) = 909824
diff --git a/sysutils/rubygem-chef/files/patch-gemspec b/sysutils/rubygem-chef/files/patch-gemspec
index ba65ea9b3405..e444089c3c46 100644
--- a/sysutils/rubygem-chef/files/patch-gemspec
+++ b/sysutils/rubygem-chef/files/patch-gemspec
@@ -1,44 +1,17 @@
---- chef.gemspec.orig	2025-12-06 17:01:00 UTC
+--- chef.gemspec.orig	2026-02-19 07:08:41 UTC
 +++ chef.gemspec
-@@ -26,7 +26,7 @@ Gem::Specification.new do |s|
-   s.add_runtime_dependency(%q<chef-config>.freeze, ["= 18.8.54".freeze])
-   s.add_runtime_dependency(%q<chef-utils>.freeze, ["= 18.8.54".freeze])
-   s.add_runtime_dependency(%q<train-core>.freeze, ["~> 3.13".freeze, ">= 3.13.4".freeze])
--  s.add_runtime_dependency(%q<train-winrm>.freeze, ["~> 0.2.17".freeze])
-+  s.add_runtime_dependency(%q<train-winrm>.freeze, [">= 0.2.17".freeze])
-   s.add_runtime_dependency(%q<train-rest>.freeze, [">= 0.4.1".freeze])
-   s.add_runtime_dependency(%q<license-acceptance>.freeze, [">= 1.0.5".freeze, "< 3".freeze])
-   s.add_runtime_dependency(%q<mixlib-cli>.freeze, [">= 2.1.1".freeze, "< 3.0".freeze])
-@@ -36,12 +36,12 @@ Gem::Specification.new do |s|
-   s.add_runtime_dependency(%q<mixlib-archive>.freeze, [">= 0.4".freeze, "< 2.0".freeze])
-   s.add_runtime_dependency(%q<ohai>.freeze, ["~> 18.0".freeze])
-   s.add_runtime_dependency(%q<inspec-core>.freeze, [">= 5".freeze, "< 6".freeze])
--  s.add_runtime_dependency(%q<ffi>.freeze, [">= 1.15.5".freeze, "<= 1.16.3".freeze])
-+  s.add_runtime_dependency(%q<ffi>.freeze, [">= 1.15.5".freeze])
-   s.add_runtime_dependency(%q<ffi-yajl>.freeze, ["~> 2.2".freeze])
-   s.add_runtime_dependency(%q<net-sftp>.freeze, [">= 2.1.2".freeze, "< 5.0".freeze])
-   s.add_runtime_dependency(%q<net-ftp>.freeze, [">= 0".freeze])
-   s.add_runtime_dependency(%q<erubis>.freeze, ["~> 2.7".freeze])
--  s.add_runtime_dependency(%q<diff-lcs>.freeze, [">= 1.2.4".freeze, "!= 1.4.0".freeze, "< 1.6.0".freeze])
-+  s.add_runtime_dependency(%q<diff-lcs>.freeze, [">= 1.2.4".freeze, "!= 1.4.0".freeze])
-   s.add_runtime_dependency(%q<ffi-libarchive>.freeze, ["~> 1.0".freeze, ">= 1.0.3".freeze])
-   s.add_runtime_dependency(%q<chef-zero>.freeze, [">= 15.0.21".freeze])
-   s.add_runtime_dependency(%q<chef-vault>.freeze, [">= 0".freeze])
-@@ -49,13 +49,13 @@ Gem::Specification.new do |s|
-   s.add_runtime_dependency(%q<iniparse>.freeze, ["~> 1.4".freeze])
-   s.add_runtime_dependency(%q<addressable>.freeze, [">= 0".freeze])
+@@ -53,12 +53,12 @@ Gem::Specification.new do |s|
+   s.add_runtime_dependency(%q<csv>.freeze, ["~> 3.3.5".freeze])
    s.add_runtime_dependency(%q<syslog-logger>.freeze, ["~> 1.6".freeze])
--  s.add_runtime_dependency(%q<uuidtools>.freeze, [">= 2.1.5".freeze, "< 3.0".freeze])
--  s.add_runtime_dependency(%q<unf_ext>.freeze, ["~> 0.0.8.2".freeze])
--  s.add_runtime_dependency(%q<uri>.freeze, ["~> 1.0.3".freeze])
-+  s.add_runtime_dependency(%q<uuidtools>.freeze, [">= 2.1.5".freeze])
-+  s.add_runtime_dependency(%q<unf_ext>.freeze, [">= 0.0.8.2".freeze])
-+  s.add_runtime_dependency(%q<uri>.freeze, [">= 1.0.3".freeze])
+   s.add_runtime_dependency(%q<unf_ext>.freeze, ["~> 0.0.9.1".freeze])
+-  s.add_runtime_dependency(%q<uri>.freeze, ["~> 1.0.4".freeze])
++  s.add_runtime_dependency(%q<uri>.freeze, [">= 1.0.4".freeze])
    s.add_runtime_dependency(%q<corefoundation>.freeze, ["~> 0.3.4".freeze])
    s.add_runtime_dependency(%q<proxifier2>.freeze, ["~> 1.1".freeze])
    s.add_runtime_dependency(%q<aws-sdk-s3>.freeze, ["~> 1.91".freeze])
    s.add_runtime_dependency(%q<aws-sdk-secretsmanager>.freeze, ["~> 1.46".freeze])
 -  s.add_runtime_dependency(%q<vault>.freeze, ["~> 0.18.2".freeze])
 +  s.add_runtime_dependency(%q<vault>.freeze, ["~> 0.18".freeze, ">= 0.18.2".freeze])
+   s.add_runtime_dependency(%q<chef-licensing>.freeze, ["~> 1.3".freeze])
  end