diff --git a/www/tdiary/Makefile b/www/tdiary/Makefile
index fd5689e273b0..8ab6b70d3f21 100644
--- a/www/tdiary/Makefile
+++ b/www/tdiary/Makefile
@@ -1,103 +1,103 @@
 # Created by: Fumihiko Kimura <jfkimura@yahoo.co.jp>
 
 PORTNAME=	tdiary
-DISTVERSION=	5.2.0
+DISTVERSION=	5.2.1
 CATEGORIES?=	www ruby
 MASTER_SITES=	https://github.com/tdiary/tdiary-core/releases/download/v${PORTVERSION}/
 DISTNAME=	${PORTNAME}-full-v${PORTVERSION}
 
 MAINTAINER=	yasu@FreeBSD.org
 COMMENT=	Web-based diary system (like weblog) written in Ruby
 
 LICENSE=	GPLv2+
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	rubygem-bundler>=2.0.2:sysutils/rubygem-bundler \
 		rubygem-emot>=0.0.4:textproc/rubygem-emot \
-		rubygem-fastimage>=2.1.7:graphics/rubygem-fastimage \
+		rubygem-fastimage>=2.2.6:graphics/rubygem-fastimage \
 		rubygem-hikidoc>=0.1.0:textproc/rubygem-hikidoc \
 		rubygem-mail>=2.7.1:mail/rubygem-mail \
 		rubygem-rack>=2.2.3,3:www/rubygem-rack \
-		rubygem-rake>=12.3.3:devel/rubygem-rake
+		rubygem-rake>=13.0.6:devel/rubygem-rake
 
 USES=		cpe shebangfix
 USE_RUBY=	yes
 
 SHEBANG_FILES=	bin/tdiary index.fcgi index.rb misc/convert2.rb misc/migrate.rb \
 		misc/plugin/xmlrpc/xmlrpc.rb update.fcgi update.rb
 
 DOCSDIR=	${PREFIX}/share/doc/${PKGBASE}
 WWWDIR=		${PREFIX}/www/${PKGBASE}
 REINPLACE_ARGS=	-i ''
 NO_ARCH=	yes
 NO_BUILD=	yes
 SUB_FILES=	pkg-message tdiaryinst.rb
 SUB_LIST+=	TDIARY_LANG=${TDIARY_LANG} \
 		TDIARY_SCRIPT=${TDIARY_SCRIPT}
 
 WRKSRC=		${WRKDIR}/${PORTNAME}-v${PORTVERSION}
 PLIST_SUB=	TDIARY_SCRIPT=${TDIARY_SCRIPT} \
 		WWWGRP=${WWWGRP} \
 		WWWOWN=${WWWOWN}
 
 PORTDOCS=	${HTML} ${MD} ChangeLog doc.css
 
 OPTIONS_DEFINE=	DOCS
 
 DOCFILES=	HOWTO-authenticate-in-rack HOWTO-make-io HOWTO-make-plugin \
 		HOWTO-make-theme HOWTO-testing-tDiary HOWTO-use-plugin \
 		HOWTO-write-tDiary.en HOWTO-write-tDiary INSTALL-paas INSTALL \
 		README.en README UPGRADE
 HTML=		${DOCFILES:S/$/.html/}
 MD=		${DOCFILES:S/$/.md/}
 
 #TDIARY_LANG	ja:Japanese en:English
 .if !defined(TDIARY_LANG) || (defined(TDIARY_LANG) && ${TDIARY_LANG} != ja)
 TDIARY_LANG=	en
 .endif
 
 TDIARY_SCRIPT=	${PKGBASE}-inst.rb
 
 pre-patch:
 	@${RM} ${WRKSRC}/.coveralls.yml
 	@${RM} ${WRKSRC}/.dockerignore
 	@${RM} ${WRKSRC}/.editorconfig
 	@${RM} ${WRKSRC}/.gitignore
 	@${RM} ${WRKSRC}/.travis.yml
 	@${RM} ${WRKSRC}/Dockerfile
 	@${RM} ${WRKSRC}/Gemfile.lock
 	@${RM} ${WRKSRC}/Procfile
 	@${RM} ${WRKSRC}/Rakefile
 	@${RM} ${WRKSRC}/config.ru
 	@${RM} ${WRKSRC}/tdiary.gemspec
 	@${RM} ${WRKSRC}/tmp/.gitkeep
 	@${RM} -r ${WRKSRC}/.bundle
 	@${RM} -r ${WRKSRC}/.devcontainer
 	@${RM} -r ${WRKSRC}/.github
 	@${RM} -r ${WRKSRC}/.vscode
 	@${RM} -r ${WRKSRC}/misc/lib/bundler-2.2.18
 	@${RM} -r ${WRKSRC}/public
 	@${RM} -r ${WRKSRC}/spec
 	@${RM} -r ${WRKSRC}/test
 	@${RM} -r ${WRKSRC}/vendor
 	@${MV} ${WRKSRC}/ChangeLog ${WRKSRC}/doc
 	@${MV} ${WRKSRC}/README.md ${WRKSRC}/doc
 
 pre-install:
 	@${SED} -e 's,#!/usr/bin/env ruby,#!${RUBY},' \
 		${WRKDIR}/tdiaryinst.rb > ${WRKDIR}/${TDIARY_SCRIPT}
 	@${REINPLACE_CMD} 's!%%LOCALBASE%%!${LOCALBASE}!g' \
 		${WRKSRC}/misc/convert2.rb \
 		${WRKSRC}/misc/migrate.rb
 	@${FIND} ${WRKSRC} -name "*.orig" -delete
 
 do-install:
 	${INSTALL_SCRIPT} ${WRKDIR}/${TDIARY_SCRIPT} ${STAGEDIR}${PREFIX}/bin
 	@${MKDIR} ${STAGEDIR}${WWWDIR}
 	${TAR} --exclude doc --exclude LICENSE -C ${WRKSRC} -cf - . | ${TAR} --unlink -C ${STAGEDIR}${WWWDIR} -xf -
 
 do-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	cd ${WRKSRC}/doc && ${INSTALL_DATA} ${PORTDOCS} ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff --git a/www/tdiary/distinfo b/www/tdiary/distinfo
index ef7507ab635b..e28efd80c04c 100644
--- a/www/tdiary/distinfo
+++ b/www/tdiary/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1638281537
-SHA256 (tdiary-full-v5.2.0.tar.gz) = 08e80242f0c829209797e297fc508771e1915c854da04ca01f600a05cac1ad40
-SIZE (tdiary-full-v5.2.0.tar.gz) = 6904081
+TIMESTAMP = 1646059121
+SHA256 (tdiary-full-v5.2.1.tar.gz) = 21eb777508b117994a5edfb7f30c6386f43bc2a59d00e12df126c40263a9d677
+SIZE (tdiary-full-v5.2.1.tar.gz) = 7652079
diff --git a/www/tdiary/files/patch-Gemfile b/www/tdiary/files/patch-Gemfile
index 8778ca17174b..108fe7dc52f6 100644
--- a/www/tdiary/files/patch-Gemfile
+++ b/www/tdiary/files/patch-Gemfile
@@ -1,39 +1,38 @@
---- Gemfile.orig	2021-05-29 15:12:39 UTC
+--- Gemfile.orig	2022-02-28 12:02:31 UTC
 +++ Gemfile
-@@ -6,36 +6,3 @@ gem 'fastimage'
- gem 'emot'
+@@ -7,35 +7,3 @@ gem 'emot'
  gem 'mail'
+ gem 'net-smtp' # https://github.com/mikel/mail/pull/1439
  gem 'rake'
 -
 -group :development do
 -  gem 'pit', require: false
 -  gem 'racksh', require: false
 -  gem 'redcarpet'
 -  gem 'octokit'
 -  gem 'mime-types'
--  gem "ruby-debug-ide"
--  gem "debase"
+-  gem "debug"
 -
 -  group :test do
 -    gem 'test-unit'
 -    gem 'rspec'
 -    gem 'capybara', require: 'capybara/rspec'
--	 gem 'date', '>= 3.1.1' # for compatibility of capybara
+-    gem 'date', '>= 3.1.1' # for compatibility of capybara
 -    gem 'selenium-webdriver'
 -    gem 'launchy'
 -    gem 'sequel'
 -    gem 'sqlite3'
 -    gem 'jasmine', '< 3'
 -    gem 'simplecov', require: false
 -    gem 'coveralls', '~> 0.8', require: false
 -    gem "rexml"
 -    gem "webrick"
 -  end
 -end
 -
 -# https://github.com/redmine/redmine/blob/master/Gemfile#L89
 -local_gemfile = File.join(File.dirname(__FILE__), "Gemfile.local")
 -if File.exist?(local_gemfile)
 -  puts "Loading Gemfile.local ..." if $DEBUG # `ruby -d` or `bundle -v`
 -  instance_eval File.read(local_gemfile)
 -end