diff --git a/devel/rubygem-datadog/Makefile b/devel/rubygem-datadog/Makefile
index a545f18ad89b..3f998c70b9bb 100644
--- a/devel/rubygem-datadog/Makefile
+++ b/devel/rubygem-datadog/Makefile
@@ -1,27 +1,27 @@
 PORTNAME=	datadog
-PORTVERSION=	2.25.0
+PORTVERSION=	2.27.0
 CATEGORIES=	devel rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Datadog's client library for Ruby
 WWW=		https://github.com/DataDog/dd-trace-rb
 
 LICENSE=	APACHE20 BSD3CLAUSE
 LICENSE_COMB=	dual
 LICENSE_FILE_APACHE20=	${WRKSRC}/LICENSE.Apache
 LICENSE_FILE_BSD3CLAUSE=${WRKSRC}/LICENSE.BSD3
 
-RUN_DEPENDS=	rubygem-datadog-ruby_core_source>=3.5.0<4:devel/rubygem-datadog-ruby_core_source \
-		rubygem-libdatadog>=24.0.1.1.0<24.0.1.2:devel/rubygem-libdatadog \
+RUN_DEPENDS=	rubygem-datadog-ruby_core_source>=3.5.1<4:devel/rubygem-datadog-ruby_core_source \
+		rubygem-libdatadog>=25.0.0.1.0<25.0.0.2:devel/rubygem-libdatadog \
 		rubygem-libddwaf>=1.30.0.0.0<1.30.0.1:devel/rubygem-libddwaf \
 		rubygem-logger>=0:devel/rubygem-logger \
 		rubygem-msgpack>=0:devel/rubygem-msgpack
 
 USES=		gem
 
 NO_ARCH=	yes
 
 PLIST_FILES=	bin/ddprofrb
 
 .include <bsd.port.mk>
diff --git a/devel/rubygem-datadog/distinfo b/devel/rubygem-datadog/distinfo
index 00eff99a189b..ac646d9ea322 100644
--- a/devel/rubygem-datadog/distinfo
+++ b/devel/rubygem-datadog/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1768626653
-SHA256 (rubygem/datadog-2.25.0.gem) = 6f7688588f8f19612932df7cd3b01c9db5bd8c4a124bef2197f7aced556d3342
-SIZE (rubygem/datadog-2.25.0.gem) = 753664
+TIMESTAMP = 1769875316
+SHA256 (rubygem/datadog-2.27.0.gem) = 64570e6073268b1cd65e3ef3a40c2817168ec05ff93965662d45b6dca0a74935
+SIZE (rubygem/datadog-2.27.0.gem) = 759808