diff --git a/sysutils/puppetserver8/Makefile b/sysutils/puppetserver8/Makefile
index c082a44f4875..71f67c8383be 100644
--- a/sysutils/puppetserver8/Makefile
+++ b/sysutils/puppetserver8/Makefile
@@ -1,92 +1,92 @@
 PORTNAME=	puppetserver
-PORTVERSION=	8.4.0
+PORTVERSION=	8.5.0
 CATEGORIES=	sysutils java
 MASTER_SITES=	https://downloads.puppetlabs.com/puppet/
 PKGNAMESUFFIX=	8
 
 MAINTAINER=	puppet@FreeBSD.org
 COMMENT=	Puppet Server running in the JVM
 WWW=		https://docs.puppetlabs.com/puppetserver/latest/services_master_puppetserver.html
 
 LICENSE=	APACHE20
 
 ONLY_FOR_ARCHS=	aarch64 amd64
 ONLY_FOR_ARCHS_REASON=Bundled JNI only support some architectures
 
 RUN_DEPENDS=	bash>=0:shells/bash \
 		puppet8>=8.0:sysutils/puppet8 \
 		rubygem-puppetserver-ca>=1:sysutils/rubygem-puppetserver-ca \
 		rubygem-semantic_puppet>=1:devel/rubygem-semantic_puppet \
 		sudo>=1:security/sudo
 
 USES=		ruby shebangfix
 USE_RC_SUBR=	puppetserver
 
 USE_JAVA=	yes
 NO_ARCH=	yes
 NO_BUILD=	yes
 JAVA_VERSION=	11+
 
 CONFLICTS_INSTALL=	puppetserver[0-9]
 
 SHEBANG_FILES=	ext/bin/puppetserver
 
 USERS=		puppet
 GROUPS=		puppet
 
 SUB_LIST=	JAVA_HOME=${JAVA_HOME}
 SUB_FILES=	pkg-message
 
 post-patch:
 .for file in ext/config/logback.xml ext/config/request-logging.xml \
 	ext/config/conf.d/global.conf ext/config/conf.d/puppetserver.conf \
 	ext/config/conf.d/web-routes.conf ext/config/conf.d/webserver.conf \
 	ext/config/conf.d/auth.conf ext/config/services.d/ca.cfg \
 	ext/system-config/services.d/bootstrap.cfg ext/bin/puppetserver \
 	ext/cli_defaults/cli-defaults.sh ext/cli/foreground
 	@${REINPLACE_CMD} -e 's|%%PREFIX%%|${PREFIX}|' \
 		-e 's|%%RUBY_SITELIBDIR%%|${RUBY_SITELIBDIR}|' \
 		-e 's|%%RUBY_VER%%|${RUBY_VER}|' \
 		-e 's|%%JAVA%%|${JAVA}|' \
 		-e 's|%%ETCDIR%%|${ETCDIR}|' \
 		-e 's|%%DATADIR%%|${DATADIR}|' \
 		${WRKSRC}/${file}
 .endfor
 	@${REINPLACE_CMD} -e 's|#!/opt/puppetlabs/puppet/bin/ruby|#!${RUBY}|' \
 		${WRKSRC}/ext/cli/ca \
 		${WRKSRC}/ext/cli/dropsonde
 
 do-install:
 	@${MKDIR} ${STAGEDIR}${DATADIR}/cli/apps
 	@${MKDIR} ${STAGEDIR}${ETCDIR}/conf.d
 	@${MKDIR} ${STAGEDIR}${ETCDIR}/services.d
 	@${MKDIR} ${STAGEDIR}${PREFIX}/etc/puppet/code
 	@${MKDIR} ${STAGEDIR}/var/log/puppetserver
 	@${MKDIR} ${STAGEDIR}/var/puppet/server
 	@${MKDIR} ${STAGEDIR}/var/puppet/server/data
 	@${MKDIR} ${STAGEDIR}/var/puppetserver
 	@${MKDIR} ${STAGEDIR}/var/run/puppetserver
 	${INSTALL_DATA} ${WRKSRC}/puppet-server-release.jar ${STAGEDIR}${DATADIR}/puppet-server-release.jar
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/global.conf ${STAGEDIR}${ETCDIR}/conf.d/global.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/logback.xml ${STAGEDIR}${ETCDIR}/logback.xml.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/request-logging.xml ${STAGEDIR}${ETCDIR}/request-logging.xml.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/puppetserver.conf ${STAGEDIR}${ETCDIR}/conf.d/puppetserver.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/web-routes.conf ${STAGEDIR}${ETCDIR}/conf.d/web-routes.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/webserver.conf ${STAGEDIR}${ETCDIR}/conf.d/webserver.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/auth.conf ${STAGEDIR}${ETCDIR}/conf.d/auth.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/conf.d/metrics.conf ${STAGEDIR}${ETCDIR}/conf.d/metrics.conf.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/config/services.d/ca.cfg ${STAGEDIR}${ETCDIR}/services.d/ca.cfg.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/system-config/services.d/bootstrap.cfg ${STAGEDIR}${ETCDIR}/services.d/bootstrap.cfg.sample
 	${INSTALL_DATA} ${WRKSRC}/ext/bin/puppetserver ${STAGEDIR}${PREFIX}/bin/puppetserver
 	${INSTALL_DATA} ${WRKSRC}/ext/ezbake-functions.sh ${STAGEDIR}${DATADIR}/ezbake-functions.sh
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/ca ${STAGEDIR}${DATADIR}/cli/apps/ca
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/foreground ${STAGEDIR}${DATADIR}/cli/apps/foreground
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/gem ${STAGEDIR}${DATADIR}/cli/apps/gem
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/irb ${STAGEDIR}${DATADIR}/cli/apps/irb
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/reload ${STAGEDIR}${DATADIR}/cli/apps/reload
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/ruby ${STAGEDIR}${DATADIR}/cli/apps/ruby
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/start ${STAGEDIR}${DATADIR}/cli/apps/start
 	${INSTALL_DATA} ${WRKSRC}/ext/cli/stop ${STAGEDIR}${DATADIR}/cli/apps/stop
 	${INSTALL_DATA} ${WRKSRC}/ext/cli_defaults/cli-defaults.sh ${STAGEDIR}${DATADIR}/cli/cli-defaults.sh
 
 .include <bsd.port.mk>
diff --git a/sysutils/puppetserver8/distinfo b/sysutils/puppetserver8/distinfo
index 20b8d62f112e..00ca4cbcf0fb 100644
--- a/sysutils/puppetserver8/distinfo
+++ b/sysutils/puppetserver8/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1705780917
-SHA256 (puppetserver-8.4.0.tar.gz) = c7594ee33a71876e2a5fdae4624e9c576fb95a3789f8e2b3b9b37912b2a8c511
-SIZE (puppetserver-8.4.0.tar.gz) = 63830828
+TIMESTAMP = 1709278795
+SHA256 (puppetserver-8.5.0.tar.gz) = 9adca8fd495df85f6541841b4d50d16e831767f9619eeed88782a370eca778ec
+SIZE (puppetserver-8.5.0.tar.gz) = 64463953