diff --git a/security/zaproxy/Makefile b/security/zaproxy/Makefile
index 4ead5886e9e8..4e92038c9f9a 100644
--- a/security/zaproxy/Makefile
+++ b/security/zaproxy/Makefile
@@ -1,76 +1,77 @@
 PORTNAME=	zaproxy
 DISTVERSIONPREFIX=	v
 DISTVERSION=	2.14.0
+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
 
 USES=		gettext-runtime
 USE_JAVA=	yes
 
 USE_GITHUB=	yes
 
 JAVA_VERSION=	11
 
 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}
 
 .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 \
 		--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/ && ${COPYTREE_SHARE} "db lang lib license plugin README scripts xml zap-${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 0648bfdd5661..1205a06c49d7 100644
--- a/security/zaproxy/distinfo
+++ b/security/zaproxy/distinfo
@@ -1,7 +1,7 @@
-TIMESTAMP = 1697561594
-SHA256 (zaproxy-2.14.0-deps.tar.gz) = b26f5ed89c10de95b3cb1d39224c8cb9f4e154b3a78c0bcc75106c152c2d9feb
-SIZE (zaproxy-2.14.0-deps.tar.gz) = 332187220
-SHA256 (zaproxy-2.14.0-plugins.tar.gz) = d6ca3c5179347c02c2addad85c9f29758143e2aaf5bb9c4e6752684982daef0c
-SIZE (zaproxy-2.14.0-plugins.tar.gz) = 232482983
+TIMESTAMP = 1711238273
+SHA256 (zaproxy-2.14.0-deps.tar.gz) = 961ed29f92d165bd06ed8b54821760fbf339069f80a6e26d3c9d77ea3fa0f2d2
+SIZE (zaproxy-2.14.0-deps.tar.gz) = 369588532
+SHA256 (zaproxy-2.14.0-plugins.tar.gz) = 93d2f25beecd882ea8af173665372faab82c0b8c1e0389e3dbededc2909e3517
+SIZE (zaproxy-2.14.0-plugins.tar.gz) = 232482946
 SHA256 (zaproxy-zaproxy-v2.14.0_GH0.tar.gz) = e775b827f2c1aa8ed93dae5c2677399fedbe8c64cbdd21e0122c3799706ca0ea
 SIZE (zaproxy-zaproxy-v2.14.0_GH0.tar.gz) = 5541732
diff --git a/security/zaproxy/files/patch-zap_src_main_java_org_parosproxy_paros_Constant.java b/security/zaproxy/files/patch-zap_src_main_java_org_parosproxy_paros_Constant.java
new file mode 100644
index 000000000000..31a1e2f23177
--- /dev/null
+++ b/security/zaproxy/files/patch-zap_src_main_java_org_parosproxy_paros_Constant.java
@@ -0,0 +1,23 @@
+--- zap/src/main/java/org/parosproxy/paros/Constant.java.orig	2024-03-24 00:03:43 UTC
++++ zap/src/main/java/org/parosproxy/paros/Constant.java
+@@ -1405,9 +1405,19 @@ public final class Constant {
+         return matcher.find();
+     }
+ 
++    // Determine FreeBSD Operating System
++    // ZAP: Changed to final.
++    private static final Pattern patternFreeBSD = Pattern.compile("freebsd", Pattern.CASE_INSENSITIVE);
++
++    public static boolean isFreeBSD() {
++        String os_name = System.getProperty("os.name");
++        Matcher matcher = patternFreeBSD.matcher(os_name);
++        return matcher.find();
++    }
++
+     // Determine Linux Operating System
+     // ZAP: Changed to final.
+-    private static final Pattern patternLinux = Pattern.compile("linux", Pattern.CASE_INSENSITIVE);
++    private static final Pattern patternLinux = Pattern.compile("linux|freebsd", Pattern.CASE_INSENSITIVE);
+ 
+     public static boolean isLinux() {
+         String os_name = System.getProperty("os.name");