diff --git a/www/rubygem-jekyll/Makefile b/www/rubygem-jekyll/Makefile
index 8539898f2b0c..dfec6544c4fe 100644
--- a/www/rubygem-jekyll/Makefile
+++ b/www/rubygem-jekyll/Makefile
@@ -2,28 +2,30 @@
 # $FreeBSD$
 
 PORTNAME=	jekyll
-PORTVERSION=	3.8.5
+PORTVERSION=	4.0.0
 CATEGORIES=	www rubygems
 MASTER_SITES=	RG
 
-MAINTAINER=	ruby@FreeBSD.org
+MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Simple, blog aware, static site generator
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	rubygem-addressable>=2.4:www/rubygem-addressable \
-		rubygem-colorator>=0.1:textproc/rubygem-colorator \
-		rubygem-em-websocket>=0.5:www/rubygem-em-websocket \
-		rubygem-i18n>=0.7:devel/rubygem-i18n \
-		rubygem-jekyll-sass-converter>=1.0:textproc/rubygem-jekyll-sass-converter \
-		rubygem-jekyll-watch>=2.0:www/rubygem-jekyll-watch \
-		rubygem-kramdown>=1.14:textproc/rubygem-kramdown \
-		rubygem-liquid>=4.0:textproc/rubygem-liquid \
-		rubygem-mercenary>=0.3.3:devel/rubygem-mercenary \
-		rubygem-pathutil>=0.9:devel/rubygem-pathutil \
-		rubygem-rouge>=1.7:textproc/rubygem-rouge \
-		rubygem-safe_yaml>=1.0:devel/rubygem-safe_yaml
+RUN_DEPENDS=	rubygem-addressable>=2.4<3:www/rubygem-addressable \
+		rubygem-colorator>=1.0<2:textproc/rubygem-colorator \
+		rubygem-em-websocket>=0.5<1:www/rubygem-em-websocket \
+		rubygem-i18n>=0.9.5,2<2,2:devel/rubygem-i18n \
+		rubygem-jekyll-sass-converter>=2.0<3:textproc/rubygem-jekyll-sass-converter \
+		rubygem-jekyll-watch>=2.0<3:www/rubygem-jekyll-watch \
+		rubygem-kramdown>=2.1<3:textproc/rubygem-kramdown \
+		rubygem-kramdown-parser-gfm>=1.0<2:textproc/rubygem-kramdown-parser-gfm \
+		rubygem-liquid>=4.0<5:textproc/rubygem-liquid \
+		rubygem-mercenary>=0.3.3<0.4:devel/rubygem-mercenary \
+		rubygem-pathutil>=0.9<1:devel/rubygem-pathutil \
+		rubygem-rouge>=3.0<4:textproc/rubygem-rouge \
+		rubygem-safe_yaml>=1.0<2:devel/rubygem-safe_yaml \
+		rubygem-terminal-table>=1.8<2:textproc/rubygem-terminal-table
 
 USES=		gem
 USE_RUBY=	yes
diff --git a/www/rubygem-jekyll/distinfo b/www/rubygem-jekyll/distinfo
index fad8171b933d..45b17cfeb131 100644
--- a/www/rubygem-jekyll/distinfo
+++ b/www/rubygem-jekyll/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1541431019
-SHA256 (rubygem/jekyll-3.8.5.gem) = 6316459a4524a971e2553f794d2e3ec66f4341ca8452153df855500406d3c2da
-SIZE (rubygem/jekyll-3.8.5.gem) = 112640
+TIMESTAMP = 1567842512
+SHA256 (rubygem/jekyll-4.0.0.gem) = 4a1dc48895d525bfb98cd562bf03ab6dd2727b5795360877c90e12670b9fec3a
+SIZE (rubygem/jekyll-4.0.0.gem) = 119808
diff --git a/www/rubygem-jekyll/files/patch-gemspec b/www/rubygem-jekyll/files/patch-gemspec
deleted file mode 100644
index ef9f193ef07a..000000000000
--- a/www/rubygem-jekyll/files/patch-gemspec
+++ /dev/null
@@ -1,11 +0,0 @@
---- jekyll.gemspec.orig	2018-02-14 14:08:19 UTC
-+++ jekyll.gemspec
-@@ -29,7 +29,7 @@ Gem::Specification.new do |s|
-       s.add_runtime_dependency(%q<addressable>.freeze, ["~> 2.4"])
-       s.add_runtime_dependency(%q<colorator>.freeze, ["~> 1.0"])
-       s.add_runtime_dependency(%q<em-websocket>.freeze, ["~> 0.5"])
--      s.add_runtime_dependency(%q<i18n>.freeze, ["~> 0.7"])
-+      s.add_runtime_dependency(%q<i18n>.freeze, [">= 0.7"])
-       s.add_runtime_dependency(%q<jekyll-sass-converter>.freeze, ["~> 1.0"])
-       s.add_runtime_dependency(%q<jekyll-watch>.freeze, ["~> 2.0"])
-       s.add_runtime_dependency(%q<kramdown>.freeze, ["~> 1.14"])