diff --git a/devel/rubygem-datadog/Makefile b/devel/rubygem-datadog/Makefile
index e171405190f7..7be3098bb3ed 100644
--- a/devel/rubygem-datadog/Makefile
+++ b/devel/rubygem-datadog/Makefile
@@ -1,27 +1,27 @@
 PORTNAME=	datadog
-PORTVERSION=	2.20.0
+PORTVERSION=	2.21.0
 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>=3.4.1<4:devel/rubygem-datadog-ruby_core_source \
 		rubygem-libdatadog>=18.1.0.1.0<18.1.0.2:devel/rubygem-libdatadog \
-		rubygem-libddwaf>=1.24.1.1.0<1.24.1.2:devel/rubygem-libddwaf \
+		rubygem-libddwaf>=1.24.1.2.1<1.24.1.3: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 b456b4766c5a..8e9d99c7ec24 100644
--- a/devel/rubygem-datadog/distinfo
+++ b/devel/rubygem-datadog/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1757436613
-SHA256 (rubygem/datadog-2.20.0.gem) = 11ab4f419cccb04132d8d12d762d184123fb8e2d792da61c811cee5b128aadb4
-SIZE (rubygem/datadog-2.20.0.gem) = 686592
+TIMESTAMP = 1759816856
+SHA256 (rubygem/datadog-2.21.0.gem) = 2364d02ab6cb13c0a6c0825ca710e1a909bab014d94b174f2107b0c5ab7aeb4f
+SIZE (rubygem/datadog-2.21.0.gem) = 691200