diff --git a/www/tdiary/Makefile b/www/tdiary/Makefile
index db01cdc3447b..e80b8d33048e 100644
--- a/www/tdiary/Makefile
+++ b/www/tdiary/Makefile
@@ -2,7 +2,7 @@
 # $FreeBSD$
 
 PORTNAME=	tdiary
-PORTVERSION=	5.0.7
+PORTVERSION=	5.0.8
 CATEGORIES?=	www ruby
 MASTER_SITES=	https://github.com/tdiary/tdiary-core/releases/download/v${PORTVERSION}/
 DISTNAME=	${PORTNAME}-full-v${PORTVERSION}
@@ -18,8 +18,8 @@ RUN_DEPENDS=	rubygem-bundler>=1.16.1:sysutils/rubygem-bundler \
 		rubygem-fastimage>=2.1.1:graphics/rubygem-fastimage \
 		rubygem-hikidoc>=0.1.0:textproc/rubygem-hikidoc \
 		rubygem-mail>=2.7.0:mail/rubygem-mail \
-		rubygem-rack16>=1.6.8:www/rubygem-rack16 \
-		rubygem-rake>=12.1.0:devel/rubygem-rake
+		rubygem-rack>=2.0.4:www/rubygem-rack \
+		rubygem-rake>=12.3.1:devel/rubygem-rake
 
 USES=		shebangfix
 USE_RUBY=	yes
diff --git a/www/tdiary/distinfo b/www/tdiary/distinfo
index 2053553223fa..0785416f88ee 100644
--- a/www/tdiary/distinfo
+++ b/www/tdiary/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1515579444
-SHA256 (tdiary-full-v5.0.7.tar.gz) = 9cf1846f3012fa7488658354e72b1026d419dbe3e06f40993e4ad42eacab496d
-SIZE (tdiary-full-v5.0.7.tar.gz) = 7457096
+TIMESTAMP = 1522317812
+SHA256 (tdiary-full-v5.0.8.tar.gz) = fb94b3225f508e935755f2ddd0cc8681ce397311d7112f129f62cb635054b269
+SIZE (tdiary-full-v5.0.8.tar.gz) = 7031207
diff --git a/www/tdiary/files/patch-Gemfile b/www/tdiary/files/patch-Gemfile
index 6d3975794b16..0a3fa913bc7a 100644
--- a/www/tdiary/files/patch-Gemfile
+++ b/www/tdiary/files/patch-Gemfile
@@ -1,4 +1,4 @@
---- Gemfile.orig	2017-12-29 12:13:03 UTC
+--- Gemfile.orig	2018-03-29 10:07:52 UTC
 +++ Gemfile
 @@ -6,40 +6,3 @@ gem 'fastimage'
  gem 'emot'
@@ -29,9 +29,9 @@
 -    gem 'launchy'
 -    gem 'sequel'
 -    gem 'sqlite3'
--    gem 'jasmine'
+-    gem 'jasmine', '< 3'
 -    gem 'simplecov', require: false
--    gem 'coveralls', '~> 0.7.12', require: false
+-    gem 'coveralls', require: false
 -  end
 -end
 -
diff --git a/www/tdiary/pkg-plist b/www/tdiary/pkg-plist
index 2ce5c5d771a9..a8dbf5aa8e17 100644
--- a/www/tdiary/pkg-plist
+++ b/www/tdiary/pkg-plist
@@ -103,6 +103,9 @@ bin/%%TDIARY_SCRIPT%%
 %%WWWDIR%%/lib/tdiary/view.rb
 %%WWWDIR%%/lib/tdiary/view_helper.rb
 %%WWWDIR%%/misc/convert2.rb
+%%WWWDIR%%/misc/docker-devel/Dockerfile
+%%WWWDIR%%/misc/docker-devel/README.md
+%%WWWDIR%%/misc/docker-devel/run-app.sh
 %%WWWDIR%%/misc/filter/antispamservice.rb
 %%WWWDIR%%/misc/filter/limitdays.rb
 %%WWWDIR%%/misc/filter/linkcheck.rb