diff --git a/security/libressl-devel/Makefile b/security/libressl-devel/Makefile
index daa464c11003..5bd38d1c7d12 100644
--- a/security/libressl-devel/Makefile
+++ b/security/libressl-devel/Makefile
@@ -1,74 +1,74 @@
 PORTNAME=	libressl
-PORTVERSION=	4.2.0
+PORTVERSION=	4.2.1
 CATEGORIES=	security devel
 MASTER_SITES=	OPENBSD/LibreSSL
 PKGNAMESUFFIX=	-devel
 
 MAINTAINER=	brnrd@FreeBSD.org
 COMMENT=	Free version of the SSL/TLS protocol forked from OpenSSL
 WWW=		https://www.libressl.org/
 
 LICENSE=	BSD4CLAUSE
 LICENSE_FILE=	${WRKSRC}/COPYING
 
 FLAVORS=	default libtls
 FLAVOR?=	${FLAVORS:[1]}
 libtls_DESCR=	pkg-descr-libtls
 libtls_PKGNAMESUFFIX=	-devel-libtls
 libtls_PLIST=	pkg-plist-libtls
 
 CPE_VENDOR=	openbsd
 
 OPTIONS_DEFINE=	LIBTLS MAN3 NC
 OPTIONS_DEFAULT=	MAN3 NC
 LIBTLS_DESC=	Only install libtls (no libcrypto/libssl)
 MAN3_DESC=	Install API manpages (section 3)
 NC_DESC=	Install TLS-enabled netcat
 
 CONFLICTS_INSTALL=		libressl \
 				libretls
 default_CONFLICTS_INSTALL=	openssl openssl111 openssl3* openssl-quictls
 
 .if ${FLAVOR:U} == default
 OPTIONS_EXCLUDE=	LIBTLS
 .elif ${FLAVOR:U} == libtls
 OPTIONS_SLAVE=		LIBTLS
 OPTIONS_EXCLUDE=	MAN3
 .endif
 
 LIBTLS_CONFIGURE_ENABLE=	libtls-only
 NC_CONFIGURE_ENABLE=		nc
 
 GNU_CONFIGURE=	yes
 GNU_CONFIGURE_MANPREFIX=	${PREFIX}/share
 USES=		cpe libtool pathfix pkgconfig
 USE_LDCONFIG=	yes
 OPTIONS_SUB=	yes
 CFLAGS+=	-fpic -DPIC -Wl,-rpath,${PREFIX}/lib -Wl,--as-needed
 LDFLAGS+=	-pthread
 
 INSTALL_TARGET=	install-strip
 TEST_TARGET=	check
 
 PLIST_SUB+=	LIBCRYPTO_SHLIBMAJ=57 \
 		LIBCRYPTO_SHLIBFULL=57.0.1 \
 		LIBSSL_SHLIBMAJ=60 \
 		LIBSSL_SHLIBFULL=60.0.1 \
 		LIBTLS_SHLIBMAJ=33 \
 		LIBTLS_SHLIBFULL=33.0.1
 
 post-patch-MAN3-off:
 	${REINPLACE_CMD} -e '/^install-man:/s/install-man3//' \
 		-e '/$$(MAKE) $$(AM_MAKEFLAGS) install-data-hook/d' \
 		${WRKSRC}/man/Makefile.in
 
 post-install:
 	${RM} -r ${STAGEDIR}/${PREFIX}/etc/ssl/cert.pem
 	${RMDIR} ${STAGEDIR}${PREFIX}/etc/ssl/certs
 	${LN} -s /etc/ssl/certs ${STAGEDIR}${PREFIX}/etc/ssl/certs
 
 post-stage-MAN3-on:
 	(cd ${STAGEDIR}${PREFIX}; ${FIND} share/man/man3 -not -type d | \
 		${SED} 's/$$/.gz/' >> ${TMPPLIST})
 
 .include <bsd.port.mk>
diff --git a/security/libressl-devel/distinfo b/security/libressl-devel/distinfo
index 6971a8021c4e..c6306873f027 100644
--- a/security/libressl-devel/distinfo
+++ b/security/libressl-devel/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1760545157
-SHA256 (libressl-4.2.0.tar.gz) = 0f7dba44d7cb8df8d53f2cfbf1955254bc128e0089595f1aba2facfaee8408b2
-SIZE (libressl-4.2.0.tar.gz) = 9147132
+TIMESTAMP = 1761831840
+SHA256 (libressl-4.2.1.tar.gz) = 6d5c2f58583588ea791f4c8645004071d00dfa554a5bf788a006ca1eb5abd70b
+SIZE (libressl-4.2.1.tar.gz) = 9147769