diff --git a/www/rubygem-rackup/Makefile b/www/rubygem-rackup/Makefile
index 4c7d9742aae9..7ee38e674b23 100644
--- a/www/rubygem-rackup/Makefile
+++ b/www/rubygem-rackup/Makefile
@@ -1,20 +1,20 @@
 PORTNAME=	rackup
-DISTVERSION=	2.0.0
+DISTVERSION=	2.1.0
 CATEGORIES=	www rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	yasu@FreeBSD.org
 COMMENT=	General server command for Rack applications
 WWW=		https://github.com/rack/rackup
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/license.md
 
 RUN_DEPENDS=	rubygem-rack>=3,3:www/rubygem-rack \
-		rubygem-webrick>0:www/rubygem-webrick
+		rubygem-webrick>=1.8<2:www/rubygem-webrick
 
 USES=		gem
 
 PLIST_FILES=	bin/rackup
 
 .include <bsd.port.mk>
diff --git a/www/rubygem-rackup/distinfo b/www/rubygem-rackup/distinfo
index c61f91668cbd..0ad65701d1fb 100644
--- a/www/rubygem-rackup/distinfo
+++ b/www/rubygem-rackup/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1674093198
-SHA256 (rubygem/rackup-2.0.0.gem) = b8e484fab8e7bad1883cd2722e13a1ed8c916db7201599280100ce926491ea37
-SIZE (rubygem/rackup-2.0.0.gem) = 14336
+TIMESTAMP = 1674819073
+SHA256 (rubygem/rackup-2.1.0.gem) = 6ecb884a581990332e45ee17bdfdc14ccbee46c2f710ae1566019907869a6c4d
+SIZE (rubygem/rackup-2.1.0.gem) = 15872