diff --git a/security/zaproxy/Makefile b/security/zaproxy/Makefile
index eeb7640a5f82..da927a975d06 100644
--- a/security/zaproxy/Makefile
+++ b/security/zaproxy/Makefile
@@ -1,74 +1,75 @@
 PORTNAME=	zaproxy
 DISTVERSIONPREFIX=	v
 DISTVERSION=	2.16.0
+PORTREVISION=	1
 CATEGORIES=	security java
 
 MAINTAINER=	acm@FreeBSD.org
 COMMENT=	The zed attack proxy
 WWW=		https://www.zaproxy.org/
 
 LICENSE=	APACHE20
 
-BUILD_DEPENDS=	gradle:devel/gradle
+BUILD_DEPENDS=	gradle8:devel/gradle8
 
 USES=		gettext-runtime java
 USE_GITHUB=	yes
-JAVA_VERSION=	17
+JAVA_VERSION=	22
 
 NO_ARCH=	yes
 
 MAKE_ENV+=	GRADLE_USER_HOME=${WRKDIR}
 
 DESKTOP_ENTRIES="ZAP" "Zed Attack Proxy" "${PREFIX}/share/pixmaps/zaproxy.png" "${PORTNAME}" \
 		"System;Security;" true
 
 # to rebuild the deps archive:
 #   1. set DEV_UPDATE_MODE=yes
 #   2. make makesum build
 #   3. upload the *-deps archive
 #   4. set DEV_UPDATE_MODE=no
 #   5. make clean makesum
 
 DEV_UPDATE_MODE=	no
 
 DEPS_CACHE_DIR=	${WRKDIR}
 EXCLUDE_TASK=	--exclude-task :zap:downloadMainAddOns
 
 MAKE_ENV+=	JAVA_HOME=${JAVA_HOME}
 SUB_LIST=	JAVA_HOME=${JAVA_HOME}
 SUB_FILES=	pkg-message
 
 .if (${DEV_UPDATE_MODE} == "yes")
 EXCLUDE_TASK=	#
 post-build:
 	@cd ${DEPS_CACHE_DIR} && ${TAR} czf ${DISTDIR}/${DIST_SUBDIR}/${PORTNAME}-${DISTVERSION}-deps${EXTRACT_SUFX} gradle-${PORTNAME}
 	@cd ${WRKSRC}/zap/build && ${TAR} czf ${DISTDIR}/${DIST_SUBDIR}/${PORTNAME}-${DISTVERSION}-plugins${EXTRACT_SUFX} mainAddOns
 	@${ECHO} "(!!!) Please upload the deps archive: ${DISTDIR}/${DIST_SUBDIR}/${PORTNAME}-${DISTVERSION}-deps${EXTRACT_SUFX}"
 	@${ECHO} "(!!!) Please upload the plugins archive: ${DISTDIR}/${DIST_SUBDIR}/${PORTNAME}-${DISTVERSION}-plugins${EXTRACT_SUFX}"
 .else
 MASTER_SITES+=	LOCAL/acm/${PORTNAME}:deps
 DISTFILES+=	${PORTNAME}-${DISTVERSION}-deps${EXTRACT_SUFX}:deps \
 		${PORTNAME}-${DISTVERSION}-plugins${EXTRACT_SUFX}:deps
 GRADLE_ARGS=	--offline
 
 post-extract: # need a separate extract step because the cache is in /tmp, and not under work/ like with maven
 	@cd ${DEPS_CACHE_DIR} && ${TAR} xzf ${DISTDIR}/${DIST_SUBDIR}/${PORTNAME}-${DISTVERSION}-deps${EXTRACT_SUFX}
 
 post-patch:
 	@${REINPLACE_CMD} -e 's|%%JAVAJARDIR%%|${JAVAJARDIR}|g' \
 		-e 's|%%JAVA_HOME%%|${JAVA_HOME}|g' \
 		-e 's|%%VERSION%%|${DISTVERSION}|g' ${WRKSRC}/zap/src/main/dist/zap.sh
 .endif
 
 do-build:
-	cd ${WRKSRC} && ${SETENV} ${MAKE_ENV} gradle \
+	cd ${WRKSRC} && ${SETENV} ${MAKE_ENV} gradle8 \
 		--gradle-user-home ${DEPS_CACHE_DIR}/gradle-${PORTNAME} --project-cache-dir ${DEPS_CACHE_DIR}/gradle-${PORTNAME} \
 		${GRADLE_ARGS} --build-cache :zap:distCore ${EXCLUDE_TASK}
 
 do-install:
 	${INSTALL_SCRIPT} ${WRKSRC}/zap/build/distFiles/zap.sh ${STAGEDIR}${PREFIX}/bin/${PORTNAME}
 	cd ${WRKSRC}/zap/build/distFiles/ && ${COPYTREE_SHARE} "db lang lib license plugin README xml zap-${DISTVERSION}.jar" ${STAGEDIR}${JAVAJARDIR}/${PORTNAME}
 	cd ${WRKDIR}/mainAddOns && ${COPYTREE_SHARE} ./ ${STAGEDIR}${JAVAJARDIR}/${PORTNAME}/plugin
 	${INSTALL_DATA} ${WRKSRC}/zap/src/main/resources/resource/zap64x64.png ${STAGEDIR}${PREFIX}/share/pixmaps/zaproxy.png
 
 .include <bsd.port.mk>
diff --git a/security/zaproxy/distinfo b/security/zaproxy/distinfo
index c359e09feab6..9a9989ab8e4c 100644
--- a/security/zaproxy/distinfo
+++ b/security/zaproxy/distinfo
@@ -1,7 +1,7 @@
-TIMESTAMP = 1737348690
-SHA256 (zaproxy-2.16.0-deps.tar.gz) = 6e8fdcfda3dbd6519da2289d94627b9c23424f9e785a0daa63370f60733567bf
-SIZE (zaproxy-2.16.0-deps.tar.gz) = 372707670
-SHA256 (zaproxy-2.16.0-plugins.tar.gz) = 3cc459c3dd8cd8607c9daad382a7d927aa738317a2e101bf1e010d5a479636c2
-SIZE (zaproxy-2.16.0-plugins.tar.gz) = 256047886
+TIMESTAMP = 1738481973
+SHA256 (zaproxy-2.16.0-deps.tar.gz) = ead772faba54374d46676e43144cf744402287cca7e9744cfcce24fc1b053668
+SIZE (zaproxy-2.16.0-deps.tar.gz) = 310305400
+SHA256 (zaproxy-2.16.0-plugins.tar.gz) = b86790c74019c6c9744aa6f45fbde1c6f828a36304f75a9a52d21fdff3a6e758
+SIZE (zaproxy-2.16.0-plugins.tar.gz) = 256048760
 SHA256 (zaproxy-zaproxy-v2.16.0_GH0.tar.gz) = 1266d3fb657743293cca7b353d6acbae313d07d03e2d22daedc48849baa9a5b5
 SIZE (zaproxy-zaproxy-v2.16.0_GH0.tar.gz) = 5581869