diff --git a/devel/rubygem-datadog-ci/Makefile b/devel/rubygem-datadog-ci/Makefile
index 018a0b1c1182..721694e9a69d 100644
--- a/devel/rubygem-datadog-ci/Makefile
+++ b/devel/rubygem-datadog-ci/Makefile
@@ -1,22 +1,22 @@
 PORTNAME=	datadog-ci
-PORTVERSION=	1.19.0
+PORTVERSION=	1.20.2
 CATEGORIES=	devel rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Datadog's Test Optimization library for Ruby
 WWW=		https://docs.datadoghq.com/continuous_integration/ \
 		https://github.com/DataDog/datadog-ci-rb
 
 LICENSE=	BSD3CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE.BSD3
 
 RUN_DEPENDS=	rubygem-datadog>=2.4<3:devel/rubygem-datadog \
 		rubygem-drb>=0:devel/rubygem-drb \
 		rubygem-msgpack>=0:devel/rubygem-msgpack
 
 USES=		gem
 
 PLIST_FILES=	bin/ddcirb
 
 .include <bsd.port.mk>
diff --git a/devel/rubygem-datadog-ci/distinfo b/devel/rubygem-datadog-ci/distinfo
index 3b244e8d966d..d456f3b3f850 100644
--- a/devel/rubygem-datadog-ci/distinfo
+++ b/devel/rubygem-datadog-ci/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1750188224
-SHA256 (rubygem/datadog-ci-1.19.0.gem) = fa62f0ef295c9e6224dbbb3245247b53ed7072c43e3cfe4562d55f04d8b5123f
-SIZE (rubygem/datadog-ci-1.19.0.gem) = 115200
+TIMESTAMP = 1752266216
+SHA256 (rubygem/datadog-ci-1.20.2.gem) = 0774ce76173c0f321e0afb2965e4e97c32b4cbe6dd5b79e603e0b7f3ae3a860b
+SIZE (rubygem/datadog-ci-1.20.2.gem) = 117760