diff --git a/devel/rubygem-debug/Makefile b/devel/rubygem-debug/Makefile
index b12e6c430185..750e3dccb775 100644
--- a/devel/rubygem-debug/Makefile
+++ b/devel/rubygem-debug/Makefile
@@ -1,20 +1,20 @@
 PORTNAME=	debug
-DISTVERSION=	1.8.0
+DISTVERSION=	1.9.1
 CATEGORIES=	devel rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	yasu@FreeBSD.org
 COMMENT=	Debugging functionality for Ruby
 WWW=		https://rubygems.org/gems/debug
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
-RUN_DEPENDS=	rubygem-irb>=1.5.0:devel/rubygem-irb \
-		rubygem-reline>=0.3.1:devel/rubygem-reline
+RUN_DEPENDS=	rubygem-irb>=1.10<2:devel/rubygem-irb \
+		rubygem-reline>=0.3.8:devel/rubygem-reline
 
 USES=		gem
 
 PLIST_FILES=	bin/rdbg
 
 .include <bsd.port.mk>
diff --git a/devel/rubygem-debug/distinfo b/devel/rubygem-debug/distinfo
index 6a89a81bb6a0..48a329d6ca8e 100644
--- a/devel/rubygem-debug/distinfo
+++ b/devel/rubygem-debug/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1683675055
-SHA256 (rubygem/debug-1.8.0.gem) = 502bd1ad41a9a4b51f557f181cd13650c746390a82b5d11a5d2c81600ca013da
-SIZE (rubygem/debug-1.8.0.gem) = 97280
+TIMESTAMP = 1707349868
+SHA256 (rubygem/debug-1.9.1.gem) = 86f1a6d4a299184f1a1f7ae4c2fe80f178beed55cdf608f83b49d7bdefa3ffda
+SIZE (rubygem/debug-1.9.1.gem) = 98304