diff --git a/www/rubygem-mechanize/Makefile b/www/rubygem-mechanize/Makefile
index cab7735ff133..c021620c6543 100644
--- a/www/rubygem-mechanize/Makefile
+++ b/www/rubygem-mechanize/Makefile
@@ -1,27 +1,30 @@
 # Created by: Cheng-Lung Sung <clsung@FreeBSD.org>
 
 PORTNAME=	mechanize
-PORTVERSION=	2.7.6
+PORTVERSION=	2.8.1
 CATEGORIES=	www rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	ruby@FreeBSD.org
 COMMENT=	WWW::Mechanize, a handy web browsing ruby object
 
 LICENSE=	MIT
-LICENSE_FILE=	${WRKSRC}/LICENSE.rdoc
+LICENSE_FILE=	${WRKSRC}/LICENSE.txt
 
-RUN_DEPENDS=	rubygem-domain_name>=0.5.1:net/rubygem-domain_name \
-		rubygem-http-cookie>=1.0.0:www/rubygem-http-cookie \
-		rubygem-mime-types>=2.0:misc/rubygem-mime-types \
-		rubygem-net-http-digest_auth>=1.1.1:www/rubygem-net-http-digest_auth \
-		rubygem-net-http-persistent>=2.5.2:www/rubygem-net-http-persistent \
-		rubygem-nokogiri>=1.4:textproc/rubygem-nokogiri \
-		rubygem-ntlm-http>=0.1.1:www/rubygem-ntlm-http \
-		rubygem-webrobots>=0.0.9:www/rubygem-webrobots
+RUN_DEPENDS=	rubygem-addressable>=2.7<3:www/rubygem-addressable \
+		rubygem-domain_name>=0.5.20190701<1:net/rubygem-domain_name \
+		rubygem-http-cookie>=1.0.3<2:www/rubygem-http-cookie \
+		rubygem-mime-types>=3.0<4:misc/rubygem-mime-types \
+		rubygem-net-http-digest_auth>=1.4.1<2:www/rubygem-net-http-digest_auth \
+		rubygem-net-http-persistent>=2.5.2<5.0:www/rubygem-net-http-persistent \
+		rubygem-nokogiri>=1.11.2<2:textproc/rubygem-nokogiri \
+		rubygem-rubyntlm>=0.6.3<1:net/rubygem-rubyntlm \
+		rubygem-webrick>=1.7<2:www/rubygem-webrick \
+		rubygem-webrobots>=0.1.2<0.2:www/rubygem-webrobots
 
-NO_ARCH=	yes
-USE_RUBY=	yes
 USES=		gem
+USE_RUBY=	yes
+
+NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/www/rubygem-mechanize/distinfo b/www/rubygem-mechanize/distinfo
index 10c9c4f840c6..a919d9181f63 100644
--- a/www/rubygem-mechanize/distinfo
+++ b/www/rubygem-mechanize/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1527942742
-SHA256 (rubygem/mechanize-2.7.6.gem) = 3d3318db3c66a27721b7cfcb0924464887e2737b6c120d401f0f196df6270301
-SIZE (rubygem/mechanize-2.7.6.gem) = 138752
+TIMESTAMP = 1626714748
+SHA256 (rubygem/mechanize-2.8.1.gem) = ca43d0c08538f5674429189e19a102fa67ff9b2c2af688c433ec05d764d616a4
+SIZE (rubygem/mechanize-2.8.1.gem) = 141312