diff --git devel/artifactory/Makefile devel/artifactory/Makefile
index 18b9f9a9e97f..bf30c6b723e0 100644
--- devel/artifactory/Makefile
+++ devel/artifactory/Makefile
@@ -1,7 +1,7 @@
 # $FreeBSD$
 
 PORTNAME=	artifactory
-PORTVERSION=	5.4.1
+PORTVERSION=	5.8.3
 CATEGORIES=	devel java
 MASTER_SITES=	https://bintray.com/artifact/download/jfrog/artifactory/
 DISTNAME=	jfrog-${PORTNAME}-oss-${PORTVERSION}
diff --git devel/artifactory/distinfo devel/artifactory/distinfo
index c5b0cf7bd564..b0e3f83c819d 100644
--- devel/artifactory/distinfo
+++ devel/artifactory/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1498280216
-SHA256 (jfrog-artifactory-oss-5.4.1.zip) = fcca958e005b7b4216667cee2e166aec85279f39c6ffb84e973906257f164dbd
-SIZE (jfrog-artifactory-oss-5.4.1.zip) = 76844845
+TIMESTAMP = 1516806922
+SHA256 (jfrog-artifactory-oss-5.8.3.zip) = c84e19779b3a7e62b86fdd3a71ba6b975838ac4f4531379d284290cc28637461
+SIZE (jfrog-artifactory-oss-5.8.3.zip) = 92381086
diff --git devel/artifactory/pkg-plist devel/artifactory/pkg-plist
index b88fe19346e6..55a4f5912f17 100644
--- devel/artifactory/pkg-plist
+++ devel/artifactory/pkg-plist
@@ -34,10 +34,11 @@
 %%APP_HOME%%/misc/tomcat/NGNIX.txt
 %%APP_HOME%%/misc/tomcat/artifactory.httpd.conf
 %%APP_HOME%%/misc/tomcat/artifactory.xml
-%%APP_HOME%%/misc/tomcat/index.html
 %%APP_HOME%%/misc/tomcat/logging.properties
 %%APP_HOME%%/misc/tomcat/server.xml
 %%APP_HOME%%/misc/tomcat/web.xml
+%%APP_HOME%%/misc/tomcat/webapps/ROOT/WEB-INF/rewrite.config
+%%APP_HOME%%/misc/tomcat/webapps/ROOT/index.html
 %%APP_HOME%%/misc/%%APP_HOME%%.config.template.yml
 %%APP_HOME%%/tomcat/LICENSE
 %%APP_HOME%%/tomcat/NOTICE
@@ -65,6 +66,8 @@
 %%APP_HOME%%/tomcat/conf/catalina.policy
 %%APP_HOME%%/tomcat/conf/catalina.properties
 %%APP_HOME%%/tomcat/conf/context.xml
+%%APP_HOME%%/tomcat/conf/jaspic-providers.xml
+%%APP_HOME%%/tomcat/conf/jaspic-providers.xsd
 %%APP_HOME%%/tomcat/conf/logging.properties
 %%APP_HOME%%/tomcat/conf/server.xml
 %%APP_HOME%%/tomcat/conf/web.xml
@@ -72,6 +75,7 @@
 %%APP_HOME%%/tomcat/lib/catalina.jar
 %%APP_HOME%%/tomcat/lib/derby-10.11.1.1.jar
 %%APP_HOME%%/tomcat/lib/el-api.jar
+%%APP_HOME%%/tomcat/lib/jaspic-api.jar
 %%APP_HOME%%/tomcat/lib/servlet-api.jar
 %%APP_HOME%%/tomcat/lib/tomcat-api.jar
 %%APP_HOME%%/tomcat/lib/tomcat-coyote.jar
@@ -86,6 +90,7 @@
 %%APP_HOME%%/webapps/access.war
 @owner artifactory
 @group artifactory
+%%VARDIR%%/tomcat/webapps/ROOT/WEB-INF/rewrite.config
 %%VARDIR%%/tomcat/webapps/ROOT/index.html
 %%VARDIR%%/etc/artifactory.config.xml
 %%VARDIR%%/etc/artifactory.system.properties
@@ -93,6 +98,7 @@
 %%VARDIR%%/etc/mimetypes.xml
 %%VARDIR%%/etc/logback.xml
 @dir %%VARDIR%%/tomcat/work
+@dir %%VARDIR%%/tomcat/webapps/ROOT/WEB-INF
 @dir %%VARDIR%%/tomcat/webapps/ROOT
 @dir %%VARDIR%%/tomcat/webapps
 @dir %%VARDIR%%/tomcat/temp